The Winterfell Huis Clos


Here is the brief encounter of Theon with the hooded man of Winterfell.
 When they found themselves face-to-face their eyes met briefly. The man put a hand on his dagger. “Theon Turncloak. Theon Kinslayer.”
“I’m not. I never ... I was ironborn.”
“False is all you were. How is it you still breathe?”
“The gods are not done with me,” Theon answered, wondering if this could be the killer, the night walker who had stuffed Yellow Dick’s cock into his mouth and pushed Roger Ryswell’s groom off the battlements. Oddly, he was not afraid. He pulled the glove from his left hand. “Lord Ramsay is not done with me.”
The man looked, and laughed. “I leave you to him, then.”
(A Ghost in Winterfell, ADwD)

We have discussed the notion that the hooded man had just arrived in the castle when he met Theon. We have discussed why Theon did not recognize the man, just like he did not recognize a Bolton guard in the final stage the escape: in reason of the hood, the heavy snow, and perhaps his general ineptitude at face recognition.

We had already discussed at length the kinslayer accusation, and how it points to the miller's sons, Wex and Robett Glover.

We are going to try to examine how and why the hooded man is in the castle. Since there is no given reason for the existence of a secret passage, and no given reason for the hooded man to have scaled the Wall, we are left to assume that the man entered by a normal entrance.

We are going to discuss again Little Walder's murder, which happened on the same night.

Unfortunately, I could not come up with a compelling story that would tie together the entrance of the hooded man, his complicity with the conspirators, his role in the dissension among Roose's allies, and the murder of Little Walder.

  1. Entrance
  2. In the Great Hall
  3. In the Solar
  4. News brought to Winterfell?
  5. The Escape
  6. The devoted Squire
  7. Ramsay's Day before the Escape
  8. What has happened?

1. Entrance

Two days before the encounter with Theon, we learned about the state of Winterfell's gates.
Winterfell’s great main gates were closed and barred, and so choked with ice and snow that the portcullis would need to be chipped free before it could be raised. Much the same was true of the Hunter’s Gate, though there at least ice was not a problem, since the gate had seen recent use. The Kingsroad Gate had not, and ice had frozen those drawbridge chains rock hard. Which left the Battlements Gate, a small arched postern in the inner wall. Only half a gate, in truth, it had a drawbridge that spanned the frozen moat but no corresponding gateway through the outer wall, offering access to the outer ramparts but not the world beyond.
(A Ghost in Winterfell, ADwD)
We had been warned before.
Every gate was closed and barred and heavily guarded, though; no one was allowed to enter or depart the castle without Lord Bolton’s leave.
(The Turncloak, ADwD)
And again.
Lord Bolton had Winterfell sewn up tight as a babe’s swaddling clothes. No one could come or go without his leave.
(A Ghost in Winterfell, ADwD)
So nobody comes in the castle at this point. We have been told a day before that.
“To fight Lord Stannis we would first need to find him,” Roose Ryswell pointed out. “Our scouts go out the Hunter’s Gate, but of late, none of them return.”
(A Ghost in Winterfell, ADwD)

Given that Crowfood greenboys are out of the castle digging traps, it means that the outriders have been ambushed by Mors' men. Since the hooded man managed to get in, he must have had Mors' leave, which is well in line with our remarks about their common use of the word kinslayer.

One can wonder about a secret passage. Bran knows that there is a secret tunnel in the inner Wall.
And he knew you could get inside the inner wall by the south gate, climb three floors and run all the way around Winterfell through a narrow tunnel in the stone, and then come out on ground level at the north gate, with a hundred feet of wall looming over you. Even Maester Luwin didn’t know that, Bran was convinced.
(Bran II, AGoT)

Such a passage seems to be of little help to get inside the castle. In any case, it doesn't help to get across the outer Wall. One could wonder if there is a passage through the crypts. Neither Ramsay when he put the castle to the torch, nor Roose when he came to restore the place seems to have ever paid any attention to the crypts. Since the Dreadfort has crypts as well, it would be surprising if Roose were fooled by such a possibility. We don't know whether Roose is aware of Barbrey Dustin's visit with Theon. In any case, Roose did not have the entrance of the cryptes guarded. He might be entirely unaware of the crypts, since his ally Barbrey Dustin could not locate the entrance.

Let's assume that the man has entered the castle by the Hunter's Gate. The man does not seem to have sneaked in. Indeed, he spoke to Theon on his own volition, and wouldn't have had he wanted to remain discreet.

Furthermore, Theon meets the man on his way out of the Great Hall. The snow has limited circulation to the trenches in Winterfell: He found himself alone in a white wilderness, walls of snow looming up to either side of him chest high. In other words, Theon is in a corridor. This is further confirmed by the fact that : Farther on, he came upon a man striding in the opposite direction, a hooded cloak flapping behind him. The use of the phrase the opposite direction (definite article) seems to indicate that there is no alternative to going forward and backward. However, the phrase farther on is unfortunately vague, and does not rule out that Theon has walked some distance.

We have some further understanding of the system of trenches during the escape the next day.
Not ten yards from the door, Rowan dropped her empty pail, and her sisters did likewise. The Great Keep was already lost to sight behind them. The yard was a white wilderness, full of half-heard sounds that echoed strangely amidst the storm. The icy trenches rose around them, knee high, then waist high, then higher than their heads. They were in the heart of Winterfell with the castle all around them, but no sign of it could be seen. They might have easily been lost amidst the Land of Always Winter, a thousand leagues beyond the Wall. “It’s cold,” Jeyne Poole whimpered as she stumbled along at Theon’s side.
And soon to be colder. Beyond the castle walls, winter was waiting with its icy teeth. If we get that far. “This way,” he said when they came to a junction where three trenches crossed.
“Frenya, Holly, go with them,” Rowan said. “We will be along with Abel. Do not wait for us.” And with that, she whirled and plunged into the snow, toward the Great Hall. Willow and Myrtle hurried after her, cloaks snapping in the wind.
(Theon, ADwD)

At the junction where the three trenches meet, one can go to the Great Hall, or to the Great Keep or towards other places, which include the Battlement Gate. Apparently at the junction, one can not hear clearly the sounds, and it is doubtful that Theon could still have heard the sad, soft song that Abel was singing the previous night when Theon had just left the Great Hall.

The natural understanding seems to be that the man can hardly go anywhere but to the Great Hall.

Hence, the man is not paying a clandestine visit to Winterfell. However, he does not wear any distinctive mark, while Theon is able to identify most men by the badge of their house (Tallhart, Cerwyn, Hornwood, Flint, Frey etc). Not wearing such a mark is suspicious. Roose has set watchers everywhere in Winterfell as we understand from Theon.
“I am told you have been wandering the castle,” Lord Bolton began. “Men have reported seeing you in the stables, in the kitchens, in the barracks, on the battlements. You have been observed near the ruins of collapsed keeps, outside Lady Catelyn’s old sept, coming and going from the godswood. Do you deny it?”
(A Ghost in Winterfell, ADwD)

Since the way to the Great Hall is a well frequented passage, I don't see any possibility for the hooded man to be paying a secret visit to Winterfell. The absence of identification mark, and the precautions currently taken by Roose because of the recent murders, make unlikely that he could melt into the crowd.

The hooded man is striding in the passages, despite the current conditions in Winterfell.
White walls rose to either side as he and Rowan made their way to the godswood; the paths between keep and tower and hall had turned into a maze of icy trenches, shoveled out hourly to keep them clear. It was easy to get lost in that frozen labyrinth, but Theon Greyjoy knew every twist and turning.
(Theon, ADwD)
Hence the hooded man seems to be familiar with the castle.

The hooded man wears only a dagger as he is about to enter the Hall. This is in accordance with the rule edicted by Roose.
No longswords had been allowed within the hall, but every man there wore a dagger, even Theon Greyjoy.
(The Prince of Winterfell, ADwD)

If the hooded man came into the castle secretly, how could he know about Roose's rule? His sword was probably left at the entrance of the castle. (The rule is violated all the time by Ramsay, and at least once by the Freys.)

In this scenario, I find unnatural, but not impossible, that no Bolton man came with the hooded man to announce the arrival to the lord.

Hence we are left with the notion that the man is going to the Great Hall, without any apprehension to meet the Warden of the North.

The hooded man's entrance to the castle might have been prepared by an incident that happened two days before.
“The gods have turned against us,” old Lord Locke was heard to say in the Great Hall. “This is their wroth. A wind as cold as hell itself and snows that never end. We are cursed.”
“Stannis is cursed,” a Dreadfort man insisted. “He is the one out there in the storm.”
“Lord Stannis might be warmer than we know,” one foolish freerider argued. “His sorceress can
summon fire. Might be her red god can melt these snows.”
That was unwise, Theon knew at once. The man spoke too loudly, and in the hearing of Yellow Dick and Sour Alyn and Ben Bones. When the tale reached Lord Ramsay, he sent his Bastard’s Boys to seize the man and drag him out into the snow. “As you seem so fond of Stannis, we will send you to him,” he said. Damon Dance-for-Me gave the freerider a few lashes with his long greased whip. Then, whilst Skinner and Yellow Dick made wagers on how fast his blood would freeze, Ramsay had the man dragged up to the Battlements Gate.
The bleeding freerider was carried across the bridge and up the steps, still protesting. Then Skinner and Sour Alyn seized his arms and legs and tossed him from the wall to the ground eighty feet below. The drifts had climbed so high that they swallowed the man bodily ... but bowmen on the battlements claimed they glimpsed him sometime later, dragging a broken leg through the snow. One feathered his rump with an arrow as he wriggled away. “He will be dead within the hour,” Lord Ramsay promised.
“Or he’ll be sucking Lord Stannis’s cock before the sun goes down,” Whoresbane Umber threw back.
(The Ghost of Winterfell, ADwD)

Whoresbane does not believe that Stannis is that close to Winterfell. However, Mors Umber might be, since the Ryswell scouts are said to be disappearing. The poor freerider might have ended up with Crowfood. There he might have reported the tensions inside the castle and the current anxiety about Stannis' arrival. This might have played a role in Crowfood's choice of tactic. It might  have been precious information for the hooded man as well. Beside the general atmosphere inside the castle, there is little that the freerider could have reported to Crowfood.

2. In the Great Hall

Here is the state of the Great Hall before Theon left the place to come across the hooded man.
The reek within the Great Hall was palpable by eventide. With hundreds of horses, dogs, and men squeezed underneath one roof, the floors slimy with mud and melting snow, horseshit, dog turds,
and even human feces, the air redolent with the smells of wet dog, wet wool, and sodden horse blankets, there was no comfort to be found amongst the crowded benches, but there was food. The cooks served up great slabs of fresh horsemeat, charred outside and bloody red within, with roast onions and neeps ... and for once, the common soldiers ate as well as the lords and knights.
The horsemeat was too tough for the ruins of Theon’s teeth. His attempts to chew gave him excruciating pain. So he mashed the neeps and onions up together with the flat of his dagger and made a meal of that, then cut the horse up very small, sucked on each piece, and spat it out. That way at least he had the taste, and some nourishment from the grease and blood. The bone was beyond him, though, so he tossed it to the dogs and watched Grey Jeyne make off with it whilst Sara and Willow snapped at her heels.
Lord Bolton commanded Abel to play for them as they ate. The bard sang “Iron Lances,” then “The Winter Maid.” When Barbrey Dustin asked for something more cheerful, he gave them “The Queen Took Off Her Sandal, the King Took Off His Crown,” and “The Bear and the Maiden Fair.” The Freys joined the singing, and even a few northmen slammed their fists on the table to the chorus, bellowing, “A bear! A bear!” But the noise frightened the horses, so the singers soon let off and the music died away.
(A Ghost in Winterfell, ADwD)

So a certain confusion reigns in the Hall, because of the necessity to accomodate the horses. But we know that Lord Bolton can see the whole of the Hall from the dais. He could see Abel in the back of the hall, in the proximity of horses.
He turned his head, his pale cold eyes searching the hall until they found the bard Abel beside Theon. “Singer,” he called, “come sing us something soothing.”
(Theon, ADwD)

The notion that the hooded man could come discreetly to the Great Hall seems unlikely to me. In particular, we have been told what is the standard behavior for those who enter the place.
Men entering the hall huddled by the fires or clapped their hands together over glowing braziers as their cloaks hung dripping from pegs inside the door.
(The Turncloak, ADwD)

Hence, it is unnatural to keep a cloak inside the hall. We can infer that, if the hooded man kept his cloak after entering the building, it was at the risk of attracting attention. Probably he did not keep it.

We know who was in the Great Hall: Roose Bolton, Barbrey Dustin, Abel, the Freys (does the definite article imply the presence of Hosteen, Aenys, and the Walders?). More noticeable people could have been in attendance as well. However, Ramsay was not present, as the following scene shows.
The Bastard’s Boys gathered beneath a wall sconce where a torch was flaming smokily. Luton and Skinner were throwing dice. Grunt had a woman in his lap, a breast in his hand. Damon Dance-for-Me sat greasing up his whip. “Reek,” he called. He tapped the whip against his calf as a man might do to summon his dog. “You are starting to stink again, Reek.”
Theon had no reply for that beyond a soft “Yes.”
“Lord Ramsay means to cut your lips off when all this is done,” said Damon, stroking his whip with a greasy rag.
My lips have been between his lady’s legs. That insolence cannot go un-punished. “As you say.” Luton guffawed. “I think he wants it.”
“Go away, Reek,” Skinner said. “The smell of you turns my stomach.” The others laughed.
He fled quickly, before they changed their minds. His tormentors would not follow him outside. Not so long as there was food and drink within, willing women and warm fires. As he left the hall, Abel was singing “The Maids That Bloom in Spring.”
(A Ghost in Winterfell, ADwD)

A few more things are worthy of notice. A few northmen joined the singing with the Freys. It seems to point to a certain goodwill between the northmen and the men of the riverlands, in spite of the Red Wedding.

Evidently, Barbrey Dustin is in a good mood at this point.

3. In the Solar

After meeting with the hooded man, Theon has wandered in the castle for a few hours.
Theon trudged through the storm until his arms and legs were caked with snow and his hands and feet had gone numb from cold, then climbed to the battlements of the inner wall again. Up here, a hundred feet high, a little wind was blowing, stirring the snow. All the crenels had filled up. Theon had to punch through a wall of snow to make a hole ... only to find that he could not see beyond the moat. Of the outer wall, nothing remained but a vague shadow and a few dim lights floating in the dark.

(A Ghost in Winterfell, ADwD)

We noted already the dim lights on the outer Wall. This is remarkable, since we have been told that the guards gather in the towers to stay warm.

Then Theon is summoned by Roose.
Theon returned to his own chambers. He was stripping off his wet clothes when Steelshanks Walton found him. “Come with me, turncloak. His lordship wants words with you.”
(A Ghost in Winterfell, ADwD)

The next scene seems the continuation of what happened in the Great Hall after the visit of the hooded man.
He had no clean dry clothes, so he wriggled back into the same damp rags and followed. Steelshanks led him back to the Great Keep and the solar that had once been Eddard Stark’s. Lord Bolton was not alone. Lady Dustin sat with him, pale-faced and severe; an iron horsehead brooch clasped Roger Ryswell’s cloak; Aenys Frey stood near the fire, pinched cheeks flushed with cold.
“I am told you have been wandering the castle,” Lord Bolton began. “Men have reported seeing you in the stables, in the kitchens, in the barracks, on the battlements. You have been observed near the ruins of collapsed keeps, outside Lady Catelyn’s old sept, coming and going from the godswood. Do you deny it?”
“No, m’lord.” Theon made sure to muddy up the word. He knew that pleased Lord Bolton. “I cannot sleep, m’lord. I walk.” He kept his head down, fixed upon the old stale rushes scattered on the floor. It was not wise to look his lordship in the face.
“I was a boy here before the war. A ward of Eddard Stark.”
“You were a hostage,” Bolton said. “Yes, m’lord. A hostage.”
It was my home, though. Not a true home, but the best I ever knew.
“Someone has been killing my men.”
“Yes, m’lord.”
“Not you, I trust?” Bolton’s voice grew even softer. “You would not repay all my kindnesses with such treachery.”
“No, m’lord, not me. I wouldn’t. I ... only walk, is all.” Lady Dustin spoke up. “Take off your gloves.”
Theon glanced up sharply. “Please, no. I ... I ...”
“Do as she says,” Ser Aenys said. “Show us your hands.”
Theon peeled his gloves off and held his hands up for them to see.
It is not as if I stand before them naked. It is not so bad as that. His left hand had three fingers, his right four. Ramsay had taken only the pinky off the one, the ring finger and forefingers from the other.
“The Bastard did this to you,” Lady Dustin said. “If it please m’lady, I ... I asked it of him.” Ramsay always made him ask. Ramsay always makes me beg.
“Why would you do that?”
“I ... I did not need so many fingers.”
“Four is enough.” Ser Aenys Frey fingered the wispy brown beard that sprouted from his weak chin like a rat’s tail. “Four on his right hand. He could still hold a sword. A dagger.”
Lady Dustin laughed. “Are all Freys such fools? Look at him. Hold a dagger? He hardly has the strength to hold a spoon. Do you truly think he could have overcome the Bastard’s disgusting creature and shoved his manhood down his throat?”
“These dead were all strong men,” said Roger Ryswell, “and none of them were stabbed. The turncloak’s not our killer.”
Roose Bolton’s pale eyes were fixed on Theon, as sharp as Skinner’s flaying knife. “I am inclined to agree. Strength aside, he does not have it in him to betray my son.”
Roger Ryswell grunted. “If not him, who? Stannis has some man inside the castle, that’s plain.”
Reek is no man. Not Reek. Not me. He wondered if Lady Dustin had told them about the crypts, the missing swords.
“We must look at Manderly,” muttered Ser Aenys Frey. “Lord Wyman loves us not.”
Ryswell was not convinced. “He loves his steaks and chops and meat pies, though. Prowling the castle by dark would require him to leave the table. The only time he does that is when he seeks the privy for one of his hourlong squats.”
“I do not claim Lord Wyman does the deeds himself. He brought three hundred men with him. A hundred knights. Any of them might have—”
“Night work is not knight’s work,” Lady Dustin said. “And Lord Wyman is not the only man who lost kin at your Red Wedding, Frey. Do you imagine Whoresbane loves you any better? If you did not hold the Greatjon, he would pull out your entrails and make you eat them, as Lady Hornwood ate her fingers. Flints, Cerwyns, Tallharts, Slates ... they all had men with the Young Wolf.”
“House Ryswell too,” said Roger Ryswell. “Even Dustins out of Barrowton.” Lady Dustin parted her lips in a thin, feral smile. “The north remembers, Frey.”
Aenys Frey’s mouth quivered with outrage. “Stark dishonored us. That is what you northmen had best remember.”
Roose Bolton rubbed at his chapped lips. “This squabbling will not serve.” He flicked his fingers at Theon. “You are free to go. Take care where you wander. Else it might be you we find upon the morrow, smiling a red smile.”
“As you say, m’lord.” Theon drew his gloves on over his maimed hands and took his leave, limping on his maimed foot.
(A Ghost in Winterfell, ADwD)

We shall note first who is present: Roose Bolton, Barbrey Dustin, Roger Ryswell, Aenys Frey. This is Roose's inner circle. Manderly, Hother Umber are not invited. The most noticeable absence is Ramsay's. But it is not surprising. Ramsay was a pariah in Barrowton.
“It should have been you who threw the feast, to welcome me back,” Ramsay complained, “and it should have been in Barrow Hall, not this pisspot of a castle.”
“Barrow Hall and its kitchens are not mine to dispose of,” his father said mildly. “I am only a guest there. The castle and the town belong to Lady Dustin, and she cannot abide you.”
(Reek III, ADwD)
Roose held a war council while Ramsay was occupied by his wedding night.
“The hall is not the place for such discussions, my lords. Let us adjourn to the solar whilst my son consummates his marriage. The rest of you, remain and enjoy the food and drink.”
(The Prince of Winterfell, ADwD)
This very day, Ramsay has disobeyed his father by divulging Yellow Dick's death.
“Burn the body,” Roose Bolton ordered, “and see that you do not speak of this. I’ll not have this tale spread.”
The tale spread nonetheless. By midday most of Winterfell had heard, many from the lips of Ramsay Bolton, whose “boy” Yellow Dick had been.
(A Ghost in Winterfell, ADwD)

A few remarks. Aenys Frey stood near the fire, pinched cheeks flushed with cold. He seems to come from outside. We are told they the Freys sang in the Great Hall just before the hooded man entered. However, there is an indoor passage reserved to the lord between the Great Keep and the Great Hall. It might simply mean that Aenys was not allowed to take the passage. In any case he did not remain continuously with Roose and Barbrey.

Since Roger Ryswell wears his cloak, he possibly came from outside as well.

Barbrey Dustin is pale-faced and severe. Her mood has changed since the previous scene in the Great Hall just before Theon came across the hooded man.
Lord Bolton commanded Abel to play for them as they ate. The bard sang “Iron Lances,” then “The Winter Maid.” When Barbrey Dustin asked for something more cheerful, he gave them “The Queen Took Off Her Sandal, the King Took Off His Crown,” and “The Bear and the Maiden Fair.” The Freys joined the singing, and even a few northmen slammed their fists on the table to the chorus, bellowing, “A bear! A bear!” But the noise frightened the horses, so the singers soon let off and the music died away.
(A Ghost in Winterfell, ADwD)

This is confirmed by the conversation. Her body language, she sat with [Roose], suggests sympathy and solidarity towards Lord Bolton.

Let's turn to the conversation.

Roger Ryswell mentions the Lord Wyman's lengthy visits to the privy, which suggests, in view of what happened in White Harbor, that Manderly has used the pretext to meet someone secretly.

The command addressed to Theon to show his hands is very interesting and seems to echo the meeting with the hooded man. I tend to believe that Theon showed his hand, not because the man was special to him, but because he felt he had to defend himself after the man has put the hand on the dagger and threatened him. The man has seen the hand and heard that Ramsay has crippled Theon.

It is widely known that Theon has been skinned here and there by Ramsay. But the mutilation is not common knowledge. And Theon hides his missing parts, out of shame. It's likely that Barbrey is aware of Theon's state, since she had him dressed for the wedding and had hosted him in Barrowton. But Aenys Frey might not be aware of the extent of Theon's plight. Both Barbrey and Aenys ask to see Theon's hands. It's as if they had discussed the matter just before Theon's arrival, following, we can guess, a mention by the hooded man, either in Aenys' presence or repeated to Aenys.

Another detail might allude to a conversation with the man. When Theon says he was once a ward in Winterfell, Roose corrects him: he was a hostage. It's what Roose could have objected, or simply thought, if someone had stated in his presence that Theon is a kinslayer. (For Roose, of course, kinslaying is defined by blood relations, but he could have understood another meaning in someone else.)

The most interesting aspect of the scene is the behavior of Barbrey Dustin, supported apparently by Roger Ryswell. First she insists heavily on Ramsay's cruelty, uses the dreaded word bastard, in the presence of Roose. But we already knew that she hated Ramsay, and she called Ramsay a bastard in a private conversation with Roose in Barrowton. That shows that Ramsay is not respected in the circle around Roose. Whether Barbrey's dislike for Ramsay is currently reaching new heights is unclear. At any rate, Roose does not object to have Ramsay treated with disrespect in presence of a third party.

We come to the most important issue. Barbrey suddenly raised the issue of the Red Wedding, in Roose's presence. But she put all the blame on the Freys. Previously, Barbrey had mentioned that Walda could become Roose's queen.
“Truth be told,” she said, “Lord Bolton aspires to more than mere lordship. Why not King of the North? Tywin Lannister is dead, the Kingslayer is maimed, the Imp is fled. The Lannisters are a spent force, and you were kind enough to rid him of the Starks. Old Walder Frey will not object to his fat little Walda becoming a queen. White Harbor might prove troublesome should Lord Wyman survive this coming battle ... but I am quite sure that he will not. No more than Stannis. Roose will remove both of them, as he removed the Young Wolf. Who else is there?”
(The Prince of Winterfell, ADwD)

She says plainly that Roose Bolton is responsible for Robb Stark's demise. So her attitude has changed. Roose said in Barrowton that Barbrey would remain loyal to him if a Stark boy were to resurface.
Roose made a face, as if the ale he was sipping had suddenly gone sour. “There are times you make me wonder if you truly are my seed. My forebears were many things, but never fools. No, be quiet now, I have heard enough. We appear strong for the moment, yes. We have powerful friends in the Lannisters and Freys, and the grudging support of much of the north ... but what do you imagine is going to happen when one of Ned Stark’s sons turns up?”
“Stark’s little wolflings are dead,” said Ramsay, sloshing some more ale into his cup, “and they’ll stay dead. Let them show their ugly faces, and my girls will rip those wolves of theirs to pieces. The sooner they turn up, the sooner I kill them again.”
The elder Bolton sighed. “Again? Surely you misspeak. You never slew Lord Eddard’s sons, those two sweet boys we loved so well. That was Theon Turncloak’s work, remember? How many of our grudging friends do you imagine we’d retain if the truth were known? Only Lady Barbrey, whom you would turn into a pair of boots ... inferior boots. Human skin is not as tough as cowhide and will not wear as well. By the king’s decree you are now a Bolton. Try and act like one. Tales are told of you, Ramsay. I hear them everywhere. People fear you.”
(Reek III, ADwD)

Roose didn't say anything about Barbrey's reaction if she were to know all the truth about the Red Wedding (recall that Roose had taken the precaution to spare at least some men from Barrowton and the Rills before the wedding). The hostility of Barbrey, and to some extent of Roger Ryswell, towards the Freys can be contrasted with their pacific and conciliatory attitude two days before, as the Manderlys and Freys were on the brink of armed hostility.
“Step out into the yard, you sack of suet, and I’ll serve you all the bloody bits that you can stomach,” Ser Hosteen said.
Wyman Manderly laughed, but half a dozen of his knights were on their feet at once. It fell to Roger Ryswell and Barbrey Dustin to calm them with quiet words.
(A Ghost in Winterfell, ADwD)

I have discussed already the severe mistrust between Ramsay and the Freys. By telling the Freys that they are not welcome in the north and by underlining the cruelty of Ramsay, Barbrey is likely to increase the tension for the inheritance of the Dreadfort.

Roose ends the conversation by attempting to calm the situation, which seems increasingly out of control. Barbrey, the Freys and Ramsay are mutually incompatible allies now. That might contribute to Roose's decision the next day: sending the Freys in the snow to fight Stannis, hoping thus to get rid of two problems at once (and a third problem: Manderly).

It is the last time we see Barbrey Dustin. In particular, she is not present during the last scene in the great hall, where every other character of note is present (except maester Henly, and a few Ryswells). It is likely to be significant, but in what sense?

4. News brought to Winterfell?

Let's return now to the hooded man. I tend to conclude from all this that the man met at least Barbrey and Roose, and brought news calculated to drive a wedge between the Dustin/Ryswells and the Freys.

Judging from the conversation, it might be about the Red Wedding.

The notion that the north could be appeased, and the Red Wedding be forgiven, by sacrificing the Freys has been put forward by Qyburn, Roose's old friend.
“A little spittle on Lord Walder’s tomb is not like to disturb the grave worms,” Qyburn agreed, “but it would also be useful if someone were to be punished for the Red Wedding. A few Frey heads would do much to mollify the north.”
(Cersei IV, AFfC)
That could explain the decision taken the next day by Roose to send the Frey to battle Stannis.

The responsability of Roose Bolton in the Red Wedding is not well known, it seems. We don't know what Roose's official line is. The Freys maintain that the Young Wolf turned into a real wolf.
The Lord of White Harbor leaned forward. “The Freys are no better. They speak of wargs and skinchangers and assert that it was Robb Stark who slew my Wendel. The arrogance of it! They do not expect the north to believe their lies, not truly, but they think we must pretend to believe or die. Roose Bolton lies about his part in the Red Wedding, and his bastard lies about the fall of Winterfell. And yet so long as they held Wylis I had no choice but to eat all this excrement and praise the taste.”
(Davos IV, ADwD)

The Freys bear most of the blame for the violation of guest's rights. However, Wyman Manderly is certain of Roose's responsability, as we just saw.

It is certainly known that thousands of northmen were betrayed and murdered at the Twins. Barbrey Dustin said she had spies within Robb's army.
Barrowton sent men with the Young Wolf as well. I gave him as few men as I dared, but I knew that I must needs give him some or risk the wroth of Winterfell. So I had my own eyes and ears in that host. They kept me well informed.
(The Turncloak, ADwD)

We never learned who was Barbrey's spy. It might be Ronnel Stout, apparently a kinsman of Lord Harwood Stout. We never heard news of Ronnel's return to the north, not even when Theon was in Barrowton. In any case, Ronnel Stout did not witness the sending of Ned Stark's bones to Winterfell, since he was with Roose's host at the time, as were all the Barrowton men we heard about.

The hooded man could have reported that the prisoners at the Twins, including the Greatjon, have been sent to the King.
“If you will pardon me for intruding on your grief,” he said, in a dry tone, “we have other matters to consider. When you return to the Twins, please inform Lord Walder that King Tommen requires all the captives you took at the Red Wedding.”
Ser Walder frowned. “These prisoners are valuable, ser.”
“His Grace would not ask for them if they were worthless.”
Frey and Rivers exchanged a look. Edwyn said, “My lord grandfather will expect recompense for these prisoners.”
(Jaime VI, AFfC)
The news of the transfer of the hostages is widely known in the Riverlands.
That same afternoon, the lords of the Trident came to Jaime asking his leave to return to their own lands. He granted it. Lord Piper also wanted to know about his son Marq. “All the captives will be ransomed,” Jaime promised.
(Jaime VII, AFfC)

If the Greatjon is not prisoner at the Twins anymore, both Mors and (especially) Hother have free reign to accomplish vengeance on the Boltons and the Freys, with the caveat that a being a captive of the Crown might not make that much difference ultimately. That fits well with the arrival of Mors under Winterfell's walls simultaneously with the hooded man.

Of course, it is in Barbrey and Roose's interest to keep the news hidden as long as possible, if only to keep Hother Umber loyal to their cause, and distance themselves from the Freys.

The chronology would seem to allow the news to travel. (Jaime freed Wylis Manderly in Harrenhal, then traveled to Darry and then to Riverun, a relatively short journey compared to Wylis Manderly. After Wylis reached White Harbor, at least three months elapsed before the arrival of the hooded man in Winterfell.) A travel by land is less likely, but can't be rule out. However, traveling to Winterfell is difficult given the current weather conditions.

More likely a raven could have reached Mors Umber, who is primarily concerned by the captivity of his nephew and liege lord.

Someone from the south would have brought the news to Mors, it could be a member of the Brotherhood without Banner, since the Brotherhood had spies in Riverun (Tom o' Sevens) and possible friends among the riverlords that could send the raven.

Or Lord Piper, who seems to hate the Freys passionately, could have sent a raven to the Last Hearth (assuming riverlords have birds in their rookery for such a remote destination). Indeed the Pipers have fought with the Umbers under the Stark banner, and they have been betrayed at the Red Wedding. Both families still have hostages at the Twins.

The feelings of Clemence Piper towards the Freys is encapsuled in the following passage, a war council held by Jaime Lannister.
Edwyn bristled. “If my lord of Piper means to imply—”
“I don’t imply, Frey. I say what I mean straight out, like an honest man. But what would you know of the ways of honest men? You’re a treacherous lying weasel, like all your kin. I’d sooner drink a pint of piss than take the word of any Frey.” He leaned across the table. “Where is Marq, answer me that? What have you done with my son? He was a guest at your bloody wedding.”
“And our honored guest he shall remain,” said Edwyn, “until you prove your loyalty to His Grace, King Tommen.”
“Five knights and twenty men-at-arms went with Marq to the Twins,” said Piper. “Are they your guests as well, Frey?”
“Some of the knights, perhaps. The others were served no more than they deserved. You’d do well to guard your traitor’s tongue, Piper, unless you want your heir returned in pieces.”
My father’s councils never went like this, Jaime thought, as Piper came lurching to his feet. “Say that with a sword in your hand, Frey,” the small man snarled. “Or do you only fight with smears of shit?”
Frey’s pinched face went pale. Beside him Walder Rivers rose. “Edwyn is no man of the sword... but I am, Piper. If you have more remarks to make, come outside and make them.”
“This is a war council, not a war,” Jaime reminded them. “Sit down, the both of you.” Neither man moved. “Now!”
Walder Rivers seated himself. Lord Piper was not so easy to cow. He muttered a curse and strode from the tent.
(Jaime VI, AFfC)

We already saw that Jaime informed Lord Piper of the royal order to transfer the hostages away from the Twins. Would Piper conceive the idea of informing the Umbers of the transfer?

But Barbrey Dustin mentions explicitly the Greatjon during the conversation: If you did not hold the Greatjon, he would pull out your entrails and make you eat them, as Lady Hornwood ate her fingers. If indeed the Greatjon is no more at the Twins, then Barbrey is hiding the news from the Freys. So Aenys Frey didn't hear anything of the hooded man's announcement. The captivity of Greatjon is one of the Freys' major assets in Winterfell, and gives them much of their political weight. But I don't see why Barbrey would threaten the Freys and deceive them at the same time. So, I tend to believe Barbrey is sincere and news about the Greatjon have not reached Winterfell yet.

What else could the hooded man have reported?

There is the possibility of the news of Robb's will, which seems to have named Jon Snow as heir to the crown of the north. In all likehood, the Freys have the document, since they got hold of the crown. But Maege Mormont and Galbart Glover were witnesses to the decree. They might have reappeared in the meantime and have contacted Robett Glover.

If the news of the will reached Roose Bolton, and later Ramsay, that might change the political situation. The legitimacy of Ramsay over Winterfell is threatened (which could explain the personal tone of the letter sent to the Wall). There is a possibillity that the northern houses that witness the will would rally around Jon Snow. The Freys could play a role in this, since it is likely that they have the document. Could Barbrey Dustin's use of the term bastard (refering to Ramsay), disparraging thus implicitly all bastards, be an indirect reference to Jon? Except for this detail, I find no trace of the reappearance of the will in the conversation in the solar.

An intriguing possibility would be the news of the survival of the Stark children, which would be embarrassing for Roose just before the battle, and would leave Ramsay useless for his father. The survival was known to Manderly and Robett Glover. But there isn't much in the conversation in the solar that would let us believe that such news reached Roose. If it were the case, we could suppose Theon would be questioned – unless Roose considers Theon to be so much Ramsay's creature that questioning would be useless. However, Ramsay had told Roose that the Stark boys have escaped, so Roose would have little to learn from Theon, and nothing new since Roose has had Theon at his disposal for months. The hooded man could have come with the news that Bran and Rickon hid in the crypts, with a potential proof: the disappearance of the swords. ("Go and see the tombs with your own eyes if you don't believe me".) Or course that would make Barbrey blemish, hence her pale face, since she had seen the disappearance of the swords.

The announce of the survival of Bran and Rickon had been considered by Manderly.
“Roose Bolton has Lord Eddard’s daughter. To thwart him White Harbor must have Ned’s son ... and the direwolf. The wolf will prove the boy is who we say he is, should the Dreadfort attempt to deny him. That is my price, Lord Davos. Smuggle me back my liege lord, and I will take Stannis Baratheon as my king.”
(Davos IV, ADwD)
And by Roose and Ramsay.
“There are times you make me wonder if you truly are my seed. My fore-bears were many things, but never fools. No, be quiet now, I have heard enough. We appear strong for the moment, yes. We have powerful friends in the Lannisters and Freys, and the grudging support of much of the north ... but what do you imagine is going to happen when one of Ned Stark’s sons turns up?”
Ned Stark’s sons are all dead, Reek thought. Robb was murdered at the Twins, and Bran and Rickon ... we dipped the heads in tar ... His own head was pounding. He did not want to think about anything that had happened before he knew his name. There were things too hurtful to remember, thoughts almost as painful as Ramsay’s flaying knife ...
“Stark’s little wolflings are dead,” said Ramsay, sloshing some more ale into his cup, “and they’ll stay dead. Let them show their ugly faces, and my girls will rip those wolves of theirs to pieces. The sooner they turn up, the sooner I kill them again.”
The elder Bolton sighed. “Again? Surely you misspeak. You never slew Lord Eddard’s sons, those two sweet boys we loved so well. That was Theon Turncloak’s work, remember? How many of our grudging friends do you imagine we’d retain if the truth were known? Only Lady Barbrey, whom you would turn into a pair of boots ... inferior boots. Human skin is not as tough as cowhide and will not wear as well. By the king’s decree you are now a Bolton. Try and act like one. Tales are told of you, Ramsay. I hear them everywhere. People fear you.”
(Reek III, ADwD)

That would suppose that the conspirators outside of Winterfell knew about the disappearance of the swords. It doesn't seem that Wex could have told Glover. But Osha left Winterfell with Ned Stark's sword, which bears the mark of Mikken.
Osha carried her long oaken spear in one hand and the torch in the other. A naked sword hung down her back, one of the last to bear Mikken’s mark. He had forged it for Lord Eddard’s tomb, to keep his ghost at rest.
(Bran VII, ACoK)

As it happens, Mikken is mentioned by Crowfood when "Arya" is questioned after the escape. Recall that, according to this analysis, Crowfood and the hooded man were in contact before the man entered the castle. Crowfood even goes out of his way to praise Mikken's steel.
Crowfood had fingered his beard. "Dead now, I suppose. That smith of yours as well. A man who knew his steel. What was his name?"
Jeyne had hesitated. Mikken, Theon thought. His name was Mikken. The castle blacksmith had never made any lemoncakes for Sansa, which made him far less important than the castle cook in the sweet little world she had shared with her friend Jeyne Poole. Remember, damn you. Your father was the steward, he had charge of the whole household. The smith's name was Mikken, Mikken, Mikken. I had him put to death before me!
"Mikken," Jeyne said. 
Mors Umber had grunted. "Aye."
(Theon, TWoW)

An hint to keep in mind at any rate, especially since the other man mentioned by Crowfood, Gage, had been Osha's lover when Theon took Winterfell. Moreover, Crowfood could have named any member of the Stark household that left for King's Landing but he named Mikken and Gage, who are closely related to Osha. (Crowfood last visited Winterfell for the Harvest Feast, when that part of the household had already left, which might have influence his choice in the remaining members.) Of course, Osha herself has never seen Arya.

So has Mors Umber recovered Osha, and perhaps Rickon? The timeline doesn't preclude it, since Davos has left White Harbor at least four months ago. Did the hooded man announce the presence of Rickon?

However, the reappearance of the Stark children has no bearing with the Freys, and would not explain Barbrey Dustin's sudden hostility, unless Barbrey wants to deflect the attention of the northmen on the Freys. Since some funny business happened around the crypts during the last few days in Winterfell: Abel seems to have paid a visit there and Little Walder's body has been found near the entrance.

Did Little Walder lead Ramsay to the crypts to inspect the missing swords?

5. The Escape

One wonder what the hooded man did in Winterfell beside delivering a message to Barbrey Dustin and Roose Bolton. After getting in the Great Hall the hooded man probably went to see Lord Bolton. But then? He might have communicated with Abel and Manderly during the meeting in the solar, supposing Roose left him free reign, which is not particularly likely.

If the hooded man came to coordinate the escape, there could have been an agreement between Abel and Mors that the arrival of the hooded man would signal the presence of Mors Umber outside the castle. That way no message from the hooded man to anyone was necessary, only his presence. However, to coordinate the escape, Abel, Rowan and co needed to send a message outside, simply to warn that the plan of escape would include Theon. They didn't know until a few days before that they would use Theon to exfiltrate "Arya". But the hooded man did more than appear before Abel, since he appears responsible of the circulation of the word kinslayer from Crowfood to Rowan.

There might be a need to exfiltrate Theon from the point of view of the northmen. Indeed Robett Glover's children are prisoner at Harlaw, and Lord Harlaw hosts his sister, Theon's mother. Hence, Theon could prove precious for an hostage exchange – that might even save him during the battle with Stannis. That makes another argument for Robett Glover's involvement in the escape.

We have examined already the possibilities for Abel and the washerwomen to send a message outside: music, snowmen, a Ryswell defector, Squirrel or Abel scaling the Wall.

We saw that the sounding of drums below the Hunter's Gate was synchronized with the sounding of the horn heard at the hour of the wolf.

So the logic of the coordination could have been the following. The hooded man shows up in the Great Hall, which warns Abel and co that Mors is ready outside. Note that Abel was in the Great Hall at the arrival of the hooded man. Then a message is sent back (Squirrel scaling the Wall during the night would be a reasonable explanation), warning that the escape would happen as soon as armies (perhaps specifically the Freys) depart the castle.

What could have happened to the hooded man after going to the Great Hall? It seems clear that if his visit had any importance it remained discreet. If he asked for a private meeting with Roose, it is likely that whatever conversation took place happened in Roose's solar.

If the man remained as Roose's guest, we didn't see him the next morning in the Great Hall. He might have been eliminated by Roose's decision. There is no indication of how he could have left the castle.

The hooded man

6. The devoted squire

Before we turn again to the murder of Little Walder, it might be worthwile to reflect on the Knight of the Laughing Tree's lesson.
When his fallen foes sought to ransom horse and armor, the Knight of the Laughing Tree spoke in a booming voice through his helm, saying, ‘Teach your squire honor, that shall be ransom enough.’
(Bran II, ASoS)
Teach your squire honor...

From the point of view of the institution of knighthood, the tradition of squiring is essential. Indeed, most knights have served another knight during their formative years. Thus, the values and codes and customs are transmitted from generation to generation.

Indeed, squires acquire an intimate knowledge of their mentors: they assist them in everyday life, fill their cups during feasts, tend their horses, take care of their weapons and armor etc. So they are well placed to make a moral evaluation of the man who will lead them to knighthood. From the point of view of the knight, being observed all the time is not without consequences. (Superego in Freudian terms?) So the relation to the squire can be seen as a sort of barometer of the moral value of the knight.

Even not truly knighted characters such as Theon, Brienne and Ramsay do have squires. Let's have a brief look at them by this standard.

It is interesting that Theon has been indifferent to his squire. Wex is a smart boy, and Theon could have benefited by listening to him, if only the boy had been able to speak. Wex' disability seems to reflect Theon's mute conscience while he was ruling Winterfell. Eventually, Wex would turn out to be the one to reveal the truth about what happened in Winterfell. His acquisition of literacy mirrors Theon's progressive coming to terms with his crimes, and could go along a certain amount of redemption.

Brienne was prepared to let herself be hanged to retain her integrity, but she eventually sacrificed her highest personal value to save her innocent squire, Podrick, from an undeserved execution.
Brienne felt the hemp constricting, digging into her skin, jerking her chin upward. Ser Hyle was cursing them eloquently, but not the boy. Podrick never lifted his eyes, not even when his feet were jerked up off the ground. If this is another dream, it is time for me to awaken. If this is real, it is time for me to die. All she could see was Podrick, the noose around his thin neck, his legs twitching. Her mouth opened. Pod was kicking, choking, dying. Brienne sucked the air in desperately, even as the rope was strangling her. Nothing had ever hurt so much.
She screamed a word.
(Brienne VIII, AFfC)

 At the opposite end of the moral scale we are considering, we find Ramsay. He has made of Little Walder a miniature version of himself. And he seems to have eventually murdered him.  Has ever a squiring experience been so disgraceful?

Let's review again Little Walder's life as Ramsay's squire. At the Dreadfort, the behaviors of the Walders seemed indistinguishable.
He remembered the boys as well. They were clad in matching lambs-wool doublets, silver-grey with dark blue trim. Both were squires, both were eight, and both were Walder Frey. Big Walder and Little Walder, yes. Only the big one was Little and the little one was Big, which amused the boys and confused the rest of the world. “I know you,” he whispered, through cracked lips. “I know your names.”
“You’re to come with us,” said Little Walder. “His lordship has need of you,” said Big Walder.
(Reek I, ADwD)
We see them again in Moat Cailin, without any marked difference.
They were just outside the camp when the baying of a pack of hounds told of Lord Ramsay’s approach. Whoresbane was with him, along with half a dozen of his favorites, Skinner and Sour Alyn and Damon Dance-for-Me, and the Walders Big and Little too.
(Reek II, ADwD)
Little Walder seems favored by the Frey family, as Rhaegar Frey says at the Merman's court.
“Lady Wylla,” he said to the girl with the green braid, “loyalty is a virtue. I hope you will be as loyal to Little Walder when you are joined in wedlock.”
(Davos III, ADwD)

There does not seem any such marriage plan for Big Walder. Both Walders are reunited with their kin at Moat Cailin. But Little Walder has closer kin in his sister Walda, and the full brother of this father Hosteen. Big Walder's important close kin, Lothar the Steward at the Twins, has remainded in the shadows. We have seen already the tension between Ramsay and the Freys about the inheritance of the Dreadfort. Obviously Little Walder is caught in between. It must have been tempting for Walda to use Little Walder to spy on Ramsay.

As it happens, a difference seems to appear in the behaviors of the Walders at this point. We see them again in Barrowton. It seems that Little Walder is getting closer to Ramsay.
Little Walder had become Lord Ramsay’s best boy and grew more like him every day, but the smaller Frey was made of different stuff and seldom took part in his cousin’s games and cruelties.
(Reek III, ADwD)

So is Little Walder being influenced by Ramsay, or has he been pushed to get close to Ramsay? In particular, Little Walder is honored by Ramsay.
It fell to Little Walder to keep Lord Ramsay’s cup filled, whilst Big Walder poured for the others at the high table.
(Reek III, ADwD)

Then in Winterfell, we never see Little Walder in the proximity of Ramsay. In particular, he never seems given the role to fill Ramsay's cup. Ramsay does fill a cup of wine himself, during the bedding scene (of course, the importance of the scene has to be relativised, since it might not be the squire's role to be present during the bedding).
Lord Ramsay poured himself a cup of wine.
(The Prince of Winterfell, ADwD)

In Winterfell, Little Walder's main occupation seems to have consisted in the building snowmen. (We see him once dancing with a washerwoman, and he seems to have played dice the night he died.) We never see him with Ramsay.

Has Ramsay relieved Little Walder of his duties because he came to mistrust his squire?

7. Ramsay's Day before the Escape

Now a recapitulation of the last twenty four hours that preceded the escape from Ramsay's point of view.

Let's start with Yellow Dick's death.
This one could not be waved away as some drunken tumble or the kick of a horse. The dead man was one of Ramsay’s favorites, the squat, scrofulous, ill-favored man-at-arms called Yellow Dick. Whether his dick had actually been yellow was hard to determine, as someone had sliced it off and stuffed it into his mouth so forcefully they had broken three of his teeth. When the cooks found him outside the kitchens, buried up to his neck in a snowdrift, both dick and man were blue from cold. “Burn the body,” Roose Bolton ordered, “and see that you do not speak of this. I’ll not have this tale spread.”
The tale spread nonetheless. By midday most of Winterfell had heard, many from the lips of Ramsay Bolton, whose “boy” Yellow Dick had been. “When we find the man who did this,” Lord Ramsay promised, “I will flay the skin off him, cook it crisp as crackling, and make him eat it, every bite.” Word went out that the killer’s name would be worth a golden dragon.
(A Ghost in Winterfell, ADwD)

Note that Ramsay disobeys his father. Of course, he is furious, and might suspect his enemies in the castle: Barbrey Dustin or the Freys. At dinner, Ramsay is not present in the Great Hall, at least until Theon left the hall. Indeed, Theon is bullied by the Bastard's Boys, who speak in their master's name.

After some time of wandering in the castle, Theon is summoned by Roose to Ned Stark's solar.
Steelshanks led him back to the Great Keep and the solar that had once been Eddard Stark’s. Lord Bolton was not alone. Lady Dustin sat with him, pale-faced and severe; an iron horsehead brooch clasped Roger Ryswell’s cloak; Aenys Frey stood near the fire, pinched cheeks flushed with cold.
(A Ghost in Winterfell, ADwD)

Ramsay's absence in the little council is not surprising. Ramsay was a pariah in Barrowton, not admitted to Barrow Hall by Lady Dustin, sent to search for the Freys.
“Barrow Hall and its kitchens are not mine to dispose of,” his father said mildly. “I am only a guest there. The castle and the town belong to Lady Dustin, and she cannot abide you.”
(Reek III, ADwD)
After announcing the coming of Stannis to the assistance, Roose calls a council in Ramsay's absence.
“The hall is not the place for such discussions, my lords. Let us adjourn to the solar whilst my son consummates his marriage. The rest of you, remain and enjoy the food and drink.”
(The Prince of Winterfell, ADwD)

As we just saw, Ramsay has disobeyed his father by divulging Yellow Dick's assassination. So Ramsay is not part of Roose's councils.

It's worth noting that Barbrey seems displeased with Ramsay during the meeting in the solar. We already knew that she can't abide him. But she pointed to Ramsay's cruelty out of context in the conversation.

Later when, when Theon heard the horn in the night, at the hour of the wolf (that is when the night is darkest before the first signs of dawn), there is no sign of Ramsay. However Theon is on the battlements, who knows what happens elsewhere in the castle.

We do not see Ramsay before breakfast on the morning.
Lord Ramsay soon appeared as well, buckling on his sword belt as he made his way to the front of the hall. His mood is foul this morning. Theon could tell. The drums kept him awake all night, he guessed, or someone has displeased him. One wrong word, an ill-considered look, an ill-timed laugh, any of them could provoke his lordship’s wroth and cost a man a strip of skin. Please, m’lord, don’t look this way. One glance would be all it would take for Ramsay to know everything. He’ll see it written on my face. He’ll know. He always knows.
(Theon, ADwD)

Once again Ramsay came with a sword in the Great Hall, which has been prohibited by Roose. Why is Ramsay in a bad mood? Probably for the same reason he argued with his father a moment later.
Up on the dais, Ramsay was arguing with his father. They were too far away for Theon to make out any of the words, but the fear on Fat Walda’s round pink face spoke volumes. He did hear Wyman Manderly calling for more sausages and Roger Ryswell’s laughter at some jape from one-armed Harwood Stout.
(Theon, ADwD)

If Theon is too far away to hear, one wonders about the other lords on the dais (Hother Umber, Aenys Frey, Roger Ryswell, Ondrew Locke, Harwood Stout, but not Barbrey Dustin, Hosteen Frey, the Walders). Is the subject of the dispute private?

After Little Walder's body is brought to the great hall, Ramsay is quick to ask questions, and perhaps intimidate, Big Walder.
Lord Ramsay descended from the dais to the dead boy. His father rose more slowly, pale-eyed, still-faced, solemn. “This was foul work.” For once Roose Bolton’s voice was loud enough to carry. “Where was the body found?”
“Under that ruined keep, my lord,” replied Big Walder. “The one with the old gargoyles.” The boy’s gloves were caked with his cousin’s blood. “I told him not to go out alone, but he said he had to find a man who owed him silver.”
“What man?” Ramsay demanded. “Give me his name. Point him out to me, boy, and I will make you a cloak of his skin.”
“He never said, my lord. Only that he won the coin at dice.” The Frey boy hesitated. “It was some White Harbor men who taught dice. I couldn’t say which ones, but it was them.”
(Theon, ADwD)
A fight erupted then in the great hall between the Freys and the Manderlys. After the carnage.
It took two score Dreadfort spearmen to part the combatants and put an end to the carnage. By that time six White Harbor men and two Freys lay dead upon the floor. A dozen more were wounded and one of the Bastard’s Boys, Luton, was dying noisily, crying for his mother as he tried to shove a fistful of slimy entrails back through a gaping belly wound. Lord Ramsay silenced him, yanking a spear from one of Steelshanks’s men and driving it down through Luton’s chest.
(Theon, ADwD)
Then Roose struggled to pacify the room. But Ramsay threatens Ser Hosteen.
Hosteen Frey’s sword was red almost to the hilt. Blood spatters speckled his cheeks like freckles. He lowered his blade and said, “As my lord commands. But after I deliver you the head of Stannis Baratheon, I mean to finish hacking off Lord Lard’s.”
Four White Harbor knights had formed a ring around Lord Wyman, as Maester Medrick labored over him to staunch his bleeding. “First you must needs come through us, ser,” said the eldest of them, a hard-faced greybeard whose bloodstained surcoat showed three silvery mermaids upon a violet field.
“Gladly. One at a time or all at once, it makes no matter.”
“Enough,” roared Lord Ramsay, brandishing his bloody spear. “Another threat, and I’ll gut you all myself. My lord father has spoken! Save your wroth for the pretender Stannis.”
Roose Bolton gave an approving nod. “As he says. There will be time enough to fight each other once we are done with Stannis.”
(Theon, ADwD)
Finally, Ramsay and his father seem in agreement.

The visit of Theon and the washerwomen in Ramsay's bedroom tell us more. First we have the entrance to the Great Keep.
Half a dozen seasoned Dreadfort men guarded the doors of the Great Keep. “Another bloody bath?” said their serjeant when he saw the pails of steaming water. He had his hands tucked up into his armpits against the cold. “She had a bath last night. How dirty can one woman get in her own bed?”
(Theon, ADwD)
That means that Ramsay was with «Arya» the night before. But Theon wasn't there to bring the hot water etc.
Lady Arya was not there to share the merriment. She had not been seen outside her chambers since her wedding night. Sour Alyn had been saying that Ramsay kept his bride naked and chained to a bedpost, but Theon knew that was only talk. There were no chains, at least none that men could see. Just a pair of guards outside the bedchamber, to keep the girl from wandering. And she is only naked when she bathes.
That she did most every night, though. Lord Ramsay wanted his wife clean. “She has no handmaids, poor thing,” he had said to Theon. “That leaves you, Reek. Should I put you in a dress?” He laughed. “Perhaps if you beg it of me. Just now, it will suffice for you to be her bath maid. I won’t have her smelling like you.” So whenever Ramsay had an itch to bed his wife, it fell to Theon to borrow some servingwomen from Lady Walda or Lady Dustin and fetch hot water from the kitchens. Though Arya never spoke to any of them, they could not fail to see her bruises.
(The Turncloak, ADwD)

So it is not clear who brought the servingwomen. Was Little Walder in charge of the task? Here is the description of the room.
No day had dawned inside this room. Shadows covered all. One last log crackled feebly amongst the dying embers in the hearth, and a candle flickered on the table beside a rumpled, empty bed. The girl is gone, Theon thought. She has thrown herself out a window in despair. But the windows here were shuttered against the storm, sealed up by crusts of blown snow and frost.
(Theon, ADwD)

The closed shutters, the burning candle and the rumpled bed all suggest that Ramsay got up during the night and not in the morning. The fact that the shutters are closed in not to be explained by the cold, since Theon seems surprised that the room is dark. No day had dawned inside this room. It's likely that Ramsay has been waken by the horn at the hour of the wolf and that he left his room, but did not return before breakfast. We know that the breakfast happened during daytime since.
Day stole upon them just as Stannis had: unseen.
Winterfell had been awake for hours, its battlements and towers crammed with men in wool and mail and leather awaiting an attack that never came. By the time the sky began to lighten the sound of drums had faded away, though warhorns were heard thrice more, each time a little closer. And still the snow fell.
(Theon, ADwD)
Another anomaly:
Then he saw her. She was huddled in the darkest corner of the bed-chamber, on the floor, curled up in a ball beneath a pile of wolfskins. Theon might never have spotted her but for the way she trembled. Jeyne had pulled the furs up over herself to hide. From us? Or was she expecting her lord husband? The thought that Ramsay might be coming made him want to scream. “My lady.” Theon could not bring himself to call her Arya and dare not call her Jeyne. “No need to hide. These are friends.”
(Theon, ADwD)

It is not habitual for «Arya» to hide under the wolfskins, since Theon is surprised to see her there. And we have been told that she is naked only when she bathes. So something a bit unusual happened the night before. Was Ramsay even more abusive than usual then?

One more little curiosity. Squirrel needs to find new clothes after giving her own to «Arya».
Squirrel had stripped down to her smallclothes, and was rooting through a carved cedar chest in search of something warmer. In the end she settled for one of Lord Ramsay’s quilted doublets and a well-worn pair of breeches that flapped about her legs like a ship’s sails in a storm.
(Theon, ADwD)

So it seems «Arya» has no more clothes in the bedroom, otherwise why would Squirrel opt for Ramsay's oversized clothes?

Here is a summary of Ramsay's whereabouts during the last day. He wasn't present in the Great Hall at dinner time. He seems to have bedded his wife, since she had a bath the night before, unless the bath was part of a routine. He got up before sunrise, probably woken by the horn. He did not return to his bedroom afterwards. Several hours separated the hornblowing from his entrance in the Great Hall.

There are two periods of time when questions can be asked about Ramsay: at dinner time, including at he time of Theon's encounter with the hooded man, and in the early morning, between the sound of the horn and Ramsay's entrance in the Great Hall.

It seems to me that Little Walder has been murdered the night before. His body has been left in the crypt. It might have been put out by Abel and the washerwomen. In the morning, Big Walder found the body and it was reported to Ramsay. Ramsay is furious to have learnt that Rickon is alive.

8. What has happened?

The chain of events that led to the escape seems to have been started by the hooded man. After the first four murders, and the collapse of the stables, here is an approximation of what has happened.

We start the night before the escape.

Ramsay is not present in the Great Hall for dinner. At that moment Barbrey Dustin is in a good mood. The northmen and the Freys sing together.

The hooded man entered into the hall, probably put his cloak on a peg. Somehow he talked to Roose Bolton, perhaps to Manderly. He brought the news that Theon is a kinslayer, a news that would reach Rowan later. The man is connected to Mors Umber, knows Theon, has learned the truth about what happened when Theon ruled Winterfell from Wex and Robett Glover. He is audacious enough to enter a hostile castle. He is important enough to be heard by Roose Bolton. Robett Glover seems to fit.

Little Walder went out to meet a dice player (Luton or Skinner).

"Arya" took a bath, a sign that Ramsay was with her. Something unusual might have happened in the bedroom that night and  "Arya" seems to have lost all her clothes. Ramsay seems to have suspected her of plotting to escape.

Later, Theon was summoned to the solar, where there is Barbrey, Roose, Roger Ryswell, Aenys Frey. Barbrey pale-faced and severe, warns the Freys. Barbrey has been disturbed by something, probably some news brought by the hooded man. The most likely news is that the hooded man reported that Rickon has been found alive, with the disappearance of Ned Stark's sword as proof. That could have enticed Ramsay to visit the crypt, led there by Little Walder. In any case, Little Walder's body has been moved before it has been found under the snowbank.

The horn has been sounded at the hour of the wolf. Inside the castle, possibly in the burned tower, or perhaps in the crypts.

Then Theon has been delivered to Abel in the burned tower.

Ramsay has been awaken by the horn. The role of Big Walder is unclear. Perhaps he moved Little Walder's body after the murder. Ramsay entered the Great Hall much later in the morning knowing that Little Walder's body has been found. With Big Walder's help, he managed to put the blame on Manderly. Roose was all too happy to send all parties to deliver battle.

To conclude, it is not clear why Big Walder has blood on his hands, what did he hooded man become afterwards, what did he do in Winterfell, how he managed to talk to Roose and to pass a message to Rowan.

The Winterfell Huis Clos