Did Ramsay really leave Winterfell and...

[Mithras]

march on Stannis after Theon's escape? Theon assumes that he was coming but why should he?

He had spearwives (and possibly Mance if he was captured) to torture.

The condition of Stannis was reported by the treacherous maester to be terrible. They were said to be freezing and starving. Even the Freys alone should be enough to wipe them out according to the Boltons.

Roose had too many men in a too small space. Both the Manderlys and Freys were people he wanted to get rid of. After the "mayhaps" incident, Roose would not suffer another quarrel like that and he openly said that after Stannis was done, they were free to resume where they had stopped. Roose wants only a single faction (Manderlys or Freys) to return, not two.

Ramsay's bride was missing. He probably thought that Stannis was behind the kidnapping of fArya but the logic says that Stannis would not have them come to crofter's village where they were known to be starving and unable to move. Instead, Stannis would send them to the Wall directly from Winterfell. Knowing that Ramsay is a hunter of women and fArya was of extreme importance to her, he should have gone North along kingsroad and look for trails of his bride and his Reek.

[aryagonnakill#2]

I know its snowing pretty hard, but a horse with a double load is going to leave 1 hell of a footprint, let alone 500 horses. I have to assume they could track the Umbers party.

Time is of the essence with both Jeyne Poole and Theon because Theon can tell people that Bran and Rickon are alive and Jeyne can confess to being Jeyne, and were I Ramsay I wouldn't want Manderly men questioning them on the way back to WF, so I can see a reason for Ramsay going. With the Freys and Manderlys gone I think the Boltons make up the vast majority of the manpower within WF so it stands to reason they could send 1k of the 4 they have to see the battle finished the way they want it finished.

There is also Ramsay's personality to consider. Even if Roose didn't want him to leave Ramsay could easily grab a few hundred men and say come with me.

Then there is Roose to consider. Without Jeyne Poole posing as Arya Ramsay is more of a hindrance than a help. He endangers any heirs from Walda, Roose himself, and angers all of the other Northern lords. I dare say that without Jeyne and Theon, Ramsay give Roose nothing but problems.

We really have no idea, but I have not forgotten that long ago Roose told Arya he assumed Ramsay would kill him 1 day, maybe that day already came.

[Lady Blizzardborn]

No. I don't think Ramsay left Winterfell at all. I'm not even positive the Bastard of Bolton is still alive.

[Minstral]

No. I don't think Ramsay left Winterfell at all. I'm not even positive the Bastard of Bolton is still alive.

But of course hopeful that he is not.

I'm guessing that it is a combination of Theon's dread of Ramsay and that he has gotten an idea of how he would act. As brash and sadistic as Ramsay has shown himself to be he has also shown himself to be a quick thinker on his feet. If he is out on the field then he is likely a wildcard that Stannis, and perhaps Roose, is not taking into consideration.