Seige of the deepwood rather than Dreadfort ?

[MizasterJ]

Why would Stannis agree to go after Deep Wood Motte and the Ironmen instead of going after his true enemy of the Bolton's at the Dreadfort?

In Jon chapter 4..Stannis seemed heel bent on claiming the north, which meant over taking the Boltons. Why would Stannis change his mind even with opportunity to take over a mere 50 men at the dreadfort?

I understand that Jon Snow convinced him, but how? Stannis would have had the support of the Umbers. Also if Stannis meant to move quick I dont see how going to Deepwood Motte would be faster, in fact im pretty sure it would be slower, even though they wouldnt be seen.

At this point in the story im unclear if Theon already took control of Moat Cailin for Bolton, but I don't think that would be much of a factor in Stannis's pursuit of the Dreadfort.

They feared Roose Bolton combinging his forces with Ramsay's but was Roose even anywhere nearby ?

[Knight errant]

Because it wins over the support of the Northern people and the dreadfort is such a heavily defended Fortress Jon knew it wouldn't go well. It's a PR coup if Stannis takes over the Boltons ancestral seat but he'd gain more support if he is seen helping the Northerners against the ironborn, he could also enlist the aid of the 3k + Mountain clansmen loyal to House Stark. It's a better plan and detour tbh than attacking the dreadfort. Especially as the Dreadfort attack would have been a trap.

[Lion of Judah]

He kills 2 birds with one stone so to say, win over the Northmen and recapture Winterfell.

[Meddler]

It's actually not that much further, as the crow flies. It is a more difficult trek through the mountains, and thus would take longer, but that's a double edged sword--it would also be much more difficult for Roose and Ramsay Bolton's far superior host to cut Stannis off from retreat after the Northerners retook Moat Cailin, which was considered an inevitability at this point. It also that also meant dealing with the mountain clans as opposed to the Umbers, the former of whom could be won to Stannis's cause, while the latter of whom who were of uncertain loyalty as the Freys still held the Greatjon hostage. It would have been impractical for Stannis to march through the mountains to win the support of the clans and THEN to the Dreadfort--by this point, Roose and Ramsay would have had ample time to join forces, if not flat out beat them in a footrace to the Dreadfort. He might as well retake Deepwood at this point anyway, almost certainly gaining him some Glover support eventually.

So Stannis could either march directly on the Dreadfort, take it, and wait to be and be vastly outnumbered, under siege, and cut off from retreat to the Wall once the combined Bolton host reached them; he could win the mountain clans and march on a Bolton occupied Dreadfort to begin a siege of a well-manned, heavily fortified stronghold; or he could instead go to the lightly held, difficult to defend Deepwood, liberate it from the Ironborn, and attempt to win more of the North to his cause, and at least the formidable House Glover, before deciding his next move. If enough of the North came over to him, he could still march on the Dreadfort, with a much stronger host, or he could retreat to the Wall and regroup, leaving a Flint or a Norrey or some other clansman to hold Deepwood until a Glover could join him and retake it.

[Longspear Ryk]

stannis would have never been able to take the Dreadfort, this was before he has the forces he does now sitting outside WInterfell...

The Dreadfort with my guess is probably the second most defendable castle in the north besides Winterfell...

But listening to Jon Snow he gained the Mountain Clans, A Mormont, an Umber, Glover, andd a Greyjoy...

[Septon Meribald]

Stannis didn't go, because Jon convinced him it was a trap. The King in the North once took two years to starve out Dreadfort during a Bolton rebellion, which Stannis doesn't have the time to do. That would mean assaulting the castle. Even a lightly held Dreadfort, assuming Jon was wrong, would have cost Stannis hundreds of men. Stannis doesn't have hundreds of men to spare, considering that taking the Dreadfort wouldn't necessarily bring anyone new to his cause. So he'd simply be depleted and still have the full host of the Boltons to deal with. Taking Deepwood from the Ironmen, is a gesture of goodwill to the Northmen, which as we see helps bring more of them to his side and costs considerably less than taking the Dreadfort. And of course Jon was right and the Dreadfort was a trap set by Roose, where Stannis was likely to be wiped out completely.

[ab aeterno]

I think the answer is, quite simply, that Stannis isn't a moron. Stannis understands that even though he is a boy, Jon knows the castles and people of the North better than Stannis does. He also understands siege craft because he is an accomplished commander. He is also low on troops. When you are told by someone who should know a) The castle you are going after is going to take far too long to capture; b ) that it might well be a trap, and c) that you can bring the local population on-side and boost your numbers by going a different way, you would be sensible to listen.