hmm, welcome to posting on the boards! Don't know if I can be of much help as most of the places I know in that area are open during the day. I'd suggest making a few phone calls to find out how late they might be open.
1.) West Taghkanic Diner in Ancram, NY
Roadfood review - http://www.roadfood.com/R...4/west-taghkanic-diner
I've never been but having been dreaming of it ever since I saw the roast turkey dinner picture in the review. I checked their website and they are open until 11pm on Fridays and 10pm on Saturdays and Sundays. However, as the Roadfood rule goes, CALL AHEAD!! The website may not be accurate, they may close early if business is slow, family commitments, etc... So if you're leaving on Friday, there may be a shot at getting there before 11pm.
I ran a half marathon in Woodstock in June 2011 and lots of great places to eat but they roll up the sidewalks pretty early in that town so I don't think there are any late night options.
Here's a list of VT Roadfood restaurants: http://www.roadfood.com/R...City&ps=1&s=VT
And my Trip Report from my visit to Woodstock last year: http://www.roadfood.com/F...427&mpage=1#656656
If you're in Woodstock for breakfast you could try hitting up the Wasp Snack Bar. Hope you find some tasty vittles on your journey!