Yeah, all this sounds really good. I'll research more and pare down the route. Thank you!
Just chiming in to second the recommendations for the Quechee/Woodstock area. Quechee has been my second home for about 20 years now, and it's well worth a visit. I'm a little jealous, actually, because being a teacher I almost never have a chance to get up there during the foliage. Simon Pearce has fantastic food as well as the glassware. There's a short trail at the Quechee Gorge that takes you down to the river, and it's a really pretty hike. In Woodstock, right adjacent to town, you can do a quick hike up Mt. Tom for great views.
Down in Windsor, as Albertan Ski Girl mentioned, Ascutney has some great hikes to the summit and if you stop by the base lodge area of the old ski resort while you're there you can see the very cool rope tow that local volunteers built so as to provide free skiing for kids and beginners. I know you're thinking "Why would I go out of my way to see a rope tow?" But it's honestly really impressive, especially considering that it was build solely with donations and volunteer/donated labor.
The Harpoon brewery in Windsor has good food and beer (of course) but beware that they close at around six p.m. which is an insane closing time for a brewery and makes no sense.
Up by Killington, across from the Long Tail Inn, you can do a beautiful 3-mile hike up the AT/LT to the top of Pico Peak for some really spectacular views.
I know you're doing just a quick trip and wouldn't have time for all of this, but I just thought I'd throw out some of my favorites.