Brattleboro seems to be very organically oriented. The farmers market on Sat is very festive, too bad you'll miss it but the Humble Kitchen food truck is parked in Harmony Parking Lot (downtown area) and serves their own version of bahn mi sandwichs and pho. If it's still warm enough to eat outside (they have a couple of tables), it's very good. They have a facebook page.

I'm not familiar with the route. I would be tempted to go a bit out of the way and go up to Nashua and then west on Rt 101 to Keene and then over to Brattleboro. For a unique lunch (reservations absolutely necessary) there's are herbal luncheons at Pickety Place in Mason NH. Rt 101 is a pretty drive. If I didn't go to Pickety Place I would pick someplace in Peterborough NH which has a great little downtown area and a fantastic bookstore (both new and used). Rt 101 will also take you past the offices for Yankee Magazine in Dublin NH.

The apple orchards are at their best right now. I usually recommend Gould Hill in Hopkinton NH for both view and variety of apples but it is very much out of your way. Hope some other poster will point you toward a good farmstand with a good variety of apples. You might want to check out Gould Hill's website just to see what's in season. (Ginger Golds, my favorites, are done but Macoun are available around here right now).

If you like chocolate, a side trip to Burdicks in Walpole NH is a must.

If you like to bake, a trip further north to King Arthur Flour in Norwich VT is a must. Lots of great ingredients.

Thanks for the info dfrostnh. I'll have to map these out. I'm craving apples right now just thinking about getting fresh ones!

Does anyone else have any suggestions? My SO loves, loves, loves ice cream. Any special places we should hit?

You will be near Grafton Vermont, perhaps the most picture perfect little village in the state. For lunch, you can dine at the Grafton Inn's tavern, or pick up a sandwich at the small grocery store and dine on the outdoor picnic tables. Grafton's Rushton Farm supposedly has the best ice cream in Vermont. There is also the Grafton Cheese company and a sugar house.

It would be a pretty good drive on your free day, but you could tour the Ben and Jerry's factory between Montpelier and Burlington: http://www.benjerry.com/scoop-shops/factory-tours/

I'm sure your inn can give you good advice on nearby ice cream shops as well.

I'd never detour for Ben and Jerry's, personally.

I agree, too much of a detour esp during tourist season, for ice cream you can get any place. NH has an ice cream map. I think Kimball Farms has a location near your route (Westford MA is one location).
Here's the link to the NH ice cream dairy trail
http://www.nh.com/dairytrail

Some locations close in October. Also, the goal is to find the places with their own ice cream or at least a great local brand. Indian pudding ice cream is hard to find unless it's local. We didn't see ginger on the list recently but that's another flavor that is sometimes only available in the fall.
Here's the link to Granite State Candy in Concord NH where they make their own ice cream
http://www.nhchocolates.com/theicecreampage/

I've heard that Richardson's supplies some of the small, independent ice cream stands around New England but I don't see it mentioned on their website.
http://www.richardsonsicecream.com/

ps It's too bad you are headed to VT. The Sandwich Creamery in NH is an adventure to find and is located near one of the most beautiful little towns in NH a short drive from Lake Winnipesaukee. Their list of flavors isn't extensive but they supply some other places in NH
http://sandwichcreamery.com/html/about_the_creamery.html

We haven't been to Sandwich in quite some time but we used to visit a couple of times a year and twice saw a black bear near the road. Hopefully you can find a similar kind of place in VT ... farmers making a go of it, diversifying locally, and preserving great foods and flavors.

I would not make a big detour to go to Ben and Jerry's but I know people who aren't from ice cream-centric New England who really enjoy the tour when they are in the area (and ice cream New England people who enjoy it too). I mentioned it because the point was the tour--of course, we all know we can get the ice cream at a number of places. I still think it can be fun if someone is nearby.

If you go to Quechee (and it's worth the trip) go to Frozen Memories Ice Cream. http://www.quecheegorge.com/frozen-memories.php