My route to VT takes me along Rt. 12 from MA to Rt. 91 (or 5) in VT. In Walpole, I noticed a sign for homemade donuts last year and made sure to get back to Homestead Farms this year for those amazing donuts. They are seriously worth the drive themselves, fresh out of the vat, freshly frosted with maple (yay!) or chocolate, also sugar or plain. Really really good. I think it's $4.25 for half a dozen non plain donuts. They also sell mums for $5.99 and I'm sure there's some good produce but it's all about donuts for me.
More toward Mass (I think Westmoreland) is the little Pit Stop BBQ shack across from the antiques store. I stopped in to quickly grab something so just got a pulled pork with no sides, it was pretty darn tasty and would have been a bargain if I had the two sides with it at $7.99. Fries looked like hand cut, large portions, definitely worth a stop.