The Sharon, VT spot is nice but there's also not a lot there. It's best during the winter when they have their Christmas lights up or during the fall due to leaves. You could still make a day trip out of driving up to Ben and Jerry's, then back through Sharon on the way back.

If you want to do some hiking you could go up to New Hampshire and hike Mt Monadnock or go all the way up to the White Mountains.

You might want to go check out one of the coastal towns, even though it will be before their peak season and some stuff will be closed. Newport, RI is an easy day trip - walk along the Cliff Walk and then go in to see the Breakers mansion. Rockport, MA is another good spot - or somewhere down in Cape Cod.

How far have you ventured outside of Boston? You could go to Salem, or go out to Minuteman Park in Lexington/Concord. You could even hit both of those in one day.