I am not sure of the route that you are taking. I would guess the NYS Thruway to the Mass Pike, but that will take you considerably south of Vermont. Of course, you could branch off and go to Bennington. I like Bennington, but it is not really what I would call picturesque. The Four Chimney's Inn is very nice.
Arlington is a bit north of Bennington and has some nice inns such as the West Mountain Inn. More of a small town while Bennington is a small city.
Dorset VT is a very picturesque town that is a bit north of Bennington, in the southwest corner of the state. Or you might consider Woodstock, in the eastern part of the state. Neither are on a direct line from Buffalo to the Cape, but I am assuming that you'd like to meander around a bit and see something besides the interstate. Neither would be that out of the way. (For a picturesque New England Village that's directly en route, you should look into towns in the Berkshires in Massachusetts.)
It really depends a lot on how much time you have to spend on the stop-over. As the poster above says a town in the Berkshires makes sense. Stockbridge is lovely. One of the nicest towns in the area and just off the Mass Pike. There is an exit at West Stockbridge.
Excellent tips, thank you very much!
Very helpful information, as we don't mean necessarily in VT, but rather safe, pretty, and not too far from the route.
From Niagara Falls you could take the thruway (I90) to exit 24 in Albany then I87N, exit 7 to NY7 east, which turns into VT9. That's not too far off the route (adds about 1h15m according to gMaps), puts you through Bennington, Wilmington, and Brattleboro From Brattleboro you'd work your way down to MA2 and take that most of the way into Boston. For a combination of time/off-the-beaten path it's not too bad of a route. You could also cut across the southern part of NH, adds some more time, though.
If could head further north, you start adding more time to the trip but get some more options.
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