As classically fall-in-New-England as it gets. Learn about a pivotal event in the American Revolution, visit the gravesite of Robert Frost and walk around the original village of 130 houses all recorded on the National Register of Historic Places.
Cute stores - many of the antique or VT-centric variety - plus good breweries, lunch spots, etc.
The Bennington Area Trail System is amazing and abundant - perfect Saturday morning activity (weather permitting). Visit their website for the full roster.
Manchester, VT is about 30 minutes north of Bennington - a beautiful town to walk around, also an opportunity for some outlet shopping if that’s of interest (Orvis, Marimekko, Theory, Pendleton) and great kitchen store. Head’s up that it’s peak season and crowds will follow.
Williamstown, MA is about 15 minutes southeast of Bennington, another beautiful town to walk around. Should time permit, visit The Clark - great museum and the grounds are so lovely.
On Main St in Bennington. Amazing cocktail list and good food too (think: upscale bar). Their outdoor space is great, overlooks the river.
Cozy Italian food
Classic in-town pizza place with a nice little bar setup inside - and a good VT beer list - plus a fire pit and heaters for outdoor dining.
Very good sandwiches.
Surprisingly good bagels for outside NY
Bennington is home to the Green Mountain Mennonite Fellowship. As merchants, they are among the best when it comes to candy, spices, baked goods, jams, honeys - great sandwiches too.
Good brewery
Another good brewery