Sightseeing
The Tubs
Hopkins Memorial Forest
Northwest Hill RoadLovely hikes. Varied lengths. Great for families.
Prospect Mountain Ski Area
204 Prospect Access RdWonderful Nordic skiing
Sweet trail loop located at historic Park McCullough House.
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The Mile-Around Woods
Woods LaneSweet trail loop located at historic Park McCullough House.
Bennington Battle Monument
15 Monument CirHistory, monument, view
Old Bennington
Beautiful homes, Old Bennington Church, where Robert Frost is buried.
Parks & Nature
hiking, wildlife
Mount Greylock
Highest point in MA. Beautiful hiking trails, amazing view.
Arts & Culture
World class museum
MASS MoCA
1040 Mass MoCA WayUnbelievable. World class museum 25 mins form Mason Hill.
The Clark Art Institute
225 South StBennington Museum
75 Main StRobert Frost's Shaftsbury residence. Museum shop and walking trail.
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Robert Frost Stone House Museum at Bennington College
121 Vermont Rte 7aRobert Frost's Shaftsbury residence. Museum shop and walking trail.
Essentials
Bennington
Food Scene
can't miss. amazing bakery!
Allegro
520 Main StDrinks & Nightlife
Cool little bar with live music on weekends. Kambucha on tap.
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Harvest Brewing
201 South StCool little bar with live music on weekends. Kambucha on tap.