Parks & Nature
Activities include boat rental, picnicking, swimming, fishing, hiking. Open Memorial Day to Columbus Day.
15 locals recommend
Woodford State Park
142 State Park RdActivities include boat rental, picnicking, swimming, fishing, hiking. Open Memorial Day to Columbus Day.
Beautiful views of downtown Bennington and surrounding mountains. Particularly beautiful in the fall!!
72 locals recommend
Bennington Battle Monument
15 Monument CirBeautiful views of downtown Bennington and surrounding mountains. Particularly beautiful in the fall!!
Long Trail
Unnamed RoadHead south for Harmon Hill view of Bennington (moderate to difficult)
Great easy hike (about 1.5 miles total) to Mt. Olga Fire Tower (open Memorial Day to Labor Day)
53 locals recommend
Molly Stark State Park
705 VT-9Great easy hike (about 1.5 miles total) to Mt. Olga Fire Tower (open Memorial Day to Labor Day)
Rentals from kayaks and paddle boards to jet skis and power boats.
27 locals recommend
High Country Marine
403 VT-9Rentals from kayaks and paddle boards to jet skis and power boats.
Hamilton Falls Road
Hamilton Falls RoadHike to a waterfall
Valley Trail
Valley TrailMt. Mills West Picnic Area
1 Woods RdSecluded swimming hole
Swimming Area at Harriman Reservoir
Local swimming hole and boat launch
Arts & Culture
Bennington Museum
75 Main StArt and local history
Robert Frost Stone House Museum at Bennington College
121 Vermont Rte 7aSouthern Vermont Natural History Museum
Essentials
Walmart Supercenter
210 Northside DrThe Home Depot
121 N Bennington RdShaw's
97 E Main StW W Building Supply
434 Vermont Route 100closest hardware store
River Valley Market
661 Vermont Rte 100Food Scene
Wahoo's
2 Whites RdGreat outdoor road stand you can bring your dog to. Great food!
Anchor Seafood Restaurant
8 S Main StGood seafood.
Cask & Kiln Kitchen
4 N Main StUpscale dining
The Publyk House
782 Harwood Hill RdGood drinks and food with nice views north of Bennington.
Lumber Jack's Coffee And Snacks
5103 NY-7Awesome maple lattes and great cider donuts.
Beer Naked Brewery
7678 VT-9Specialty pizza and micro brews with a 100 mile view
Pizza joint right around the corner with arcade, bowling alley and mini golf
23 locals recommend
North Star Pizza
179 Vermont Rte 100Pizza joint right around the corner with arcade, bowling alley and mini golf
Tony's Pizza
194 Vermont Rte 100Local pizza
The Vermont Country Deli Market
450 Vermont 9Amazing cheddar maple pulled-pork sandwich
The White House Inn
178 VT-9Upscale dining.
Maple Leaf Tavern
3 N Main StGreat local pub with good burgers
La Casita
14 S Main StGreat Mexican food.
The Village Roost
20 W Main Stlocal coffee shop
Cup N Saucer Restaurant
157 Vermont Rte 100local greasy spoon
Wilmington Roadhouse
4 Old Ark RoadDot's
3 W Main StWilmington institution. Very often a line to get in.
Drinks & Nightlife
Snow Republic Brewery
33 Vermont Rte 100Great micro brew just down the road with a great atmosphere
Awesome pub with decent grub that sits above the Connecticut river in Brattleboro.
114 locals recommend
Whetstone Station Restaurant and Brewery
36 Bridge StAwesome pub with decent grub that sits above the Connecticut river in Brattleboro.
Micro brew with all the sour beers you can possibly imagine.
23 locals recommend
Hermit Thrush Brewery
29 High StMicro brew with all the sour beers you can possibly imagine.
Snow Barn
294 Handle RdGreat night life, particularly during the winter.
Shopping
Flea market and antiques open mid-May to mid-October.
21 locals recommend
Wilmington Antique and Flea Market
236 VT-9Flea market and antiques open mid-May to mid-October.
River Bend Farm Market Wilmington
136 Vermont Rte 100