Sightseeing
Towering above the town of Bennington at 306 feet and 4 and ½ inches tall, the Bennington Battle Monument is the tallest building in Vermont and the third-tallest battle monument in the world. It commemorates the famous Battle of Bennington, fought in nearby Walloomsac, New York in 1777.
72 locals recommend
Bennington Battle Monument
15 Monument CirTowering above the town of Bennington at 306 feet and 4 and ½ inches tall, the Bennington Battle Monument is the tallest building in Vermont and the third-tallest battle monument in the world. It commemorates the famous Battle of Bennington, fought in nearby Walloomsac, New York in 1777.
A stop in the Military Gallery will give you an overview of the Battle of Bennington and Bennington’s Revolutionary War history, complete with an exhibit of Vermont-made firearms.
61 locals recommend
Bennington Museum
75 Main StA stop in the Military Gallery will give you an overview of the Battle of Bennington and Bennington’s Revolutionary War history, complete with an exhibit of Vermont-made firearms.
Henry Covered Bridge
475 River RdThe Robert Frost Stone House Museum is a literary landmark located only minutes away from Frost's gravesite in Old Bennington.
32 locals recommend
Robert Frost Stone House Museum at Bennington College
121 Vermont Rte 7aThe Robert Frost Stone House Museum is a literary landmark located only minutes away from Frost's gravesite in Old Bennington.
The house, a 35-room mansion built by skilled artisans over the course of 18 months, is a prime example of Second Empire design, and represents a specific period of architectural history in the United States.
20 locals recommend
Park-McCullough Historic Governor's Mansion
1 Park StThe house, a 35-room mansion built by skilled artisans over the course of 18 months, is a prime example of Second Empire design, and represents a specific period of architectural history in the United States.
Oldcastle Theatre Company is one of the longest running professional theatre companies in America. It is a not-for-profit theatre company devoted to producing high-quality, intimate, professional theatre for audiences across Southern Vermont, the Capital Region, and the Berkshires.
15 locals recommend
Oldcastle Theatre
331 Main StOldcastle Theatre Company is one of the longest running professional theatre companies in America. It is a not-for-profit theatre company devoted to producing high-quality, intimate, professional theatre for audiences across Southern Vermont, the Capital Region, and the Berkshires.
Silk Road Covered Bridge
Silk RoadLocated in Manchester, VT, only a 30 minute drive. Summer home of Abraham Lincoln's eldest son, Robert Todd Lincoln.
158 locals recommend
Hildene, The Lincoln Family Home
1005 Hildene RdLocated in Manchester, VT, only a 30 minute drive. Summer home of Abraham Lincoln's eldest son, Robert Todd Lincoln.
Located in Williamstown, MA, about 30 minutes drive from Bennington. A really great art collection in a college town with good restaurants and shops.
329 locals recommend
The Clark Art Institute
225 South StLocated in Williamstown, MA, about 30 minutes drive from Bennington. A really great art collection in a college town with good restaurants and shops.
A beautiful campus, with 440 acres of sweeping views. Architectural Digest includes Bennington College on its list of the country's "Top 10 Campuses with Best Architecture."
10 locals recommend
Bennington College
1 College DrA beautiful campus, with 440 acres of sweeping views. Architectural Digest includes Bennington College on its list of the country's "Top 10 Campuses with Best Architecture."
MASS MoCA exhibits art by both well-known and emerging artists, focusing on large-scale, immersive installations that would be impossible to realize in conventional museums. The broad-shouldered, raw industrial character of our soaring galleries (with 250,000 square feet of open and often naturally lit space) has proven both inspiring and liberating to artists.
MASS MOCA by Design
50 Spring StreetMASS MoCA exhibits art by both well-known and emerging artists, focusing on large-scale, immersive installations that would be impossible to realize in conventional museums. The broad-shouldered, raw industrial character of our soaring galleries (with 250,000 square feet of open and often naturally lit space) has proven both inspiring and liberating to artists.
Food scene
Elm Street Market
251 Elm StThe Grille
180 Country Club DrAllegro
520 Main StThe Publyk House
782 Harwood Hill RdTHE MILLER'S TOLL DINNER CLUB & LOUNGE
716 Main St421 Craft Bar and Kitchen
421 Main StreetMadison Brewing Company Pub & Restaurant
428 Main StYour Belly's Deli
100 Pleasant StThe Blue Benn
314 North StMan of Kent Tavern
4452 New York 7The Coffee Bar
109 South StreetActivities
Prospect Mountain Ski Area
204 Prospect Access RdStratton Mountain
Mount Snow
Hoosick Falls Country Club
73 Richmond AveMount Anthony Country Club
180 Country Club Dr