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For those looking for Vermont weekend getaways, the area around our Bennington, VT bed and breakfast has all kinds of great options. Bennington County is as rich in revolutionary war history as it is in natural mountainous beauty. For those travelers who prefer to plan ahead, we hope you will find this list of things to do in Bennington helpful as you plan your vacation. Celebrating an anniversary or birthday? Take a look at our packages and plan the ultimate romantic getaway in New England.

Bennington Battle Monument

15 Monument Circle, Old Bennington, Vermont Phone: 802-447-0550. A short and beautiful walk from The Four Chimneys Inn. Also, the most visited of Southern Vermont Attractions. In fact, the most visited historical site in Vermont.

vermont farmers market with cherries and blackberries

Bennington Farmer’s Market

150 Depot Street Bennington, Vermont Saturdays, 10 am-1 pm A pleasant 1 mile walk from The Four Chimneys Inn. And plenty of parking for those preferring to drive. Please note that from November through April, the Farmer’s Market moves inside at the First Baptist Church at 601 Main Street. Visit website for winter hours.

Bennington Museum

75 Main Street, Bennington, Vermont Phone: 802-447-1571. A lovely 1/4 mile walk from the inn. Summer hours: June 1 through October 30, 10am – 5pm daily. Closed July 4. Winter hours: November, December and February through May open 10 am – 5pm daily, except Wednesdays. Closed for the month of January. The Bennington Museum is known as the trusted caretaker of the largest collection of Grandma Moses art and memorabilia available to the public. Located in the heart of Southern Vermont, the museum’s galleries evoke the rich heritage of this state with collections of paintings to pottery to historical objects and fine furniture.

Bennington Potters

324 County Street, Bennington, Vermont Phone: 802-205-8033 Approximately 1.75 miles from The Four Chimneys Inn. Visit the largest working craft pottery in the U.S. Learn more about pug mills and forming presses, secret clay recipes, ‘slip’, back stamps and ‘burlaping’. Tours offered daily, year round.

Clark Art Institute

225 South Street Williamstown, Massachusetts 01267 Phone: 413-458-2303 Open Tues-Thurs 10am – 5pm. Closed Christmas Day and New Year’s Day. Approximately 12 miles from The Four Chimneys Inn. Photo Credit: Tucker Bair

The Dollhouse and Toy Museum of Vermont

212 Union Street Bennington, Vermont Approximately 5 minutes from The Four Chimneys Inn. The museum is open Saturday, Sunday and holiday afternoons from 1-4pm year round or by appointment. The museum contains a permanent collection of dollhouses, from simple Cape Cod houses to elaborate Victorian houses. In addition to the dollhouses and many dolls, there also are trains and trucks on display as well as educational toys.

Hemmings Motor News Car Lover’s Oasis

216 West Main Street Bennington, Vermont 3/4 mile from The Four Chimneys Inn.

Hildene, The Lincoln Family Home

1005 Hildene Road Manchester, VT Phone:802.362.1788 Approximately 24 miles from The Four Chimneys Inn. Beautiful estate of Robert Todd Lincoln. Self guided tours. A fully restored Pullman car. Cross country skiing and snowshoeing with rentals available.


87 Marshall Street North Adams, Massachusetts 01247 Phone: 413-662-2111 Approximately 16 miles from The Four Chimneys Inn.

Museum of Fly Fishing

Route 7A South Manchester, VT 05254 Phone: 802-362-3300 Approximately 25 minutes from The Four Chimneys Inn. The American Museum of Fly Fishing maintains a program of changing exhibitions in its Leigh H. Perkins Gallery that highlights the fly-fishing artifacts of the famous and not-so-famous.

Old First Church

Rte 9 and Monument Avenue, Old Bennington, Vermont Phone: 802-447-1223 The oldest church in Vermont and a very short walk from the Four Chimneys Inn. The Old First Church is also the grave site of Robert Frost.

Park McCullough House Historic Estate an Gardens

1 Park Street North Bennington, VT Phone:802-442-5441 Approximately 10 minutes from The Four Chimneys Inn.

Paintings in Watercolor

Tony Conner Gallery Viewings and Individual Classes by appointment Bennington, Vermont 05201 Phone: 802-375-5548 Rich New England Landscapes available for purchase. Private or group classes on site with advance reservation. Tony Conner is an award-winning artist whose work is regularly included in national juried exhibits. Photo Credit: Tony Conner

Sign for Robert Frost Grave

Robert Frost Grave

At The Old First Church cemetery Old Bennington, Vermont ¼ mile from The Four Chimneys Inn.

Robert Frost Stone House Museum

Route 7A in nearby Shaftsbury, Vermont About 7 miles from The Four Chimneys Inn.

Shaftsbury Alpacas

12 State Line Road Route 67 on the VT/NY border North Bennington, VT 05257 Approximately 5 miles from The Four Chimneys Inn.

Historic Deerfield Massachusetts

80 Old Main Street Deerfield, MA Phone: 413-775-7214 Approximately 50 minutes from The Four Chimneys Inn. Historic Deerfield is open daily from 9:30-4:30 during the regular reason, and offers guided tours and self-guided tours of the museums, houses, and buildings. Historic Deerfield also offers special events for families, workshops, forums, lectures, and educational programs throughout the year.

Simon Pearce Gallery and Restaurant

Queechee, Vermont Phone:802-295-1470 Approximately 2 hours from The Four Chimneys Inn. Beautiful setting for lunch with views of waterfalls and covered bridge. Watch the glass-blowers in action in their on-site studio. Photo Credit: Simon Pearce

Southern Vermont Arts Center

West Road Manchester, Vermont 05254 Phone: 802-362-1405 Approximately 20 miles from The Four Chimneys Inn.

Tour: Back Road Discovery Tours

Revolutionary and Civil War Tours Daily 9:30 – 11:45 am Southern Vermont Sampler Tour Daily: 1-4 pm Phone: 802-362-4997 Tours originate in Manchester, Vermont Approximately 25 minutes from The Four Chimneys Inn.

cored covered bridge in snow bennington vermont

Vermont Covered Bridges

Bennington County, Vermont There are five covered bridges in Bennington County as well as the Covered bridge museum.