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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. Please refer to the websites for current information about hours and admission, including seasonal closures. 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.

Innkeeper’s tip: For an extra dose of adventure, visit during Battle Days for historical reenactments, cannon fire and a downtown parade. Typically the 2nd week in August, check website for details.


Bennington Farmer’s Market

US Route 7-North  Bennington, Vermont

For those of you making a return trip to this delightful market, it is in a new location in front of the deer park at the Vermont Veterans’ Home.  There is plenty of parking. 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 dates and hours.

Discover more with our Four Chimneys Inn blog article: Green Veggies and Good Times at the Bennington Vermont Farmers Market.

Innkeepers Tip: Bring your own shopping bags as you will find many goodies that you will want to bring home!


Bennington Museum

75 Main Street, Bennington, Vermont Phone: 802-447-1571.
A lovely 1/4 mile walk from the inn. 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. Check website for hours and loads of special events and activities.

Innkeeper’s tip: Spend and hour, or spend all day. Either way, plan to visit the museum shop for a wide selection of gifts and one-of-a-kind works from Vermont artisans.  P.S. Don’t forget to save time for the Aiken Wildflower Trail located directly behind the museum.


Clark Art Institute

225 South Street Williamstown, Massachusetts 01267 Phone: 413-458-2303
Approximately 12 miles from The Four Chimneys Inn. A tremendous permanent collection plus special exhibits and programs.  Photo Credit: Tucker Bair

Innkeeper’s tip: Bring your walking shoes to enjoy the gorgeous trails behind the museum. Enjoy lunch on charming Spring Street in Williamstown.

The Dollhouse and Toy Museum of Vermont

212 Union Street Bennington, Vermont
Approximately a 5 minute drive from The Four Chimneys Inn. The museum is open most Saturday, Sunday and holiday afternoons from 1-3:30pm.  This  delightful 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. The perfect afternoon activity for the collector or the child at heart.

Innkeeper’s Tip: This museum is a labor of love of its proprietor. If the hours don’t meet your travel schedule, give a call and more likely than not, they will open just for you by appointment.

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. Goat Farm. Pollinators. Walking trails. Seasonal peony gardens. Cross country skiing and snowshoeing with rentals available.

Innkeeper’s tip: There is no restaurant on site, creates the perfect opportunity to pick up Boars Head sandwiches  at Elm Street Market and enjoy on the beautiful Hildene picnic area.


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.

Innkeeper’s Tip: To get a real feel for the historic church, the family pew boxes, and the welcoming New England congregation, attend Sunday service after a hearty breakfast at the inn.

Park McCullough Mansion Historic Estate an Gardens

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

Innkeeper’s tip: Walk the grounds. Take a bucolic hike in the mile Around Woods, but definitely spring for the house tour! Each time I have been, a delightful docent gave a brief, but interesting tour with tales of the Park family, their role in Bennington and in hosting President Benjamin Harrison.

Robert Frost Stone House Museum

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

In addition to a museum featuring all things Frost, there is a wonderful, well-marked hiking loop to Lake Paran.

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.

Innkeepers Tip:  Don’t miss this! The owner is incredibly friendly and animated with wonderful stories that will delight just as much as these adorable alpacas. Bring your holiday gift list. She has a small shop of alpaca hats, sweaters, scarves and more. Not far from the Mile Around Wood hiking trail and Park McCullough Mansion, so you can tackle all three in one afternoon. Check website for hours.

Historic Deerfield Massachusetts

80 Old Main Street Deerfield, MA Phone: 413-775-7214 Approximately 50 minutes from The Four Chimneys Inn.
Historic Deerfield 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.

Innkeeper’s Tip: Make a day of it. Use the inn as your launchpad. Stop at the Vermont Country Store in Weston, have lunch on the waterfall at Simon Pearce and wander through downtown Woodstock, Vermont.

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.

Discover more with our Four Chimneys Inn blog article: Guide to the best Covered Bridges in Vermont