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.
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, but check website for details.
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!
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.
324 County Street, Bennington, Vermont Phone: 802-205-8033
Approximately 1.75 miles from The Four Chimneys Inn. Bennington Potters is 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. (temporarily closed due to covid, but you can still find all of their beautiful treasures online with pick up in Bennington, or ship to your home.)
Innkeeper’s tip: Start with a piece or two of your favorites and before you know it you will have a gorgeous collection. Bennington Potters has been in business for more than 70 years. Visitors
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. Thai, Indian, pizza, Mediterranean and sandwiches. Save room for the best-ever hard ice cream at Lickety Split!
212 Union Street Bennington, Vermont
Approximately 5 minutes from The Four Chimneys Inn. The museum is open most Saturday, Sunday and holiday afternoons from 1-4pm. 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 it’s 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.
216 West Main Street Bennington, Vermont 3/4 mile from The Four Chimneys Inn.
A mecca for old-car-lovers and their friends. Visit the Old Car Museum (check website for hours) and be sure to check the event calendar for cruise-ins and other activities all summer long.
Innkeeper’s Tip: Mark your calendar for summer cruise-ins (typically on Thursday evenings, but check website for schedule). A festive gathering where old-car-owners can showcase their cars from antique to vintage and old-car-lovers can admire. Popcorn for all!
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: 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.
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.
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.
1 Park Street North Bennington, VT Phone:802-442-5441
Approximately 10 minutes from The Four Chimneys Inn.
Read our latest blog about this historic mansion and event venue.
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.
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
Innkeeper’s tip: Take a slice of Vermont home with you. Tony captures the best of Vermont landscapes and covered bridges.
Robert Frost Grave
At The Old First Church cemetery Old Bennington, Vermont
¼ mile from The Four Chimneys Inn.
Innkeeper’s Tip: The perfect place to stretch your legs upon arrival at the inn.
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.
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.
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.
Innkeepers Tip: For our fly-in guests, if you fly in to Boston, you can stop on your way to Bennington.
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
West Road Manchester, Vermont 05254 Phone: 802-362-1405
Approximately 20 miles from The Four Chimneys Inn.
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.
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