WHY GO: The lush, green mountains around Bennington VT, just over the Massachusetts border on Route 7, are the defining aspect of this region – inspiration for poets and artists like Robert Frost, Grandma Moses, and Norman Rockwell. And for entrepreneurs, as well.
Bennington Pottery, Dion Snowshoes (“performance snowshoes”), and Hemmings Motor News all originate in Bennington VT. Discover the appeal of this stunning region on this romantic getaway that includes, of course, great craft beer, awesome cider donuts, and luxury accommodations.
Things To Do In Bennington VT (And Nearby)
GO: Vermont Welcome Center, Bennington
This is that rare State Welcome Center that is not on a major interstate. At the intersection of Routes 7 and 9 – stop here for a fantastic view of the Bennington Monument, free Green Mountain Coffee, and, according to many visitors, the “cleanest public bathrooms anywhere.”
Well-trained, conscientious Vermont “Ambassadors” will guide you to the best places depending on your interests. Open 7-9 daily. Free.
TOUR: Bennington Monument
Standing at 306 ft. 4 ½ “ tall, the limestone Bennington Battle Monument obelisk is the most visited historical attraction in Vermont. It’s also its most visible.
Rising up through the green foliage, it can be spotted from afar. The monument was erected in the 1800’s to commemorate the Revolutionary War Battle of Bennington, fought on August 16, 1777.
Take an elevator to the top (a 1 minute, 14 second ride) for fantastic 360-degree views of Vermont, Massachusetts, and New York. Open Mid April through October, 9-5, $5 adults, $1 kids.
VISIT: Old First Church
The first church in Vermont “dedicated to the separation of Church and State,” this congregation was established in 1762, and the church erected in 1806.
You’ll find the burial place of America’s rural poet, Robert Frost, behind this quintessential New England house of worship in “Vermont’s Sacred Acre” – the cemetery out back.
Frost, who was born in 1874 and died in 1963, is buried with many family members. His gravestone is engraved with the parting words, “I had a lover’s quarrel with the world.”
VISIT: The Bennington Museum
Most people come to this art and history museum to see the largest collection of Grandma Moses paintings in the world.
But The Bennington Museum is branching out in new directions. Over the last few years, it’s added more mid-century modern art and is “filling in the blanks” about “Gilded Age” Vermont (1890’s – 1920’s), when an industrial boom drew an influx of wealthy mill owners.
You’ll find one of only twenty 1924 Martin-Wasp Motorcars ever made, and portraits of women in their finery.
The museum’s original building was in a former Catholic Church – a rare instance of “adaptive reuse” when The Bennington first opened in 1928. Built in 1855, the church became too small for the growing number of Irish and Italian workers who streamed to the region to work in the mills.
The original building remains an old-world glass curio-case “Church Gallery,” indicative of museums of yore. As such, it is chock a block with stuff. Find marble slabs, radios, pottery, weathervanes, clocks, statuary and even bobbins and lace – all representing goods made or sourced here.
But of course, you’re here to see Grandma Moses art. Born the year Abe Lincoln was assassinated and passing away the year JFK was assassinated, Anna Mary Robertson Moses was a late blooming, self-taught artist who started painting “the simple farm life” in earnest at age 78. She proved that you are never too old to follow your passions.
The museum has incorporated Moses’ one-room schoolhouse into its structure as a hands-on gallery for kids. Open June through October, 7 days a week from 10 a.m. to 5 p.m. (closed July 4), February14 through May and November through December, every day except Wednesday from 10 a.m. to 5 p.m., $12 admission.
VISIT: Bennington Center for the Arts/Covered Bridge Museum
Known for its offbeat classes – such as The Birds of Prey Carving Class – the Bennington Center for the Arts is also home to a series of galleries where most art is for sale. Don’t miss two galleries upstairs that house a well-rounded Native American Art collection.
A wing of the Bennington Center for the Arts, the quirky Covered Bridge Museum is a joy to anyone who has ever appreciated the beauty of a wooden bridge.
In 1841, one British travel journalist wrote, “The timber bridges of America are justly celebrated.”
Through photos, videos, and scale models, this museum celebrates every aspect of them, from engineering to craftsmanship. All were built without computers or modern machinery. There’s an exhibit about haunted spots and one on “Edifice Wrecks” – the effects of earth, air, fire and water on bridges that could not be preserved. Open May-Dec, Wed-Mon 10-5. Jan-April, Fri-Sun 10-5. $9 adults, under 12 free.
VISIT: Hemmings Motor News
Nearly a quarter million fans of antique and prestige cars around the world receive this monthly publication, printed right here in Bennington VT. Yes, Jay Leno is a fan.
But there’s also an antique car museum “out back” (in a large retrofitted truck garage), an automotive goods store, and old-fashioned pumps where amazingly, you can still gas up your ride. Museum open June-October, 10-3 daily, free.
SHOP: The Apple Barn
On Route 7 as you approach Bennington from the South, The Apple Barn is often the first place visitors stop when coming into town or passing through. Though its got one of the largest apple orchards in the state, you can’t pick ‘em yourself.
But you can pick from dozens of varieties and apple iterations in baskets and on shelves in this fun place. Don’t miss Apple Barn’s famous Cider Donuts- a true first taste of Vermont.
SHOP: Bennington Potters
Bennington Potters is the LLBean of pottery – a Vermont institution since 1948. Take a self-guided tour of the production facility, and then shop in the vast, colorful clay arts emporium. Though it costs nothing to browse, it might be tough to leave without purchasing at least a hand-crafted mug.
SHOP: Bennington Galleries
Bennington’s got a cute downtown – Bennington Arts Guild (BAG), Hawkins House Crafts and Jewelry, Cake Gallery, and Crazy Russian Girls Bakery are all worth exploring.
Must-See Attractions from Bennington VT to Manchester VT on Historic Route 7A
VISIT: Robert Frost Stone House Museum
A bit forlorn, Frost’s house and barns are nevertheless gripping in their semi-distressed state. One gathers that this is the way Frost lived – his gaze outward over the fields and forests that surround the property.
You understand his poetry a bit better here – it’s where he wrote one of his most popular poems, Stopping By the Woods on A Snowy Evening. I have promises to keep, and miles to go before I sleep. Open Wed-Sun 10-5, $6.
STOP: Sugar Shack/Norman Rockwell Exhibit
Discover this Maple-Syrup maker/bakery/condiment Sugar Shack a few miles north of Arlington VT. Norman Rockwell lived here for 14 years before moving to Stockbridge MA.
Obviously, Rockwell enjoyed the simple, rustic life of Small Town America.
Escaping from the societal dictates of New Rochelle NY to a small home in Vermont, Rockwell relied on his country-neighbors to model for his paintings.
Sugar Shack employees say that Rockwell’s subjects show up at the shop from time to time. You just might meet one. A 15 minute film of Rockwell’s life is shown continuously when the shop/museum is open.
Restaurants in Bennington VT
EAT: Allegro
Brick walls, candlelight, colorful art, it’s rustic-cozy with excellent cuisine. Order the Warm Spinach Salad followed by Crispy Chicken and Risotto – topped with grilled mushrooms and pan roasted tomatoes – or other innovative specials.
With most entrees priced in the $18-$23 range, you can go ahead and order a bottle of nice Italian red without breaking the bank.
EAT: Kevin’s
Housed in the former North Bennington Post Office, the casual-country Kevin’s has become both a local and “second home” favorite.
Owned by a very community-minded couple (Kevin trains other chefs), servings are generous, prices are low, and the food is fresh and good. Salads (including a “Shrimp Caesar”) are $7-$14, Fish and Chips $9, Entrees $10-$19. Come early or late on weekends – there’s always a line out the door.
EAT/BREAKFAST: Blue Benn
This little blue diner has been a Bennington icon for years. Many travelers and second-home owners make this their first stop in town every year.
EAT: Locals also recommend – Lil’ Britain for authentic British fish and chips, Madison’s Brewery Pub and Restaurant, Pangaea in N. Bennington for affordable comfort food.
Where to Stay in Bennington VT
STAY: The Four Chimneys Inn
The Four Chimneys, a grand, Federal style 11-room inn, has been lovingly maintained by the charming and welcoming Lynn and Pete Green. The inn is perfect for visitors who are seeking the Victorian-age “summer in the mountains” experience along with lightening fast wi-fi access.
Each room, painted in soothing pastel colors, is uniquely beautiful. Room 1 features a carved four poster bed, fine antique furniture, hard-wood floor covered by floral rugs, gas fireplace, and a flat screen tv hidden behind a painting (that swings open like a door).
The large bathroom is delightful with a glass shower, tiny crystal chandeliers over a Jacuzzi, and a distinctive copper sink. It’s a room made for romance or peaceful solitary pursuits.
The cocktail bar downstairs (available for guests only) is a favorite of repeat visitors, who look forward to socializing in a comfortable setting.
Open from 5:30pm-9:30pm, this “living room” bar invites conversation among strangers. You can also choose to take your drink outside to the awning-covered patio overlooking the front lawn. The landscape is lovely even when it’s raining.
In the morning, an excellent, made to order hot breakfast is served in a beautifully elegant dining room; a true indulgence. Room rates from $139-$449 per night include a full breakfast, coffee and water available 24/7, wi-fi and parking.
STAY/BUDGET: Harwood Hill Motel
New owners would love to change the name of this funky little place (right on Route 7a) to Art Motel. Each room – with one deeply colored wall, features local art that guests can purchase. There are also programs for painting and woodworking classes – given on a lawn with gorgeous views of the mountains. Rooms from $105 per night.
More Weekend Getaways In Vermont
- Greater Brattleboro VT: Groovy Art, Beer, and Heifers Aplenty
- Manchester VT: Off-Roading Fly-Fishing, Clay Shooting, and The Perfect Bra
- Grafton VT: Sky Magic and Irreverent History
- Okemo Valley Region VT: It’s Not All About The Hill
Be sure to check out Bringing You Vermont when you are downtown. We are located right next to Allegro’s. Every item in our shop is actually manufactured right in Vermont- much of it locally. We are also known for our cafe which pumps out a variety of hand pies, salads, beverages and baked goods daily. Welcome to VT. It is worth a trip from anywhere. We hope you enjoy your stay.
Also be sure to stop into Fiddlehead at Four Corners — the old bank with new art — on the northwest corner of Downtown Bennington and admire two dozen local artists as well as those studio artists from around the country. Pottery. Glass. Jewelry. Oils. Acrylics. Wood. Banned Books case. Photography. Granite. Fabrics. And while you’re here, sit on the bench and play our 1936 Story & Clark piano. Joel and Nina Lentzner, who have owned Fiddlehead since 2000, Thank You for your support!
Mention seeing this article and receive 10% off your order in store! Sugar Shack is located at 29 Sugar Shack Lane in Arlington, VT 05250
And Bennington is home to Vermont’s oldest independent bookstore: The Bennington Bookshop. Since 1928, still going strong.
Thanks for the tip, Phil! Malerie
You guys are awesome! I got the word out there! Malerie