15 Unforgettable Things To Do In Bennington VT – Green Mountain Gateway

Bennington, Vermont, isn’t just another quaint New England town. It’s a vibrant blend of historic sites, artistic communities, and natural splendors. Whether you’re visiting Southern Vermont for the weekend or planning an extended stay, you’ll find no shortage of captivating experiences here.

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.

Looking for more weekend getaway ideas? Here’s our roundup of romantic getaways in New England.

Where Is Bennington VT?

Situated in southwestern Vermont, in Bennington County, the historic town of Bennington is about a three-hour drive from Boston and roughly the same distance from New York City. It’s an hour away from Albany, New York, making it easily accessible for a weekend getaway.

This charming town is framed by the lush Green Mountains to the east and the Taconic Range to the west, offering a picturesque setting that exemplifies Vermont’s natural beauty. Rich in history, arts, and outdoor activities, Bennington serves as both a cultural hub and a gateway to some of the state’s most stunning landscapes.

Things To Do In Bennington VT

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.

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 1800s 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.

VISIT: Old First Church

The first church in Vermont was “dedicated to the separation of Church and State,” this congregation was established in 1762, and the church was 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 passed 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.

VISIT: Bennington Center for the Arts

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.

SHOP: Downtown Bennington

Old-world charm meets modern-day convenience in Downtown Bennington. Find handmade crafts from studio artists at Fiddlehead at Four Corners. For book lovers, there’s Vermont’s oldest bookstore, the indie Bennington Bookshop, offering a range of titles and friendly service. Don’t miss Katie Cleaver Metalsmith, where you can explore an astonishing collection of handcrafted jewelry, intricately designed by Katie Cleaver herself, showcasing the craftsmanship that Bennington is known for.

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.

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.

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.

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 it’s 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.

GO: Lake Paran

Surrounded by lush forests and rolling hills, this freshwater lake offers a range of activities to suit all tastes—from kayaking and fishing to simply lounging on its sandy shores. The lake’s calm waters are ideal for paddleboarding or a leisurely swim, and nearby hiking trails beckon explorers with the promise of scenic vistas.

SHOP: The Bennington Farmers Market

The Bennington Farmers Market is a vibrant gathering spot that epitomizes Vermont’s community spirit. Held on Saturdays, the market is a must-visit for anyone looking to delve into the local culture. You’ll find a rich array of fresh produce, artisanal cheeses, homemade jams, and baked goods that taste like they’re straight out of Grandma’s kitchen. Craft vendors also display handmade soaps, jewelry, and other unique finds. It’s not just a place to shop; it’s an experience complete with live music, food trucks, and yoga sessions.

HIKE: The Mile Around Woods

The Mile Around Woods hiking trail in North Bennington is a local favorite for nature walks. This relatively flat loop trail offers an easy and scenic excursion, winding through mature hardwood forests and open meadows. Along the way, you’ll encounter charming wooden bridges and enjoy views of the surrounding hills. It’s an ideal spot for families, dog walkers, or anyone looking to escape into nature without venturing too far from the comforts of town.

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,

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: South Street Cafe & Bakery

South Street Cafe and Bakery is more than just a spot to grab a quick coffee; it’s a hub of activity and comfort in Bennington. The establishment serves as a meeting place for locals and a welcoming pit stop for visitors exploring the town. From ethically sourced coffees and handcrafted lattes to a selection of freshly baked pastries, the menu leaves nothing to be desired.

Artwork from local creators graces the walls, while the cozy interior complete with plush sofas and eclectic decor offers a respite from the day’s adventures. Whether you’re looking for a caffeine fix, a spot to catch up on some reading, or a warm atmosphere to enjoy good conversation, South Street Cafe and Bakery is the place to be.

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. Come early or late on weekends – there’s always a line out the door.

EAT/BREAKFAST: Blue Benn Diner

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.

Bennington VT Hotels

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 lightning-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.

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

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