11 of the Best Things to do in Bennington VT

Looking for a Vermont destination with a walkable downtown, great restaurants, intriguing shops, and lots of outdoor recreation? Not only does Bennington, Vermont cover all of these bases, but it’s incredibly easy to get to.

Located just three and a half hours from New York City, three hours from Boston, and an hour from Albany, Bennington is the gateway to Vermont, and well worth a visit no matter where you’re coming from.

I may be biased, but I think Bennington is one of the loveliest places to visit in all of Vermont.

Beautiful places in Vermont are pretty easy to come by, and the natural beauty in and around Bennington is what made me fall in love with it more than 15 years ago. In fact, I’ve lived in Bennington longer than anywhere else, and I can’t imagine calling any other place home, no matter how much I love a good road trip!

Whether you’re looking for a girlfriend getaway, a romantic weekend for two, or a family vacation, there is so much to do in Bennington VT. While we seriously doubt you’ll run out of things to do in Bennington, you can also make it your home base and explore some of the nearby attractions and towns.

Ready to explore the oh-so-charming and welcoming town of Bennington, Vermont? Here are the best things to do in Bennington VT for your next getaway.

The Best Things to do in Bennington, Vermont

With just about 14,000 people, Bennington is a small town bookended by two mountain ranges (the Greens and the Taconics) and surrounded by farms and forests. By Vermont standards, Bennington is actually a big town – the sixth-largest in the state. Bennington is the county seat and a hub of activity in Southwestern Vermont. 

If you love the outdoors, you will fall in love with Bennington, where you can hike, paddle, fish, and mountain bike without leaving town, but there are plenty of other ways to spend your time!

Take a Self-Guided Walking Tour of Old Bennington

While located entirely in the town of Bennington, a visit to Old Bennington, Vermont is a bit like stepping back in time. This historic village is home to less than 200 people, along with beautiful historic buildings, and a most colorful past. 

Whether you’ve lived in the area for years or are visiting for the first time, there’s a lot to discover on an Old Bennington walking tour. The oldest home on the tour is the Jedidiah Dewey House, built in 1763. The homes on the tour are private residences, but it’s fun to meander past them as you tour Monument Avenue.

The Old First Church (pictured above) was built in 1805 and is one of the most beautiful and recognizable churches in Vermont. Download a walking tour brochure to get started on your journey.

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Also Read: Plan a Perfect Winter Weekend in Bennington and Manchester, Vermont

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Eat Breakfast at a Historic Diner

Bennington is home to some fantastic eateries, but one of the most unique is the historic Blue Benn Diner on North Street.

The Blue Benn was manufactured in the late 1940s by The Paterson Vehicle Co. and shipped and assembled here in Bennington in 1948. The diner was owned by Sonny and Marlou Monroe for many decades starting in 1973, and just recently came under new ownership.

Blue Benn serves up classic diner fare along with a few eclectic choices. There are still jukeboxes on every table and plenty of room for you to rub elbows with the locals at the bar.

The Blue Benn is open from Tuesday to Sunday, from 6 am – 2 pm.

Tour Bennington’s Beautiful Covered Bridges

Bennington County is fortunate enough to have five historic covered bridges, and they can all be explored in a single afternoon. These beautiful feats of engineering offer a one-of-a-kind look into a bygone age — a time when ingenious craftsmanship was used to create structures that embodied simple beauty and embraced the natural landscape. 

A covered bridge road trip is the perfect way to spend your afternoon. If you do this trip in the summer, you’ll find great swimming under both Arlington bridges, but fall and winter are beautiful too.

Start by visiting the three covered bridges in Bennington and then drive north to Arlington to see the other two:

• Silk Road Covered Bridge
• Paper Mill Covered Bridge
• Burt Henry Covered Bridge
• Chiselville Covered Bridge
• Arlington Green Covered Bridge

For a complete guide to discovering the covered bridges in Bennington County, read this next:

Go Antiquing in Bennington, Vermont

The Bennington area is home to a half-dozen antique stores, and many of them are located right on Main Street making it easy to walk between them as you search for the one-of-a-kind prize you never knew you needed.

If you’re a fan of antiquing, then Bennington is bound to entice your inner treasure hunter. Check out the following shops:

• Main Street Antiques: 473 Main Street, Bennington
• Monument Vintage: 435 Main Street, Bennington
• G’s Records and Books: 475 Main Street, Bennington
• W. Collective: 332 Main Street, Bennington
• Covered Bridge Antiques: 2026 Route 7A, Bennington

Discover Vermont History and Art at the Bennington Museum

There’s more than one reason to check out Bennington Museum – thought-provoking history and art exhibits, intriguing special events, and even an outdoor nature trail. But Bennington Museum is probably best known for housing the largest collection of Grandma Moses paintings in the world.

Anna Mary Robertson started painting in her seventies and became one of America’s most prolific and famous self-taught artists within just a few years. Come visit the Grandma Moses schoolhouse as well as many artifacts from her painting life.

Bennington Museum presents and explores the rich culture of southern Vermont, eastern New York State, northwestern Massachusetts, and southern New Hampshire in all its forms, from the 18th century to the present.

Between June and November, Bennington Museum is open every day except Wednesday.
Between November and December, it is open Thursday, Friday, Saturday, Sunday, and Monday. from 10 am to 4 pm.

Visit on Friday evenings for Concerts in the Courtyard between June 3 and September 2, when the museum is open until 7 pm.

Take in the View from the Bennington Battle Monument

At 306 feet, the Bennington Monument is the tallest building in the state, and it’s the most popular of all Vermont state historic sites. We love this stately structure so much, that we’ve added it to our list of the very best things to do in Vermont.

If you visit between May and October, you can take an elevator to the top for spectacular views of Bennington and the Green Mountains.

The Bennington Monument was completed in 1889 to commemorate the Battle of Bennington, which took place on August 16, 1777. In that famous battle, Brigadier General John Stark and 1,400 New Hampshire men, defeated two detachments of the British army, who were seeking to capture a store of weapons and food maintained where the monument now stands.

The Bennington Monument is open between May 1 and October 31 on Thursday, Friday, Saturday, Sunday, and Monday from 10 am to 5 pm.

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Historic tidbit: Although the battle is called the Battle of Bennington, it actually took place about 10 miles west in Walloomsac, New York.

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Visit the Former Home and Grave of a Famous Vermont Poet

Did you know that Robert Frost lived in both Bennington and Ripton, Vermont? His Bennington/Shaftsbury home is now the Robert Frost Stone House Museum. Frost lived here from 1920 to 1929, when he wrote “Stopping by Woods on a Snowy Evening.” This lovely museum is run by Bennington College and is open for visitors from Friday through Sunday from 10 am – 4 pm.

While visiting this literary landmark, be sure to walk the grounds, and perhaps the beautiful nature trail that starts behind the barn and heads out to Lake Paran in North Bennington.

The Robert Frost Trail is 2 miles (one-way) and meanders through the woods and along stone walls. It’s easy to envision Robert Frost walking these same country trails before heading home to pen some of his most famous works.

After visiting the Robert Frost House, drive back into Old Bennington where you can pay your respects to Robert Frost at his gravesite behind the Old First Church.

Hike a Part of the Oldest Long-Distance Trail in America

Vermont’s Long Trail in Vermont was the first long-distance hiking trail in the United States and the inspiration for the much longer Appalachian Trail. This 272-mile trail follows the ridgeline of the Green Mountains from the Vermont-Massachusettes state line in the south to the Canadian border in the north.

The Appalachian Trail/Long Trail share a path from roughly 100 miles through Vermont before diverging near Killington. The trail crosses Route 9 in Woodford Vermont.

If you hike south, you can reach Harmon Hill in about 1.5 miles. The hike starts off steep, but after a mile or so, it levels off and travels through a high meadow, finally opening up to awesome views. The hike totals around 3 miles, with a total elevation gain of 1,000 feet.

If you hike north on the Long Trail, you will head up Maple Hill in the Glastenbury Wilderness. This is another steep hike, but without the view at the end. Still, it’s a lovely trek through the woods and worth checking out.

Paddle a Quiet Lake or River Near Bennington

Canoeing and kayaking are both great ways to enjoy the outdoors in Vermont and there are several small lakes and rivers around Bennington that are perfect for paddling. If spending a few hours on the water is your idea of a perfect afternoon, check out these spots.

*Note that Lake Shaftsbury and Woodford State Park both offer canoe and kayak rentals.

• Lake Paran – Lake Paran is a small, 35-acre lake in North Bennington with easy access for canoes and kayaks. The shore is undeveloped and the scenery is lovely. Use the boat launch on State Fishing Acc off of North Street in North Bennington. 
• Lake Shaftsbury State Park – Lake Shaftsbury encompasses 26 acres with a wetland on one end that is great for birding. This is a popular park for summer visitors who come to swim, picnic, and relax on the sandy beach. There’s also an easy 1-mile trail around the lake.
• Woodford State Park – The 23-acre Adams Reservoir is located in Woodford State Park at 2,310 feet above sea level. The shoreline is entirely wooded and there are a couple of private coves that are fun to explore. Be on the lookout for sundews, a carnivorous plant that grows on logs in the marshy part of the lake. A 2.4-mile trail meanders around the lake and is perfect for an afternoon hike.
• Walloomsac River – If you don’t mind doing some car shuffling, the Walloomsac River is a nice easy paddle for a warm day. Put in at the Henry Bridge in North Bennington and paddle downstream to the Edward Cottrell Bridge at the intersection of Cottrell Road and Route 67 in Hoosick Falls, New York.

Drink Up at a Local Brewery or Distillery

Vermont takes its beer very seriously, and Bennington is no exception. Not only does the town host a Summer and Winter Homebrew Festival each year, but several local breweries make exceptional beers as well. You can visit three breweries in downtown Bennington. If you love craft beer, this is one of the best things to do in Bennington VT after hours.

• Harvest Brewing: 201 South Street, Bennington. Open Thursday – Saturday, hours vary.
• Madison Brewing: 428 Main Street, Bennington. Open Monday – Thursday, 11:30 am – 9 pm. Friday – Saturday, 11:30 am – 9:30 pm. Sunday, 11:30 – 4:30 pm.
• Farm Road Brewing: 400 Main Street, Bennington. Open Wednesday and Thursday, 4 – 8 pm, Friday and Saturday, 12 – 8 pm, Sunday, 12 – 6 pm.

In 2021, the Village Garage Distillery opened downtown, serving a full menu, as well as locally-crafted bourbon and vodka. They are located at 107 Depot Street, Bennington.

Tour Park McCullough House in North Bennington

This historic, Victorian-era house was built in 1864 and is considered one of the finest and best-preserved Victorian mansions in New England. You can visit this beauty, the working farm behind it, and the lovely, Mile-Around-Woods hiking trail all in one afternoon. This is one of my favorite places to walk and take pictures, and we always bring visitors from out of state here for picnics.

Give yourself a few hours to tour the mansion and the grounds.

Park McCullough House is open for tours on weekends from summer until the end of fall foliage season. Admission is $15 per person. Special events are also hosted throughout the summer and include concerts, movies, wine tastings, and free yoga in the garden.

How to Get to Bennington, Vermont

Bennington is located in the southwest corner of Vermont, basically right on the border of both New York to the west and Massachusetts to the south. It’s a pretty easy drive from anywhere in the northeast, which is why we recommend it as a great road trip destination.

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Pro Travel Tip: Give yourself 2-3 days to explore all of Bennington, especially if you love the outdoors. If you want to explore some of the surrounding towns like Wilmington or Manchester, plan for at least 4 days.

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If you’re coming from out of state, the closest airport is Albany International, which is an easy one-hour drive from Bennington. Again, maybe it’s a biased opinion, but I adore flying in and out of the Albany Airport and always consider myself very fortunate that it is so close.

The Best Time to Visit Bennington

When you think of a typical Vermont vacation, you are likely thinking about fall and winter. Autumn in Vermont is known for the jaw-dropping foliage that blankets the forests and mountains in colorful displays. And winter, of course, is famous for skiing and snowboarding in the Green Mountains.

I love Vermont in every season, but there’s nowhere I’d rather be than here in Bennington in the summer. We’ve got swimming holes. Creemee stands. Fireflies. Mountain Sunsets. Farmers’ markets. I just wish summer was longer!

Resources for Exploring Bennington, VT

For more of the very best things to do in Bennington VT, check out some of the resources below:

• What to do – The Bennington Chamber of Commerce has a great events page, plus lots of ideas for places to explore while you’re in the area. Vermont Begins Here is the tourism website for the town of Bennington, and the blog has ideas for where to eat, shop, and recreate.

• Where to eat – Want some ideas for where to get some yummy grub? Bennington has lots of choices, but here’s what I’d recommend: Eat breakfast at the Blue Benn Diner, lunch at Madison Brewing Company, and dinner at either Allegro or 421 Craft Bar and Kitchen.

• Where to stay -We love the Four Chimneys Inn for a splurge or a romantic getaway and The Harwood Hill for a budget option. If you want to camp, we highly recommend Woodford State Park.

Finally, there are some really great deals on vacation rentals in the area. This renovated dairy barn in nearby Pownal has a pool and a hot tub, plus it’s great for kids and dogs!

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Have you ever visited Bennington, Vermont? Whether you’re just passing through or planning an extended stay, we think you’ll love this small but bustling village in the southwest corner of Vermont.

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Tara Schatz is a freelance writer, and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, which was released in May 2023.