15 Best Things to Do in Bennington, VT

Bennington, VT
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As the third-largest town in Vermont, Bennington is home to several attractions to catch the eye of any potential traveler.

It cherishes a storied history and is now home to many landmarks and tourist hotspots, enticing people from all over to grow its community.

Even if you’re just passing through, you’ll still find cool places to hang out on your journey.

Experience Bennington through its people.

Watch live musicians or performers in one of Bennington’s theaters.

Marvel at the progress of history as you gaze at the 306-foot Bennington Battle Monument, built to remember the Battle of Bennington in 1777.

Live it all in Bennington, a city overflowing with the riches of history and the pleasures of arts and culture.

Who knows? You might like the place enough to make you want to settle down there.

Interested in everything Bennington, VT, has to offer? Check out the list below.

Relive History at the Old First Church

While you retrace history, see the bigger picture by checking out the oldest church in Vermont and the state’s first Protestant church.

Gathered in 1762, The Old First Church was home to many of Bennington’s first milestones as a community.

Outside View of the Old First Church
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Its first settlers orbited the Meeting House, built in 1763, and went on to the current church, built in 1805.

To honor the church’s heritage, the Vermont Legislature named the building as “Vermont’s Colonial Shrine.”

Scratch your itch for history with the surrounding revolutionary-era homes and green mountain views.

You can find The Old First Church at 1 Monument Circle, Bennington, VT 05201.

Grab Some Beer and Grub at the Madison Brewing Co.

A day’s walk along Bennington’s historical sites would leave anyone hungry.

So, head over to The Madison Brewing Co. to sit down with your friends over the fizz of craft beer and the sizzle of delicious food.

From an old storefront in downtown Bennington, The Madison Brewing Co. has grown into one of the city’s hotspots for drinks and food.

Beer lovers from all over will surely appreciate their diverse selection of top-quality beers, from New England Style IPAs to the classic Old-world style concoctions.

Cap off your day at The Madison Brewing Co., located at 428 Main Street, Bennington, VT 05201.

Take the Road Less-Traveled at the Robert Frost Stone House Museum

Outside View of Robert Frost Stone House Museum
Rolf Müller (User:Rolfmueller), CC BY-SA 3.0, via Wikimedia Commons

If you like poetry, chances are you’ve already read Robert Frost’s popular work “Stopping by Woods on a Snowy Evening.”

Why not round out your Frost experience by stopping by the house where the poet wrote his masterpieces?

Built in 1769, the stone and timber house itself is a historical landmark since it is one of the few examples of Dutch Colonial architecture.

Inside View of Robert Frost Stone House Museum
Rolf Müller (User:Rolfmueller), CC BY-SA 3.0, via Wikimedia Commons

Even when the great poet lived there, from 1920 to 1929, he left the place untouched. You can even find many of the original apple trees planted by Frost outside the house.

To complete your literary history tour, you can also visit the great poet’s gravesite, located just a few minutes away.

Visit the Robert Frost Stone House Museum at 121 Historic Route 7A, Shaftsbury, VT 05262.

Break Out the Clubs at the Mt. Anthony Country Club

Eager to get in some golf swings while in Bennington? The Mt. Anthony Country Club, an 18-hole championship golf course, has got you covered.

Right in the heart of Old Bennington lies Vermont’s oldest public country club, the Mt. Anthony, established in 1897.

Its position within the Green Mountains also gives golfers breathtaking views of the surrounding landscape.

What better view to celebrate your hole-in-one than a bright expanse of lively green?

The Mt. Anthony Country Club also offers event hosting services. Don’t know where to tie the knot?

The scenic country club will make you fall in love all over again during your wedding ceremony.

The Mt. Anthony Country Club is located at 180 Country Club Drive, Bennington, VT 05201.

See Live Performances at the Oldcastle Theatre Company

You can find one of America’s longest-running professional theatre companies right here in Bennington.

Founded in 1972, the Oldcastle Theater Company has been putting on electrifying performances for decades.

Theatergoers will have plenty to choose from Oldcastle’s repertoire of classic theatre, insightful new plays, and present-day hits.

The theatre aims to make theater accessible to audiences everywhere.

Don’t even worry about pricing.

The Oldcastle Theatre Company offers reasonably priced tickets, so you can catch performances whenever you want.

Thanks to their efforts, Oldcastle has become a vital part of Bennington’s arts and culture scene.

Catch live shows at the Oldcastle Theatre Company, located at 331 Main Street, PO Box 1555, Bennington, VT 05201.

Know Your History at the Bennington Museum

Outside view of Bennington Museum
Daderot, CC0, via Wikimedia Commons

It’s rare to find a museum that’s as much a historical landmark as the artifacts it holds. But the Bennington Museum is one such building.

Since its opening in 1852, the museum has regaled visitors with various collections of art and historical artifacts.

Exhibit in Bennington Museum
Daderot, CC0, via Wikimedia Commons

For example, you can see the world’s largest collection of paintings made by the great American folk artist Anna Mary “Grandma Moses” Robertson only at the Bennington Museum.

You can also see other major artifacts in the museum’s permanent exhibit. One of them is the famous Bennington Flag, one of the oldest “Stars and Stripes” flags in existence.

Visit the museum at 75 Main Street, Bennington, VT 05201.

Interior View of Bennington Museum
Daderot, CC0, via Wikimedia Commons

Eat Hearty Meals at the Walloomsac Farmers’ Market

If you’re tired of eating out in Bennington, go to the Walloomsac Farmers’ Market right away.

Buy an armful of fresh ingredients so you can prepare a nice home-cooked meal for yourself, your friends, or your family.

The Walloomsac Farmers’ Market also offers only fresh produce.

In fact, you’ll get them a mere 24 hours after harvest.

What’s more, buying at the market also brings you closer to the greater Bennington community.

Thinking about adopting a healthy diet?

Knowing about where your food comes from and how it is grown can help you decide.

Who better to teach you about healthy eating than vendors at the farmers’ market?

If you go to the Walloomsac Farmers’ Market in summer, you’ll find them at 100 Veterans Memorial Drive, Bennington, VT 05201.

Meanwhile, if you visit in winter, go to 650 Main Street, Bennington, VT 05201.

Cross the Silk Road Covered Bridge

View of Silk Road Covered Bridge
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One of the five covered bridges in Bennington County, the Silk Road Covered Bridge is special because of its historical significance and because it allows tourists to take in spectacular riverside views.

Built by Benjamin Sears in 1840, the bridge is just one of Bennington’s many historical sites.

It was also added to the National Register of Historic Places in 1973. Surely, one of the reasons it’s been standing so long is its presence in the middle of lush and serene nature.

Tourists can take photos of the single-lane bridge or the surrounding areas. Complete your photo roll by visiting the Silk Road Covered Bridge.

What makes the Fiddlehead at Four Corners Gallery unique is that it was transformed from an old marble bank into a haven for artwork.

A burst of inspiration made them graffiti the old vault, and the rest is history.

But that doesn’t mean they changed the place completely.

In fact, they retained the bank’s original architecture—the marble bank counters still stand while the brass chandelier still hangs.

Visit the gallery to look at artwork like oil paintings and film photography, as well as crafts like pottery and blown glass.

You can find the Fiddlehead at Four Corners Gallery at 338 Main Street, Bennington, VT 05201.

Ride the Wind at Kimberly Farms

For nearly 30 years, Kimberly Farms have provided travelers with an easy and fun horse-riding experience.

If you’ve been nursing dreams of being a cowboy, now you know where to go.

You’ll have a whole 60 acres of space to roam with your horse.

Likewise, you can enjoy traveling through pastures, seeing wildlife, and traipsing along horse-riding tracks.

Don’t even worry if you’re a novice.

Kimberly Farms always gives you expert guides who will teach you how to ride horses well.

While on horseback, you can enjoy the views of the mountains and countryside to your hearts’ content.

Fulfill your cowboy dreams at Kimberly Farms, located at 1214 Cross Hill Road, North Bennington, VT 05257.

Get Lost in the Park-McCullough Historic Governor’s Mansion

Outside View of Park-McCullough Historic Governor’s Mansion
Doug Kerr, CC BY-SA 2.0, via Wikimedia Commons

In the mood for more historical sites? Then get up and go over to the Park-McCullough Governor’s Mansion.

One of Bennington’s best-preserved Victorian-era mansions, the house has 35 rooms and covers 200 acres.

The house is too big that you can’t appreciate all of it without a guide.

Marvel at the historic opulence on display from the rich blend of Second Empire Style and Romantic Revival architecture.

Besides guided tours, the mansion also offers event hosting services as well as cultural activities.

Hold your wedding here and feel like classy gentlemen and ladies in your finest couture.

The Park-McCullough Governor’s Mansion can be found at 1 Park Street, North Bennington, VT 05257.

Knock Down Some Pins at the Bennington Bowling Lanes

Tired of doing touristy stuff for an entire day?

You need to hit up the Bennington Bowling Lanes when you’re done touring.

The family-run bowling lanes has been open since 1980, and it is one of the best bowling alleys in town.

With 18 lanes to choose from, you don’t need to worry about waiting times.

Once you’re done bowling, you can unwind with some drinks at the bar or have a bite out of their extensive menu.

Head over to the Bennington Bowling Lanes at 219 Northside Drive, Bennington, VT 05201.

Stretch Your Legs at the Robert Frost Trail

The renowned poet lends his name to another Bennington landmark, the Robert Frost Trail.

Hiking along this two-mile stretch will make you sweat.

However, the view over Lake Paran and the sweeping vistas covering the Bennington Battle Monument and the Berkshires will make the effort worth it.

Follow the trail and enter the deep woods near Paran Creek, passing under stone cliffs.

Then, you’ll come across the pine stand planted by Robert Frost himself in the 1920s.

When you feel like resting, sit on the benches at the trail’s mid-point located at the footbridge over Paran Creek.

You can enter the Robert Frost Trail from both the west and the east access points.

From the west, you’ll enter near the Lake Paran swimming area. From the east, you’ll start near the Robert Frost Stone House Museum.

Visit the Bennington Battle Monument

Statue in Bennington Battle Monument
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The Bennington Battle Monument is the most popular historical attraction in town. Go there to remember the decisive Battle of Bennington, fought in 1777 during the American Revolutionary War.

Standing at 306 feet, the monument calls on tourists to remember the bravery of the American heroes who fought for independence.

You can’t help but feel a shot of pride when you stand under the structure.

The Bennington Battle Monument can be found at 15 Monument Circle, Bennington, VT 05201.

Catch the Sunshine at the White Rocks Trail

Feeling up to more walking? The White Rocks Trail is another hike you can enjoy with friends or family.

Follow along the 2,400-foot shoulder of Bald Mountain and be awestruck by the panoramic view of Vermont.

After a while of walking, you’ll pass through the Glastenbury Wilderness and then finally reach the peak of the White Rocks.

Enjoy the peace and bliss of reaching the mountaintop and feel the vastness of nature by catching the sunset.

Start hiking up the White Rocks Trail, located at 449 NorthBranch Street, Bennington, VT 05201.

Final Thoughts

History buffs will definitely enjoy a trip to Bennington, Vermont.

However, nature and art lovers will still have a good time visiting the galleries, theaters, and hiking trails spread across town.

Why not book your trip to Bennington today?