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14 Fun & Best Things to Do in Bennington, Vermont 

14 Fun & Best Things to Do in Bennington, Vermont 

Whether you are traveling alone, as a family, or with friends, there are numerous fun things to do in Bennington, Vermont. And whether you seek adventure or somewhere to just cool your head, Bennington is the place.

Bennington, Vermont, is just 3.5 hours from New York City. This makes it a convenient place to visit for many city residents looking for a quiet time. Also, it is a small but welcoming town, and that means that life is not as busy as in cities like New York and Boston.

Bennington sets itself apart by being an outdoor-activities hub in Southwestern Vermont. It is also a great place to visit for those interested in art and history. There are more than enough museums within the town that offer a great experience for history enthusiasts.

If you love experiencing nature and the outdoors, this is one of the greatest places to visit in the region. Various outdoor activities like nature walks, hiking, camping, and access to cross-country skiing in the Bennington area make up a typical New England vacation.

When the weather is just right, you will have a chance to enjoy mountain sunsets and experience natural beauty in its purest form.

But where do you start? Well, stick around as we dive deep into what makes Bennington oh so charming.

The Harwood Hill
1. The Harwood Hill Top Recommendation

The Harwood Hill is a motel located in Bennington, Vermont. It offers comfortable accommodation with a garden and free WiFi throughout the property. The motel is set within 4 miles of Bennington Battle Monument and 31.1 miles of Rensselaer Polytechnic Institute. Each room features air conditioning, satellite TV, heating and an en suite bathroom with a shower.

Hampton Inn Bennington
2. Hampton Inn Bennington

Ideally located off I-90 in Bennington, the Hampton Inn is just a short distance from downtown and offers easy access to many attractions. The hotel is also situated close to the area's renowned ski resorts, including Catamount Ski Area. Several hiking trails can be accessed from the property and guests can enjoy a game of tennis on site or take advantage of free access to the indoor pool and fitness centre.

Knotty Pine Motel
3. Knotty Pine Motel

Knotty Pine Motel is located in the heart of scenic Vermont, just 20 minutes’ drive from historic Bennington. Free Wi-Fi access and a cable TV are offered in each simply decorated room. Guests can unwind on the outdoor terrace or by the pool. A microwave, refrigerator and hairdryer are provided as standard in every guest room at Motel Knotty Pine. The motel is 5 minutes’ drive from Bennington Museum and 7 minutes’ drive from Bennington Center for the Arts.

TLDR

  • Most significant landmark – Bennington Battle Monument
  • Best park – Lake Shaftsbury State Park
  • Best free activity -Visit Downtown Bennington
  • Best activity for kids – Bennington Museum
  • Best activity for adults – Oldcastle Theatre Company
  • Best food – Benner’s Bagels Pizza N’ What Nosh
  • Best nightlife – Kevin’s Sports Pub and Restaurant
  • Best all-around accommodation The Harwood Hill

Fun & Best Things to Do in Bennington, Vermont

1. Bennington Battle Monument

Bennington Battle Monument
By King of Hearts – Own work, CC BY-SA 4.0,

Address: 15 Monument Cir, Bennington, VT 05201

This historical monument is a must-see while visiting Bennington. It is a 306-ft. tall structure made with a slender stone column that commemorates the famous Battle of Bennington in the Revolutionary War. And, it’s a marvel.

The column dates back to 1877 when a historical society began planning to build a monument for the battle’s centenary. And although private homes currently surround the Bennington monument, you can still easily find it.

You can reach the top using an elevator, but it has around 470 stairs that are currently closed. Before going up the elevator, you need to purchase a ticket for $1 to $5, depending on age, from the gift shop. And once you reach the top, the city’s beautiful scenery, from all directions, is quite captivating.

At the base of the Bennington Battle Monument, there is a little museum that allows you to learn about the history of Vermont. There is also a gift shop where you can buy souvenirs for your friends and family.

Bennington Battle Monument is a convenient place to visit since there are also public restrooms and easy parking. Plus, the beautifully manicured grounds make walking around and taking pictures close to the monument easier. And if you are looking for accommodation near this place, Four Chimneys Inn will serve you well.

See Related: Fun & Best Things to Do in Burlington, Vermont

2. Bennington Museum

Bennington Museum
By Daderot – Own work, CC0,

Address: 75 Main St, Bennington, VT 05201

This museum in southern Vermont gives you a glimpse of the rich history of the state. In this museum, you will find all types of historical art and works from local artists, such as paintings, pottery, and even old furniture.

In fact, this is one of the best Vermont state historic sites that give you a chance to explore the history and culture not found in a typical Vermont vacation.

When visiting the Bennington Museum, you will also get a chance to shop for different gifts and artifacts. From here, you can get yourself or your loved ones some unique artifacts to remember.

But, if you want to get a real museum experience, you can opt to take a guided tour. With a guided tour, you can experience the 10-acre park plus all the 14 galleries with all kinds of genealogical resources.

One of the main attractions of the Bennington Museum is the collection of Anna Mary Robertson’s “Grandma” Moses paintings. Kids from all over the world enjoy this 20th-century folk artist. The museum has something important to learn for everyone, including kids.

Art lovers will also enjoy the experience since this is a very artistic museum with a rich history. Many historical collections in the Bennington museum date from the mid-19th century to the 20th century.

See Related: Route 100 Vermont Itinerary

3. Visit Downtown Bennington

Downtown Bennington, VT
By Daniel Case – Own work, CC BY-SA 3.0,

Address: 215 South St, Bennington, Vermont 05201

When visiting Downton Bennington, wear your favorite walking shoes. This is because the experience is better when you take a walking tour. For instance, you can take a self-guided tour of this small town from Putnam Square to Walloomsac River.

When taking a downtown walk, you will see many nice places, including shops and great places to eat. And besides shopping and eating, you will learn a lot of history about the town.

Downtown has a lot of history about Bennington, from the textile mills to railroads. You can walk around to experience the history or drive around. However, we recommend walking since you will get a chance to visit as many places as possible.

Among the best things to see here is the Downtown Welcome Center, which dates back to the 1840s. Initially built as a blacksmith shop, it has now become a welcome center for city visitors.

The historical Bennington county courthouse is also a good place to visit. The courthouse was constructed in the 1930s and had that colonial look with a triangular entrance portfolio.

You can also visit the historic 210 south street garage that dates back to 1926. This was later remodeled in 1969 but has maintained its original look with arched windows and neo-classical colors.

See Related: Fun & Best Things to Do in Stowe, Vermont

4. Visit Bennington’s Historical Covered Bridges

Silk Road Bridge
By Famartin – Own work, CC BY-SA 4.0,

Address: 475 River Rd, North Bennington, VT 05257

Bennington’s three covered bridges are all near one another. The address provided is for the first bridge, the Burt Henry Covered Bridge. From west to east, you can access the other two: the Paper Mill Village Bridge and the Silk Road Covered Bridge.

The Burt Henry Covered Bridge is a town lattice truss bridge that was originally built in 1840 but rebuilt in 1989. The bridge has a total of 37 meters and a width of 5.6 meters. And if you want good access to the river, you can do that through this bridge.

The Paper Mill Village Bridge is also a historic bridge dating back to 1889. It is the longest bridge covering 1.2 miles of driving distance. In 2000 the bridge was remodeled, but it has still maintained most of its historic features.

The third bridge is the Silk Road Covered Bridge, which dates back to 1840 and covers 0.6 miles in driving distance. It is a covered bridge and remains one of the main attraction features in the area.

Both kids and adults will enjoy visiting the covered bridges. And if you want to learn more about the covered bridges, you can take a detour to the Covered Bridge Museum. It’s the only museum of its kind, and from here, you can get anything you want to know about these amazing bridges.

See Related: Best Things to Do in Vermont & Places to Visit

5. “Old First” Congregational Church

Old Bennington First Old Church
By Doug Kerr from Albany, NY, United States – Bennington, VermontUploaded by Magicpiano, CC BY-SA 2.0,

Address: 60 Monument Ave, Bennington, VT 05201

The first old church is a favorite location for visitors from far and wide. It is considered one of the most photographed buildings in the world for a good reason. The place is beautiful and especially when you visit during the leaf-peeping season.

This church has been around since the 1800s, making it one of the best historic buildings to visit. You can even attend Sunday service when you visit, which starts at 10 am in the summer months, and 11 am for the rest of the year.

Outside the church, there is also a quaint graveyard where some of the famous residents like Robert frost were buried. If you love art and history, you will learn a lot about the graveyard that still looks intact to date.

From the Old Church, you can also enjoy some more old structures, like the Jedidiah Dewey House, as you walk through Monument Avenue. These will surely take you some decades back in time, a feeling that is not always easy to find.

See Related: Fun & Best Things to Do in Seattle, Washington

6. Robert Frost Stone House Museum

Robert Frost Stone Museum
By Rolf Müller (User:Rolfmueller) – Own work, CC BY-SA 3.0,

Address: 121 Historic Rte 7a, Shaftsbury, VT 05262

Robert Frost was one of the most famous residents of Bennington, Vermont. Those interested can visit the Robert Frost grave, as he was buried in the Old Bennington Cemetery next to the Old First Church. But he had a residential home that has become a museum.

The stone house, now a museum, is currently run by Bennington College. Apart from visiting the museum, the grounds are also very attractive. There is also the beautiful Robert Frost trail covering 2 miles through the woods and the stone walls.

Visiting the trails will give you an idea of the life Robert Frost lived and the environment. You can even envision Robert Frost walking here back in the day. And the trail will lead you all the way to Lake Paran, one of the major attractions in North Bennington.

See Related: Fun & Best Things to Do in Montpelier, Vermont

7. Oldcastle Theatre Company

Oldcastle Theatre Company
Image by Tripadvisor

Address: 331 Main St, Bennington, VT 05201

If you want to experience the city’s artistic side, you need to visit the Oldcastle Theatre Company. The theater has produced over 300 shows, so it is quite big and significant in the town.

This theater is over 50 years and has always been supported by the locals. However, this is not just a local theater. It is run by professionals such as actors and producers, and they always give high-quality productions.

Five New York actors started this theatre. They decided to establish it in Vermont because one of the actors lived in the area. This theater has been active since 1972, and it remains a significant part of Bennington’s art and history.

See Related: Best Spring Break Destinations for Families

8. Park-McCullough Historic House

Park-McCullough Historic House
By Doug Kerr, licensed under CC BY-SA 2.0,

Address: 1 Park St, N Bennington, VT 05257

Architecture is always a big part of any city, and the Park-McCullough House cannot be left when we talk about Vermont’s history. This is one of the best-preserved Victorian mansions in New England and is a great place to visit if you want to get inspiration on architecture and interior design.

The house was built in 1864-1865, but it stands to date. It sits on over 200 acres of big land, and you can always tour the grounds when visiting the historic house. It is a significant part of the town’s architecture and has been preserved in historical style.

The best thing about it is that you can tour the house on any weekend when summer starts until the fall foliage season ends. So, time your vacation within this time if you want to get a glimpse of this historic building.

See Related: Fun & Best Things to Do in Brattleboro, Vermont

9. Hike Vermont’s Long Trail

Address: Various access points in both Bennington and the surrounding towns

Vermont’s Long Trail is the oldest long-distance hiking trail in the United States. Can you imagine hiking on the first long-distance trail in the US? Well, Bennington, Vermont, offers you just the perfect opportunity.

The trail follows the main ridge of the Green Mountains from the Vermont-Massachusettes border up to Canada. Even more interesting, this trail shares a path with the Appalachian Trail, for approximately 100 miles in Vermont, crossing peaks at Stratton and Bromley.

Therefore, if you’ve been looking for exciting places for long hikes, try the Long Trail – it will certainly satisfy your urge to hike.

See Related: Fun & Best Things to Do in Middlebury, Vermont

10. Bennington College

Bennington College
By Jared C. Benedict. – Full resolution original available at., is licensed under CC BY-SA 2.0,

Address: 1 College Dr, Bennington, VT 05201

When talking about places to visit in this small town, Bennington College must feature because it is a significant part of its history. The college, which started in 1932, was initially a college for women.

The college grounds are big, covering 440 acres of land. Visitors can take self-guided tours of the location to explore the school’s rich history. On the college buildings, you will get a brief history of the place by reading the walls. It is a good place if you want to walk around while exploring Bennington.

11. Lake Shaftsbury State Park

Lake Shaftsbury State Park
Lake Shaftsbury 10.07.06” by NancyCz is licensed under CC BY-NC-SA 2.0.

Address: 262 Lake Shaftsbury Rd, Shaftsbury, VT 05262

No vacation is complete without visiting a nice park. Lake Shaftsbury State Park offers such an opportunity while touring Bennington, Vermont.

The park encompasses over 26 acres of land, with a massive wetland on one end, famous for birding activities. During summer, travelers also visit the place for swimming, picnics, or just to just relax on the lake’s beautiful sandy beach. And if you are looking for some good hiking trails, the park has one – 1 mile around the lake.

Lake Shaftsbury State Park is undoubtedly among the best places to visit in Bennington, Vermont. The park is also close to other attractions like the Bennington Museum and the Covered Bridge Museum. As such, you can easily combine a visit to the park with other activities in the area.

The park is open all year round, but the best time to visit is during summer when all the features are open and accessible. So, while in Bennington, Vermont, make a point of visiting this park.

12. Benner’s Bagels Pizza N’ What Nosh

Benner's Bagels Pizza N' What Nosh

Address: 604 Main St, Bennington, VT 05201

Do you wish to taste some of the town’s finest cuisine? Benner’s Pizza is your spot. The pizzeria has been running for over 35 years in an old structure built in 1861. Although this is an old building, it still maintains many of its historic features, which are quite stunning.

For instance, the front porch has been preserved, and this is where the guests can relax while enjoying their pizza. And apart from serving pizza, they also have sandwiches, soups, and salads.

See Related: Best Places for Fall Colors

13. The Publyk House

The Publyk House
The Publyk House by Ron Patla is licensed under CC BY-NC-SA 2.0

Address: 782 Harwood Hill Rd, Bennington, VT 05201

The Publyk House in Bennington is a big part of the local community. The house has been open to the public for over 40 years and remains a good place for interaction and fine dining. It is a good place to visit if you want to experience some fine dining.

The Publyk House is a three-story barn with a warm and welcoming ambiance. And during cold months, the guests can get warmth from a brick hearth that keeps everyone warm.

If you are traveling alone and you are looking for somewhere to meet strangers, this is a great place to visit. The place’s ambiance allows you to interact easily with other guests.

14. Kevin’s Sports Pub and Restaurant

Kevin's Sports Pub Bennington
Image by Tripadvisor

Address: 27 Main St, North Bennington, VT 05257

When visiting a small town like Bennington, bars and restaurants are quite significant. They carry a rich history and are great places where locals meet and interact. Kevin’s Sports Pub and Restaurant reside in a brick building that was constructed in 1903 and is one such fantastic place.

It was originally a restaurant and a meat marketplace, but it was recently upgraded to a pub. If you want to experience American classics, this is a great place to visit and experience the local favorites. Your nights in Bennington can get a bit more lively by visiting this place.

FAQ

What is the best thing to do with kids in Bennington, Vermont?

The best thing to do with kids in Bennington is to visit Bennington Museum or the different historical bridges. The museum offers a perfect opportunity for you and the kids to learn about the art and history of the city. On the other hand, the bridges offer a variety of activities to do, such as fishing, kayaking, or just cooling off in the river.

What are some fun things to do in Bennington, Vermont?

There are a number of fun things to do in Bennington, Vermont. Some of these include visiting the different historical bridges, the Old First Congregational Church, or the Covered Bridge Museum. You can also take a walk through Monument Avenue to enjoy some more old structures. Or, you can simply enjoy the scenic views that the city has to offer.

What are some things to do in Bennington, Vermont, when it’s raining?

The rains don’t have to stop you from enjoying what the city offers. In fact, there are numerous things to do here when it’s pouring. For instance, the Bennington Museum is an ideal place to visit.

Here you can admire all the incredible art pieces in this place or learn more about the city’s rich history without worrying about the rains.

What are the best tourist attractions in Bennington, Vermont?

Here, the list is long. However, some of the best places to visit include the Bennington Museum, the different historical bridges, and the Old First Congregational Church. These are just some of the many tourist attractions that draw people to this city.

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