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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, so 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 for those interested in art and history. More than enough museums within the town 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 can 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.
- Things to Do in Bennington, Vermont
- 1. Bennington Battle Monument
- 2. Bennington Museum
- 3. Visit Downtown Bennington
- 4. Visit Bennington’s Historical Covered Bridges
- 5. “Old First” Congregational Church
- 6. Robert Frost Stone House Museum
- 7. Oldcastle Theatre Company
- 8. Park-McCullough Historic House
- 9. Hike Vermont’s Long Trail
- 10. Bennington College
- 11. Lake Shaftsbury State Park
- 12. Benner’s Bagels Pizza N’ What Nosh
- 13. The Publyk House
- 14. Kevin’s Sports Pub and Restaurant
- Places to Stay in Bennington
- What is the best thing to do with kids in Bennington, Vermont?
- What are some fun things to do in Bennington, Vermont?
- What are some things to do in Bennington, Vermont, when it’s raining?
- What are the best tourist attractions in Bennington, Vermont?
- 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
Things to Do in Bennington, Vermont
1. Bennington Battle Monument
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 must purchase a ticket from the gift shop for $1 to $5, depending on age. 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 to buy souvenirs for your friends and family.
Bennington Battle Monument is a convenient place to visit since public restrooms and easy parking exist. 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: Things to Do in Burlington, Vermont
2. Bennington Museum
Address: 75 Main St, Bennington, VT 05201
This museum in southern Vermont gives you a glimpse of the state’s rich history. In this museum, you will find all types of historical art and works from local artists, such as paintings, pottery, and even old furniture.
This is one of the best Vermont state historic sites that allow you 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. You can get yourself or your loved ones some unique artifacts to remember from here.
But, if you want a real museum experience, you can take a guided tour. With a guided tour, you can experience the 10-acre park and the 14 galleries with various 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.
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3. Visit Downtown Bennington
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.
Walking downtown, 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 much 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 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: Things to Do in Stowe, Vermont
4. Visit Bennington’s Historical Covered Bridges
Address: 475 River Rd, North Bennington, VT 05257
Bennington’s three covered bridges are all near one another. The address is for the first bridge, the Burt Henry Covered Bridge. You can access the other two from west to east: the Paper Mill Village Bridge and the Silk Road Covered Bridge.
The Burt Henry Covered Bridge is a town lattice truss bridge 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 attractions 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: Things to Do in Vermont & Places to Visit
5. “Old First” Congregational Church
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, 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. 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 is a quaint graveyard where 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.
You can also enjoy some old structures from the Old Church, 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.
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6. Robert Frost Stone House Museum
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, which 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 run by Bennington College. Apart from visiting the museum, the grounds are also very attractive. The beautiful Robert Frost trail also covers 2 miles through the woods and the stone walls.
Visiting the trails will give you an idea of Robert Frost’s life and the environment. You can even envision Robert Frost walking here back in the day. The trail will lead you to Lake Paran, one of the major attractions in North Bennington.
See Related: Things to Do in Montpelier, Vermont
7. Oldcastle Theatre Company
Address: 331 Main St, Bennington, VT 05201
If you want to experience the city’s artistic side, visit the Oldcastle Theatre Company. The theater has produced over 300 shows, which 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.
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8. Park-McCullough Historic House
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 discussing 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 glimpse this historic building.
See Related: 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, crossing peaks at Stratton and Bromley for approximately 100 miles in Vermont.
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: Things to Do in Middlebury, Vermont
10. Bennington College
Address: 1 College Dr, Bennington, VT 05201
Bennington College must feature When discussing places to visit in this small town because it is a significant part of its history. The college started in 1932 and 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 to walk around while exploring Bennington.
See Related: Where To Stay In Stowe
11. Lake Shaftsbury State Park
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 to just relax on the lake’s beautiful sandy beach. And if you are looking for good hiking trails, the park has one – 1 mile around the lake.
Lake Shaftsbury State Park is undoubtedly among Bennington, Vermont’s best places to visit. The park is also close to 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
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, where the guests can relax while enjoying their pizza. Apart from serving pizza, they have sandwiches, soups, and salads.
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13. The Publyk House
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 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 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.
See Related: Where to Stay in Burlington
14. Kevin’s Sports Pub and Restaurant
Address: 27 Main St, North Bennington, VT 05257
When visiting a small town like Bennington, bars and restaurants are quite significant. They have a rich history and are great places for locals to meet and interact. Kevin’s Sports Pub and Restaurant is a brick building that was constructed in 1903 and is a fantastic place.
It was originally a restaurant and meat marketplace but 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.
Places to Stay in Bennington
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.
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 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.
What is the best thing to do with kids in Bennington, Vermont?
The best thing to do with kids in Bennington is to visit the 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. These include visiting the historical bridges, the Old First Congregational Church, or the Covered Bridge Museum. You can also 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. There are numerous things to do here when it’s pouring. For instance, the Bennington Museum is an ideal place to visit.
You can admire this place’s incredible art pieces 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 historic bridges, and the Old First Congregational Church. These are just some tourist attractions that draw people to this city.
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Kyle Kroeger is the Founder and Owner of ViaTravelers.com. He is a full-time traveler and entrepreneur. Kyle started ViaTravelers.com to help travelers experience a fully immersive cultural experience as he did initially living in Italy. He’s a converted finance nerd and Excel jockey turned world wanderer (and may try to get lost on purpose). After visiting 12 countries and 13 national parks in a year, he was devoted to creating and telling stories like he’d heard.
Plus, after spending more time on airplanes and packing, he’s learned some incredible travel hacks over time as he earned over 1 million Chase Ultimate Rewards points in under a year, helping him maximize experiences as much as possible to discover the true meaning of travel.
He loves listening to local stories from around the world and sharing his experiences traveling the globe. He loves travel so much that he moved from his hometown of Minneapolis to Amsterdam with his small family to travel Europe full-time.