Awesome Family-Friendly Things to Do in Bennington, VT

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Bennington, Vermont, is a quaint New England town that offers a variety of family-friendly activities. Whether you’re looking for indoor or outdoor adventures, there are plenty of kid-friendly things to do in Bennington, VT.

Bennington has something for the whole family, from museums and theaters to hiking trails and parks.

Bennington also has points of interest and parks, including the Green Mountain National Forest, which offers miles of scenic trails for all skill levels.

Whether looking for a relaxing stroll or a challenging hike, you will love Bennington.

Where is Bennington, VT?

Bennington is the largest town in Southern Vermont, located near New York and Massachusetts borders. It is the home of the Battle of Bennington, the Bennington Battle Monument, and Bennington College.

Top Attractions for Kids

When planning a family vacation to Bennington, Vermont, finding activities to keep your kids entertained and engaged is important. Luckily, many fun things to do in the area will appeal to children of all ages.

Here are some of the top attractions for kids in Bennington.

Outdoor Activities

Like all of Vermont, Bennington is surrounded by natural beauty, making it a great destination for families who enjoy spending time outdoors. These fun outdoor activities are sure to get your family outside and exploring.

  • Hiking Trails: Several hiking trails in and around Bennington are suitable for families with kids. The Harmon Hill Trail, for example, offers stunning views of the town and is an easy hike that kids will love.
  • Biking: If your family enjoys biking, you can rent bikes and explore the area’s scenic bike paths. The Bennington Area Trail System (BATS) is a popular network of trails that offers a variety of routes for all skill levels.
  • Fishing: Bennington is home to several lakes and rivers that are great for fishing. Kids will love spending a day on the water, casting a line, and trying to catch some fish.
  • Retreat Farm: visit the animals at the farm, jump and play at the Forest Playground, and discover a new story every month on the Storybook Walk.
  • Chocolatorium: located in nearby East Arlington, stop in to can learn about the history and science of chocolate and buy some delicious treats.

Historical and Cultural Sites

Bennington, Vermont, is a town full of history and culture. Visitors of all ages can enjoy exploring its many historical and cultural sites.


If the weather isn’t cooperating, or if your family prefers indoor activities, you might enjoy visiting one of Bennington’s museums.

  • The Bennington Museum is a great place to start if you want something educational. The museum offers a variety of exhibits, including a collection of Grandma Moses paintings and a gallery dedicated to the history of Vermont.
  • The Dollhouse and Toy Museum of Vermont features a collection of over 1,000 dolls and dollhouses that kids will love.

The Bennington Battle Monument

Check out the Bennington Battle Monument if you want a fun outdoor activity. This monument commemorates the Battle of Bennington, which took place during the Revolutionary War.

From May to October, kids will love climbing to the top of this 306-foot monument commemorating the Battle of Bennington, a pivotal event in the American Revolution.

While at the top, take in the stunning view from any direction. There is also an elevator that makes the top of the monument accessible to everyone.

The Bennington Monument also has bathroom facilities and a cute little gift shop.

Historic Churches

New England is well-known for its beautiful churches. You will find one in the center of almost every town in the region, and Bennington has several historic churches worth visiting.

The Old First Church is the oldest in Vermont, dating back to 1805. It features beautiful stained glass windows and a historic cemetery.

The Sacred Heart St. Francis de Sales is another notable church featuring stunning architecture and a peaceful atmosphere.

Old Cemeteries

This might sound a bit morbid, but old cemeteries are a hallmark of New England. The Old Bennington Cemetery is a fascinating place to explore, with graves dating back to the 1700s.

Your family can learn about Bennington’s early settlers and notable residents, including poet Robert Frost, who is buried here.

Points of Interest

In addition to these sites, Bennington has several other points of interest that families will enjoy.

Bennington Potters has a gorgeous selection of handmade pottery pieces such as bakeware, dishes, mugs, and more. This unique shop is great for picking up some high-quality souvenirs and gifts.

The Bennington Farmers’ Market is another popular destination, featuring fresh produce, baked goods, and crafts from local vendors.

Covered Bridges

New England is well known for its old wooden covered bridges, and Bennington County is no exception.

  • Paper Mill Village Bridge is the longest covered bridge in Bennington County and is a great place to stop for a beautiful photo op. You can also walk across the bridge and enjoy the view of the Wallosmac River below.
  • The Henry Covered Bridge is a must-see, with its picturesque setting and historic charm.
  • The Silk Road Covered Bridge was built in 1840 and is the oldest covered bridge in Bennington County. It is one of several covered bridges located within two miles. The bridge crosses the Wallosmac River to connect downtown Bennington and the village of North Bennington.
Photo Credit: Doug Kerr | Creative Commons license

Exploring Bennington

There is plenty to do for a laid-back vacation, weekend, or day trip. Here are some of the best kid-friendly things to do in Bennington, VT.

Downtown Bennington

Downtown Bennington is a great place to start your visit. Stroll along Main Street and check out the shops, restaurants, and galleries.

There are also family-friendly places to grab a bite to eat.

Hiking Trails

No matter which season you plan your visit, Bennington is home to several beautiful trails.

  • Harmon Hill Trail takes you to a lookout point with stunning town views and surrounding mountains. The trail is easy to moderate and is suitable for kids of all ages.
  • Robert Frost Trailhead, named after the famous poet who lived in the area, is a beautiful trail to hike with kids to get some exercise and fresh air.

Map of Bennington

A local guidebook is especially helpful to make the most of your visit to Bennington. This will help you navigate the area and find all the best attractions and activities.

You can also pick up a map of Bennington at the Bennington Chamber of Commerce or any local hotel.

Nearby Attractions

One of the many wonderful things about New England is that the states are small, so visiting a location or attraction in a neighboring state is often a reasonable drive away.

If you’re looking for more family-friendly activities in the general area, plenty of nearby attractions are worth checking out.

Here are some of our top picks broken down by location:

North Bennington

North Bennington is a charming village located just a few miles north of Bennington, with several family-friendly attractions worth checking out.

  • Park-McCullough Historic House: This stunning Victorian mansion is a must-see for history buffs and architecture enthusiasts.
  • Lake Paran: This beautiful lake is perfect for swimming, fishing, and boating in the summer.

Bromley Mountain

Bromley and Mountain Adventure Park in nearby Peru, VT. offers lots of fun family-friendly activities such as an alpine slide, climbing wall, mini golf, and more. For a more thrilling experience, the Treetop Adventure Course is perfect for the true adventure lover as well as plenty of outdoor activities, hiking, biking, and skiing.


Located about an hour and a half north of Bennington, Stowe is a charming town known for its skiing and outdoor activities. Here are some of the top attractions in the area:

  • Stowe Mountain Resort: This ski resort is one of the best in the region and offers plenty of activities for families in both the winter and summer months.
  • Bingham Falls: Located in Smuggler’s Notch State Park, Bingham Falls is a popular waterfall known for its beauty and easy access, making it a fun hike for families.
  • Smugglers’ Notch State Park: This beautiful park is perfect for hiking, camping, and picnicking.

Lake George

Lake George, NY, while not technically in Vermont, New York, is just a short drive from Bennington and offers plenty of family-friendly attractions. Lake George is about an hour and a half Northwest of Bennington.

This beautiful lake is perfect for swimming, boating, and fishing in the summer.

New Hampshire

New Hampshire is another neighboring state with plenty of family-friendly attractions. Here are some of the top picks:


Located about an hour and a half north of Bennington, Burlington, Vermont is a bustling college town with plenty of family-friendly activities.


Located about an hour east of Bennington, Manchester is a charming town known for its shopping and outdoor activities. Here are some of the top picks:

  • Hildene: This historic mansion was once home to Abraham Lincoln’s son and now offers tours and events.
  • Equinox Preservation Trust: This organization offers many outdoor activities, including hiking, mountain biking, and snowshoeing.
Things to do in The Berkshires with kids


Located just south of Vermont, Massachusetts is another neighboring state with plenty of family-friendly attractions.

  • The Berkshires: This beautiful region is perfect for hiking, skiing, and exploring the outdoors.
  • Six Flags New England: This amusement park is perfect for thrill-seekers and features plenty of rides and attractions.
  • Norman Rockwell Museum: This museum features a wide variety of artwork by the famous illustrator and is perfect for art enthusiasts.

Final Thoughts

Bennington is a great destination for families looking for a vacation or weekend away that’s off the beaten trail. With a wide range of activities and attractions, you won’t have a problem finding something fun to do in this charming Vermont town.

Bennington has it all if you are looking for outdoor adventures, cultural experiences, or just some good old-fashioned family fun. From the historic downtown area to the beautiful surrounding countryside, there are plenty of activities waiting for your family.

Bennington is a wonderful destination for families looking for a fun and memorable vacation. With so much to see and do, it’s no wonder it’s become a popular spot for families from all over New England and beyond.

So, whether you’re planning a family vacation, a day trip, or just looking for something fun to do with the kids, be sure to add Bennington to your list of must-visit destinations. We hope you enjoy your time in this beautiful and historic town!

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