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Bennington, Vermont: Where Fun and Adventure Collide – The Ultimate Guide to the Best Things to Do and Places to Visit

Take the elevator. The Bennington Battle Monument stands 306 feet and there are 412 steps inside it, which is a great deal more staircase than most people want. The observation tower up there opens onto the whole valley, and that is what you came for. The Green Mountains carry over 900 miles of trail for anyone who wants to earn it properly. Mount Snow runs 600 acres of skiable terrain besides that.

Welcome to Bennington, Vermont, a charming town in the southwest corner of the state. With a long history and an abundance of outdoor activities, cultural events and culinary delights, Bennington suits a weekend getaway or a longer vacation exactly. History buff, art lover or adventure seeker, there is a version for everyone in Bennington.

If you are interested in history and heritage, be sure to visit the Bennington Battle Monument, which commemorates the Battle of Bennington during the American Revolution. You can also take a walking tour of the town’s historic sites, the Old First Church and the Robert Frost Stone House Museum included. For art and culture, the Bennington Museum belongs on any list, showing the works of regional artists and running exhibits on Vermont history and culture.

For outdoor adventures, head to the Green Mountains, where you can hike, bike or ski on miles of trails and take in the striking views. You can also work through the area’s lakes and rivers by canoe or kayak, or try your hand at fly fishing. And when it comes to culinary delights, Bennington carries plenty, farm-to-table restaurants through to craft breweries and cideries. Be sure to check out the local farmers’ market for fresh produce and artisanal products.

Key Takeaways

• Bennington, Vermont offers a variety of activities for history buffs, art lovers, and outdoor enthusiasts.
• Must-visit attractions include the Bennington Battle Monument, the Bennington Museum, and the Green Mountains.
• Be sure to sample the local cuisine, including farm-to-table restaurants and craft breweries.

History and Heritage

If you are a history buff, then Bennington suits you exactly. The town is steeped in history, from the Revolutionary War to the present day. Here are some of the stronger historical sites to visit in Bennington:

The Revolutionary War and the Battle of Bennington

Bennington played a key role in the Revolutionary War, and the Battle of Bennington was a turning point in the war. The battle took place on August 16, 1777, and it was a decisive victory for the American forces. You can pick up more about the battle and the war at the Bennington Battle Monument/Observation Tower, which stands 306 feet tall and opens onto striking views of the surrounding area.

Walking Through Old Bennington

Old Bennington is a charming historic district that is home to many fine old homes and buildings. You can take a leisurely stroll through the district and admire the architecture, or you can take a guided walking tour to pick up more about the history of the area.

The Old First Church

The Old First Church is one of the oldest churches in Vermont, and it carries a long history dating back to the 1760s. The church is still in use today, and it is a strong place to visit if you are interested in history and architecture.

Robert Frost Stone House Museum

If you are a fan of poetry, then you will not want to miss the Robert Frost Stone House Museum. The museum sits in the house where Robert Frost lived from 1920 to 1929, and it is a fascinating place to visit if you are interested in the life and work of this famous poet.

Bennington Battle Monument/Observation Tower

As mentioned earlier, the Bennington Battle Monument/Observation Tower belongs on any list for anyone interested in the history of the Revolutionary War. The tower opens onto striking views of the surrounding area, and it is a strong place to take photos.

Park-McCullough House

The Park-McCullough House is a fine old mansion that was built in 1865. The house is now a museum, and it is a strong place to pick up more about the history of Bennington and the surrounding area.

So, there you have it, some of the stronger historical sites to visit in Bennington. The Revolutionary War, architecture or poetry, there is a version for everyone in this charming Vermont town.

Art and Culture

If you are a fan of art and culture, Bennington carries plenty. Here are some places that belong on any art enthusiast’s list:

The Bennington Museum

The Bennington Museum is a great place to start your art and culture tour. The museum has an extensive collection of over 30,000 artworks, artifacts, documents, photos, and weapons. It boasts the largest public collection of Grandma Moses paintings, and the old schoolhouse where she attended is now part of the museum. You’ll find a range of exhibits here, from contemporary art to historical artifacts.

Grandma Moses Paintings

Speaking of Grandma Moses, if you are a fan of her work, you will not want to miss the chance to see some of her paintings up close. The Bennington Museum holds the largest public collection of her work, but you can also find some of her paintings in other places around town, such as local art galleries.

Art Galleries in Bennington

Bennington is home to several art galleries, showcasing the work of both local and visiting artists. Some galleries to check out include The Left Bank Gallery, The Bennington Arts Guild, and The Vermont Arts Exchange. You never know what kind of art you’ll discover in these galleries, so be sure to stop by and take a look.

Oldcastle Theatre Company

If you’re more interested in performing arts, the Oldcastle Theatre Company is a great place to catch a show. This professional theatre company produces a range of plays and musicals throughout the year, showcasing local talent as well as visiting performers. From classic dramas to contemporary comedies, there’s always something interesting happening at Oldcastle.

Fan of visual art or of the performing arts, Bennington carries plenty. Grandma Moses paintings through to local art galleries and professional theater productions, you are sure to find something that speaks to you. So go ahead, indulge your creative side and work through the art and culture of Bennington.

Outdoor Adventures

If you are an outdoor enthusiast, Bennington suits you exactly. With its striking scenery and endless possibilities for outdoor recreation, you will never run out of things to do. Here are some of the stronger outdoor adventures you can have in Bennington:

Hiking in the Green Mountains

The Green Mountains are exactly what a hiker wants, and Bennington is the perfect base for working through them. With over 900 miles of trails, you can choose from easy strolls to challenging hikes. Some of the stronger trails include the Long Trail, the Appalachian Trail and the Robert Frost Trail. Do not forget to bring your camera to capture the striking views.

Lake Shaftsbury State Park

If you are after a place to cool off on a hot summer day, head to Lake Shaftsbury State Park. This fine lake suits swimming, fishing and boating exactly. There are also plenty of picnic areas and hiking trails to work through. And if you are lucky, you might even spot some wildlife, such as beavers, otters and herons.

Kayaking in Vermont’s Waterways

Vermont is home to some of the stronger kayaking and canoeing in the country, and Bennington is no exception. Beginner or experienced paddler, you will find plenty of chances to work through the state’s waterways. Some of the stronger places to paddle include the Battenkill River, the Walloomsac River and Lake Paran.

Skiing and Snowboarding at Mount Snow

If you are a winter sports enthusiast, you will not want to miss Mount Snow. With over 600 acres of skiable terrain, this mountain carries a version for everyone, beginners through to experts. And if skiing or snowboarding is not your thing, there are plenty of other winter activities to settle into, such as snowshoeing, ice skating and tubing.

So grab your hiking boots, kayak or skis, and get ready for some outdoor adventure in fine Bennington.

Summer gets you the trails. The Long Trail, the Appalachian Trail and the Robert Frost Trail all run out of here, from easy strolls through to serious climbs. Winter belongs to Mount Snow, with snowshoeing, skating and tubing alongside. The Garlic Festival lands in September and Winterfest lands in February, so the calendar covers both ends. Lake Shaftsbury State Park handles the hot days in between the two.

Culinary Delights

Looking for some delicious food in Bennington? You are on the right page. Here are some of the stronger culinary delights that you should try.

Breakfast at the Blue Benn Diner

Start your day with a hearty breakfast at the Blue Benn Diner. This diner is a local favorite and has been around since 1948. You can settle into classic breakfast dishes such as pancakes, waffles and eggs benedict. But if you are feeling adventurous, try their famous “Garbage Plate”, a delicious combination of home fries, eggs and your choice of meat, all smothered in cheese and gravy. Do not forget to grab a slice of their homemade pie before you leave.

Dining at Kevin’s Sports Pub and Restaurant

If you are after a fun and casual dining experience, head over to Kevin’s Sports Pub and Restaurant. This place suits sports fans exactly, as they have TVs all around the restaurant showing the latest games. They serve classic pub food such as burgers, wings and nachos, but they also run some unusual dishes like their famous “Mac Attack Burger”, a burger topped with mac and cheese, bacon and BBQ sauce. Wash it down with one of their many craft beers on draft.

Savoring Vermont’s Famous Creemee

No trip to Vermont is complete without trying a creemee. These soft-serve ice cream treats are a Vermont staple and can be found at various creemee stands around town. One of the stronger places to try a creemee in Bennington is at the Chocolate Barn. They carry a wide selection of flavors and toppings to choose from, so you can make your own creation. Do not forget to take a selfie with your creemee and share it on social media.

So, in the mood for a classic breakfast, a fun pub experience or a sweet treat, Bennington has got you covered.

Shopping and More

If shopping is your thing, then Bennington, Vermont has got you covered. With its charming downtown area and unusual shops, you are sure to find something that catches your eye. Here are a few places you should check out:

Downtown Bennington Historic District

Take a stroll down Main Street and work through the Downtown Bennington Historic District. This area is home to a variety of shops, antique stores, art galleries and specialty shops included. You can find everything from handmade crafts to vintage clothing to gourmet foods. And do not forget to stop by the Bennington Farmers’ Market on Saturdays from May to October for fresh produce and local goods.

Fiddlehead at Four Corners

For a one-of-a-kind shopping experience, head to Fiddlehead at Four Corners. This eclectic shop runs a mix of vintage and new items, clothing, jewelry, home decor and more included. You never know what you will find at Fiddlehead, but that is part of the fun. And if you are lucky, you might catch a live music performance or art exhibit while you are there.

Bennington Lanes and Cinemas

If you are after some indoor entertainment, check out Bennington Lanes and Cinemas. This family-friendly venue runs bowling, arcade games and a movie theater all in one place. You can bowl a few frames, play some skee-ball, and then catch the latest blockbuster on the big screen. And if you are feeling hungry, grab a bite to eat at the snack bar.

Shopping, bowling or catching a movie, Bennington, Vermont carries a version for everyone. So grab your wallet and get ready for some fun.

Frequently Asked Questions

What’s the best way to conquer the Bennington Battle Monument?

Well, we suggest taking the elevator to the top instead of climbing the 412 steps. Unless you are training for a marathon, of course. The view from the top is worth the ride. Do not forget to snap a few photos for the ‘gram.

Looking for a family-friendly activity in Bennington? Any suggestions?

Why not check out the Bennington Museum? It carries a version for everyone, art through to history through to local culture. Plus, they run a strong gift shop for souvenirs. And do not worry, they will not kick you out if your kids start running around like wild animals.

Where can I find the most delicious eats in Bennington?

Well, that is a tough one. There are so many strong restaurants in town. But if we had to pick just one, we would say go to Blue Benn Diner. It is a classic, and their pancakes are legendary. Plus, it is open 24 hours, so you can get your fix anytime.

What’s the most interesting thing about Bennington that most people don’t know?

Did you know that Bennington was once home to a secret government project during World War II? It was called the Bennington College War Games and it was used to train military leaders. Now that is some serious history.

Are there any upcoming events in Bennington that I shouldn’t miss?

Absolutely. Check out the Garlic Festival in September. It is a stinky good time. And do not miss the Winterfest in February. It suits bundling up and settling in with some hot cocoa exactly.

Is it true that Bennington has some of the most picturesque covered bridges in Vermont?

You betcha. The Silk Road Covered Bridge and the Paper Mill Village Bridge are both worth a visit. And if you are feeling adventurous, take a drive down the Shushan Covered Bridge Road and see how many you can spot.

Frequently asked questions about Bennington, Vermont

Which museum in Bennington holds the Grandma Moses paintings?

The Bennington Museum, and it holds the largest public collection of them anywhere at all. She painted late in life and she painted a great deal, and the museum built its whole reputation on holding more of it than anyone else. The rest of the collection covers regional artists alongside exhibits on Vermont history and its culture. Local galleries around the town carry a few of her paintings as well. Start there.

Which trail near Bennington is the longest?

The Long Trail, and it is easily the older of the two big ones. It runs the whole length of Vermont, and Bennington sits close enough to the southern end of it to make a decent base. The Appalachian Trail shares part of its route through this stretch. The Robert Frost Trail is the short one, named after the poet who lived here from 1920 to 1929. Roughly 900 miles.

Which covered bridge near Bennington is worth seeing?

The Silk Road Covered Bridge, if you are only seeing one of them. The Paper Mill Village Bridge is the other one worth stopping for, and the two of them sit close enough together to pair up. Shushan Covered Bridge Road runs past several more, if you want to make a drive of it. Vermont built these things because a roof kept the timbers dry and the bridge itself standing. Cheaper than rebuilding.

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