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Best and Most Exciting Things to Do in Bennington, Vermont

Bennington Battle Monument

Bennington, Vermont – Battle Monument, courtesy of Tony @King of Hearts

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1 Bennington VT Shops and Fun Things to See

Bennington VT Shops and Fun Things to See

Welcome to Bennington, Vermont, where Vermont state historic charm meets modern convenience. Located in the southwest corner of the state, in Bennington County, Bennington, VT offers a delightful blend of quaint shops, delicious dining, and comfortable lodging options. Whether you're seeking unique gifts, a cozy bed and breakfast experience, covered bridges in Bennington or a taste of local cuisine, Bennington has something to offer for everyone. You will find beautiful places to explore and perhaps a hiking trail, or even a peek the collection of Grandma Moses.

The Village of Old Bennington

Molly Stark Trail and Historic Old Bennington marker - Bennington Museum - Bennington, VT - DSC08490 Photo Courtesy of Daderot, CC0, via Wikimedia Commons

Nestled on an elevated ridge overlooking the Walloomsac River valley, the historic village of Old Bennington lies just half a mile west of downtown Bennington proper. The scenic village is book ended by natural landmarks – Mount Anthony's imposing presence looms over the southwest horizon, while Monument Hill's gradual incline elevates the northern reaches. The views and beauty in and around Bennington, will make you fall in love with the area.

Along the eastern edge, the village terrain plunges sharply downward, forming a steep slope toward the river winding below. Together, these distinctive geographical features shape the varied topography and picturesque views that distinguish Old Bennington's unique location.

Bennington College, a Historic Building

Sprawling across 440 acres at the foothills of the Green Mountains, Bennington College is renowned for its stunning natural beauty and architectural splendor. Its campus, run by Bennington College, has garnered national accolades, including being named one of the most beautiful in America by The Princeton Review and among the top ten colleges with the best architecture by Architectural Digest.

Beyond the school's picturesque landscape and distinctive buildings, Bennington's campus has a rich history, having been founded in 1932 as an progressive leader in higher education. The college's unique hillside setting in southern Vermont provides an inspiring backdrop for experiential learning. You're welcome to take a look at Bennington College and is open to visitors.

North Bennington Vermont Explored

In the early 1900s, North Bennington was a thriving village with mills along Paran Creek that shipped goods across the country. At that time, most daily necessities and amenities could be found within walking distance.

Presently, most North Bennington residents commute to jobs outside of the village. While some factories along Paran Creek continue manufacturing operations, several have been repurposed into housing. One mill was converted into an art studio and nightclub for a period, before being redeveloped into stylish apartments.

Key Takeaways:

  • Explore downtown Bennington's historic Main Street filled with charming shops and restaurants and all the best things to enjoy.
  • Discover a vibrant cultural scene with live theater, art galleries, and museums.
  • Experience the Bennington Battle Monument and Bennington Museum.
  • Choose from a variety of unique lodging options, including cozy bed and breakfasts.
  • Immerse yourself in the warm hospitality of Bennington and create lasting memories.
  • The drive from Bennington to New Hampshire is only about 40 minutes away.
  • Bennington is the largest town in the area and high in Vermont standards

Bennington Vermont Tourist Attractions

When visiting the charming town of Bennington, Vermont, there are several must-see tourist attractions that are sure to captivate visitors. One of the most prominent historic sites in the state is the Bennington Battle Monument, which stands tall as a symbol of the Battle of Bennington during the Revolutionary War. The Bennington Monument and it's towering presence offers panoramic views of the surrounding countryside, making it a popular destination for history buffs and nature enthusiasts alike.

For those interested in art and history, the Bennington Museum is a must-visit. This renowned museum showcases a diverse collection of artwork and artifacts that highlight the rich cultural heritage of the region. From American folk art to contemporary works, the museum offers a fascinating glimpse into the past and present of Bennington and its surrounding areas.

As visitors explore the picturesque landscapes of Bennington, they will also come across several historic covered bridges that are worth exploring. The Silk Road Covered Bridge, Henry Covered Bridge, and Paper Mill Village Bridge are just a few examples of the architectural gems that dot the countryside. These beautifully preserved structures offer a unique glimpse into the region's history and provide excellent photo opportunities.


Bennington Vermont Tourist Attractions:

  1. Bennington Battle Monument
  2. Bennington Museum
  3. Silk Road Covered Bridge
  4. Henry Covered Bridge
  5. Paper Mill Village Bridge

Things to Do in Bennington VT

When it comes to things to do in Bennington VT, the options are plentiful. Whether you're an outdoor enthusiast or a history and culture lover, this charming Vermont town has something for everyone. Here are some of the top activities to consider during your visit:

1. Explore the Great Outdoors

Bennington is just one of many beautiful places in Vermont, making it a haven for outdoor activities. Hike through scenic trails in the Green Mountain National Forest, which offers breathtaking views and opportunities for wildlife spotting. Enjoy a leisurely bike ride along the picturesque country roads, or cast your fishing line into one of the many lakes and rivers in the area. For a peaceful picnic or birdwatching experience, head to Lake Shaftsbury State Park or Woodford State Park.

Discover the Bennington Area Trail System (BATS) which is located in the beautiful southwestern corner of Vermont.  BATS was founded by a group of local bikers, runners, and hikers that advocate for multi-use single track trails for the enjoyment of area residents and visitors alike. As the gateway to Vermont, you can explore all of Bennington, including Vermont state historic sites and the famous battle of Bennington history.

2. Immerse Yourself in History and Culture

Discover Bennington's rich history and vibrant cultural scene by visiting its museums, art galleries, and historic sites. Take a trip back in time at the Bennington Museum, which showcases a diverse collection of art and artifacts. Explore the Bennington Battle Monument, an iconic landmark that commemorates the Revolutionary War. Don't miss the Robert Frost Stone House Museum, where you can learn about the life and work of the famous poet.

3. Indulge in Local Delights

While exploring Bennington, take the time to savor the local flavors and culinary delights. Dine at the charming restaurants and cafés that line Main Street, where you can enjoy farm-to-table cuisine and fresh Vermont ingredients. Don't forget to try the famous Vermont maple syrup, which adds a delicious touch to pancakes, waffles, and other local delicacies. And of course, no visit to Bennington is complete without sampling some of the region's renowned craft beers.

Exploring Downtown Bennington

When it comes to experiencing the charm and vibrancy of Bennington, there's no better place to start than downtown. Our historic Main Street is filled with locally-owned shops, offering a wide range of unique gifts, clothing, and crafts. Whether you're looking for a one-of-a-kind souvenir or a special present for someone back home, you're sure to find something that catches your eye.

In addition to the fantastic shopping and dining options, downtown Bennington is also known for its vibrant cultural scene. Catch a live theater performance at one of our local venues, showcasing everything from classic plays to contemporary works. Explore the art galleries and soak in the creative energy of our local artists. Downtown Bennington truly offers a unique and enriching experience for visitors.

After indulging in some retail therapy, why not treat yourself to a delicious meal or a cup of coffee at one of the many restaurants and cafés in downtown Bennington? From cozy diners to trendy eateries, there's something to satisfy every craving. Whether you're in the mood for farm-to-table cuisine, international flavors, or classic American fare, our downtown area has it all. Any time is the best time to visit!

Exploring Downtown Bennington: Must-Visit Places

  • Bennington Battle Monument: Don't miss the chance to visit this towering monument that commemorates the historic Battle of Bennington during the Revolutionary War. Climb to the top for stunning panoramic views of the surrounding area.
  • Bennington Museum: Immerse yourself in art and history at the Bennington Museum, home to an impressive collection of American art and artifacts. From works by Grandma Moses to historical exhibits, there's something to captivate every visitor.
  • Silk Road Covered Bridge: Snap a picture-perfect moment at this picturesque covered bridge, which is a true symbol of Vermont's charm and beauty. Its serene surroundings make it a popular spot for leisurely strolls and romantic walks.

Exploring downtown in and around Bennington is an adventure you won't want to miss. From the charming shops and restaurants to the vibrant arts scene, there's something for everyone in our historic Main Street. Come and discover the heart and soul of Bennington!

The Spooky Side of Bennington and the Infamous “Bennington Triangle”

The Glastenbury area of Southern Vermont has been the subject of mysterious disappearances and odd occurrences for many years. The so-called “Bennington Triangle” is a phrase created by New England author Joseph A. Citro during a public radio broadcast in 1992. It describes a region of southwestern Vermont in which a number of people went missing between the years of 1920 and 1950. The best-known of which is probably that of Paula Jean Welden.

Also, is Bennington's Southern Vermont College haunted by ghosts? Southern Vermont College (formerly known as the Edward Everett Estate)  is located in the village of Bennington, V . He built the Estate as a summer mansion in Vermont. According to legend, not long after the estate was built, Everett’s wife Amy, drowned while swimming.

Attractions Near Bennington VT

Whew…stepping away from the ghost stories and back to reality…

Looking for things to make you fall in love with Bennington? While Bennington itself offers a wealth of attractions to explore, there are also several nearby destinations that are well worth a visit. Whether you're looking for outdoor adventures or unique cultural experiences, these top tourist spots near Bennington are sure to delight.

1. Manchester

A short drive away from Bennington, the town of Manchester is known for its outlet shopping and stunning natural scenery. Spend a day browsing the high-end boutiques and brand-name stores at Manchester Designer Outlets, or take a scenic drive along Route 7A to admire the area's picturesque landscapes. Just a wee bit of a warning…Manchester has some spooky haunted tales of it's own!

2. Vermont Country Store in Weston

If you're in search of a nostalgic shopping experience, look no further than the Vermont Country Store in Weston. This charming store offers a wide range of goods, from old-fashioned candies to practical household items. Take a step back in time as you wander through the aisles and discover unique treasures.

3. Mount Equinox and the Appalachian Trail

Hiking in Vermont

For outdoor enthusiasts, a visit to Mount Equinox is a must. Enjoy breathtaking views from the summit, accessible by car or on foot via the Skyline Drive. If you're up for a longer adventure, the Appalachian Trail runs through the Bennington area, offering hikers the opportunity to explore the region's natural beauty on foot.

These nearby attractions provide additional opportunities for exploration and adventure during your visit to Bennington. Whether you're seeking shopping, natural beauty, or outdoor activities, there's something for everyone just a short distance from this charming Vermont town.

Bennington Vermont Travel Tips

Ok, so are you up for planning a trip to Bennington, Vermont? We've got you covered with some essential travel tips to make your visit smooth and enjoyable. Bennington is where Vermont begins near the southern border and just a few hours from New York City. It's not your typical Vermont vacation!

Bennington is home to everything from the iconic church in Vermont to the best-preserved Victorian mansions in New England. From sightseeing to exploring historical sites, here's everything you need to know:

1. Sightseeing in Bennington VT

One of the highlights of visiting Bennington is the opportunity to explore its many picturesque sights. Start with a visit to the iconic Bennington Battle Monument, a towering structure that commemorates a significant Revolutionary War battle. Take in panoramic views of the surrounding area from its observation deck. You'll enjoy the views of Bennington. Don't miss the Silk Road Covered Bridge, a charming landmark perfect for a leisurely stroll or photo opportunity. And for literary enthusiasts, the Robert Frost Stone House Museum offers insight into the life and works of the renowned poet. The museum is run by Bennington local experts well versed in the history of Vermont.

2. Discovering Bennington's Historical Sites

Bennington is one town rich in history, and there are plenty of historical sites to explore. Visit the Bennington Museum, where you can delve into the region's art and history through its extensive collection. Step back in time at the Old First Church, a beautiful colonial-style church that dates back to the 1800s.

Another must-visit, located in Bennington, is the Park-McCullough House, a stunning Victorian mansion showcasing the opulence of the Gilded Age. These historical sites offer a glimpse into Bennington's past and provide a fascinating cultural experience.

3. General Travel Tips for Bennington Vermont

When planning your trip to Bennington, keep in mind the following travel tips. Firstly, it's recommended to allocate at least 2-3 days to fully explore the area and experience everything it has to offer. As public transportation options are limited, renting a car is the best way to get around and easily access the various attractions and sites.

The Molly Stark Byway is a scenic route that connects the Vermont towns of Brattleboro and Bennington. The byway passes through the Green Mountains, traversing lowland valleys, historic villages, downtown areas, and mountain terrain along the way. 


Before your visit, be sure to check the opening hours and availability of the museums, historical sites, and other attractions you plan to visit. Lastly, it's always a good idea to stay informed about any health and safety guidelines in place during your visit to ensure a safe and enjoyable trip.

Best Places to Visit in Bennington Vermont

When visiting Bennington, Vermont, there are several must-visit places that showcase the best of what this charming town has to offer. From historic landmarks to natural beauty and cultural attractions, there is something for everyone to enjoy. Some of the top things to do and top attractions include covered bridges. Unfortunately, the Bennington Center for the Arts along with the Covered Bridge Museum are now closed indefinitely. 

Sightseeing and Landmarks Bennington Bucket List:

  • Bennington Battle Monument: Standing tall at 306 feet, this historic landmark commemorates the Battle of Bennington during the Revolutionary War. Take an elevator ride to the top for panoramic views of the surrounding area. Vermont history at it's best!
  • Old Bennington Cemetery: Vermont’s oldest cemetery is on Monument Avenue in the historic district of Bennington, next to the Old First Church. 
  • Silk Road Covered Bridge: This picturesque covered bridge is a must-see attraction, offering a glimpse into Bennington's history and providing a beautiful backdrop for photos.
  • Robert Frost Stone House Museum: Poetry enthusiasts will appreciate a visit to the former home of renowned poet Robert Frost. Explore the museum dedicated to his life and works, and take a walk through the nearby woods for inspiration.

Art and Culture:

  • Bennington Museum: Immerse yourself in art and history at this renowned museum, which houses an extensive collection of American folk art, paintings, and sculptures. Don't miss the Grandma Moses Gallery showcasing the works of renowned folk artist Anna Mary Robertson Moses.
  • Downtown Bennington Galleries: Take a stroll through downtown Bennington and explore the various art galleries showcasing local and regional artists. From paintings to ceramics, you'll find a diverse range of art to admire and purchase.

Outdoor Beauty:

  • Lake Paran: Enjoy a peaceful retreat at this serene lake located just outside of Bennington. Take a leisurely walk along the shore or bring a picnic and relax amidst the natural beauty.
  • Glastenbury Mountain: Hiking enthusiasts can tackle the trails of Glastenbury Mountain. With stunning views and diverse flora and fauna, it's the perfect place to reconnect with nature.
  • Southern Vermont Arts Center Sculpture Park: Combine art and nature with a visit to this beautiful sculpture park. Take a leisurely walk through the park and admire the unique sculptures nestled amidst the lush greenery.

These are just a few of the best places to visit in Bennington, Vermont. Whether you're interested in history, art, or the great outdoors, there's something for everyone to enjoy in this charming town.

Bed and Breakfast in Bennington VT

When it comes to finding the perfect place to stay in Bennington, VT, bed and breakfasts are a popular choice. These charming establishments offer a cozy and welcoming atmosphere that allows visitors to truly experience the essence of this beautiful Vermont town.

One notable bed and breakfast in Bennington is the Henry House Inn. This historic inn features comfortable rooms, delicious breakfast offerings, and a convenient location in the heart of downtown Bennington. Visitors can enjoy the warm hospitality of the inn's hosts and explore the nearby shops, restaurants, and attractions.

Another great option is the Four Chimneys Inn. This elegant bed and breakfast is set in a beautiful historic mansion and offers luxurious accommodations, impeccable service, and stunning views of the surrounding mountains. Guests can relax in the inn's spacious rooms, enjoy a gourmet breakfast, and take advantage of the inn's close proximity to downtown Bennington.

If you're looking for a more rustic experience, consider staying at the Knotty Pine Motel & Cabins. This family-owned establishment offers cozy cabins and motel rooms nestled in a peaceful wooded setting. Guests can unwind in nature while still being just a short drive away from the attractions and activities of Bennington.

Discovering the Shires of Southwestern Vermont

The Shires of Southwestern Vermont, a region encompassing Bennington and the surrounding area, is a hidden gem waiting to be explored. With its picturesque landscapes, rich history, and vibrant communities, it offers something for every visitor. Whether you're a nature lover, history enthusiast, or art connoisseur, the Shires of Southwestern Vermont has it all.

One of the best ways to discover the charms of the area is by utilizing the resources of the Southwestern Vermont Chamber of Commerce. The Chamber serves as a guide for visitors, providing valuable information about the attractions, activities, and businesses in the region. Their travel guide offers insights into the best places to visit, eat, and stay, ensuring that you make the most of your time in Bennington and its surroundings.

Exploring the Shires: From History to Art

  • Immerse yourself in the region's rich history at the Bennington Battle Monument, a towering structure that commemorates an important Revolutionary War battle. Climb to the top for panoramic views of the surrounding area.
  • Indulge your artistic side at the Bennington Museum, where you can admire a vast collection of art and artifacts showcasing the region's cultural heritage. Don't miss the Grandma Moses Gallery, dedicated to the renowned American folk artist.
  • Explore the quaint villages and towns that dot the landscape, each with its own unique charm and character. From Manchester's upscale outlets to the artistic community of Dorset, there's always something new to discover.
  • Though their store is closed for now, you can order directly from Bennington Potters who have hand-crafted their products since 1948.

Whether you're a first-time visitor or a seasoned traveler, the Shires of Southwestern Vermont is sure to captivate your heart. So pack your bags, grab a copy of the Bennington Vermont Travel Guide, and get ready to embark on an unforgettable adventure in this beautiful part of New England.

Photo courtesy of Roman EugeniuszWikimedia

How to Get to Bennington, VT

If you're planning a visit to Bennington, VT, it's important to know how to get there. Located in the southwest corner of Vermont, near the borders of New York and Massachusetts, Bennington is easily accessible by various modes of transportation.

If you prefer to travel by car, Bennington can be reached from the Northeast region and is conveniently located along major highways. Albany International Airport is the closest airport to Bennington, located about an hour's drive away. If you're flying in from a major city, you can catch a flight to Albany and then rent a car or take a taxi to Bennington.

For those who prefer public transportation, bus and train connections are available from major cities in the area. Several bus companies provide service to Bennington, making it an accessible destination for those without a private vehicle. Additionally, Amtrak offers train service to nearby stations, with options to continue your journey to Bennington by bus or taxi.


Traveling to Bennington, VT:

  • By car: Take major highways to reach Bennington from the Northeast region.
  • By plane: Fly to Albany International Airport and rent a car or take a taxi to Bennington.
  • By bus: Several bus companies provide service to Bennington.
  • By train: Take Amtrak to nearby stations and continue by bus or taxi to Bennington.

With its convenient location and various transportation options, visiting Bennington, VT is a breeze. Whether you're driving, flying, or taking public transportation, you'll have no trouble getting to this charming Vermont town.


Bennington, Vermont is a hidden gem that offers a delightful blend of history, natural beauty, and charming shops and restaurants. Whether you're a history buff, an outdoor enthusiast, or simply looking to relax and unwind, Bennington has something to offer everyone.

Is Bennington the largest town in Vermont? Actually, it is the second-largest town in Vermont (after Colchester) and the sixth-largest municipality in the state, including the cities of Burlington, Rutland, and South Burlington.

Start your journey in the heart of downtown Bennington, where you can wander along Main Street and explore the locally-owned shops, art galleries, and museums. Don't miss the Bennington Battle Monument, a towering symbol of the town's rich history. And be sure to visit the Bennington Museum, where you can immerse yourself in the art and culture of this vibrant community.

If you're craving outdoor adventure, you won't be disappointed. Surrounding Bennington, you'll find picturesque parks and trails perfect for hiking, biking, and fishing. Lake Shaftsbury State Park and Woodford State Park offer beautiful settings for picnicking and birdwatching.

With a variety of lodging options, including cozy bed and breakfasts, you can rest easy knowing you'll have a comfortable place to stay during your visit. So grab your travel guide, plan your trip to Bennington, and get ready to create memories that will last a lifetime in this charming Vermont town.

FAQ – Frequently Asked Questions

What are some must-see attractions in Bennington, Vermont?

Some must-see attractions in Bennington include the Bennington Battle Monument, the Bennington Museum, the Silk Road Covered Bridge, the Henry Covered Bridge, Paper Mill Village Bridge, and the Robert Frost Stone House Museum.

What activities can visitors enjoy in Bennington, VT?

Visitors can indulge in outdoor activities such as hiking, biking, fishing, birdwatching, and picnicking at Lake Shaftsbury State Park and Woodford State Park. They can also visit art galleries, museums, and historic sites. Special events are also hosted throughout Bennington in the summer for vacationers to enjoy.

What can visitors find in downtown Bennington?

Downtown Bennington offers charming shops, restaurants, and sidewalk cafés. Visitors can stroll along Main Street, browse through locally-owned shops, enjoy delicious meals at restaurants and cafés, and experience live theater performances and art galleries.

What are some nearby attractions to explore?

Visitors can explore Manchester for outlet shopping and picturesque scenery, visit the Vermont Country Store in Weston for a nostalgic shopping experience, or venture to Mount Equinox or hike the Appalachian Trail in the surrounding area. One of the best things Vermont is known for is Southern Vermont College, so stop by and take a look.

How long should visitors plan to stay in Bennington, VT?

It is recommended to plan for at least 2-3 days to fully explore the area.

Some popular bed and breakfast options in Bennington include the Henry House Inn, Four Chimneys Inn, and Knotty Pine Motel & Cabins.

How can visitors plan their visit to Bennington and the surrounding region?

Visitors can use the resources and travel guide provided by the Southwestern Vermont Chamber of Commerce, which promotes and advocates for businesses and organizations in the region.

How can visitors get to Bennington, VT?

Bennington is easily accessible by car from the Northeast region. The closest airport is Albany International Airport, approximately an hour's drive away.

What does Bennington, Vermont offer to visitors?

Bennington offers a unique blend of history, natural beauty, charming shops, and restaurants. Visitors can explore the town's downtown area, visit museums and attractions, and enjoy outdoor activities.

What is the Southwestern Vermont Chamber of Commerce?

The Southwestern Vermont Chamber of Commerce promotes and advocates for businesses and nonprofit organizations in the region. The Shires of Southwestern Vermont brand represents the diverse offerings and attractions in the area.

Where is Bennington located and how can visitors reach it?

Bennington is located in the southwest corner of Vermont, near the borders of New York and Massachusetts. Visitors can reach Bennington by car, bus, or train, with connections available from major cities in the area.

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