35 Things To Do in Bennington

Nestled in the scenic embrace of Vermont, Bennington is a charming town that offers every visitor an array of activities. This vibrant destination boasts history, culture, and natural beauty, making it an ideal spot for travelers to explore.

What makes Bennington so captivating? The blend of historic sites, picturesque landscapes, and lively local events offers something for everyone. From sampling local flavors to wandering through quaint streets, Bennington is a place where adventure awaits around every corner.

Bennington Battle Monument

Our Rating: 8.7/10

The Bennington Battle Monument is a striking landmark rising 306 feet above the charming town of Bennington. Visitors can enjoy a scenic elevator ride to the top, where breathtaking panoramic views of the Green Mountains and surrounding states await.

Inside the monument, visitors will discover a small museum offering insight into the history of the Battle of Bennington. A gift shop provides unique souvenirs, ensuring visitors leave with a memory of their journey. The monument hosts special events supported by a dedicated volunteer group, making it a lively and engaging destination for history buffs and casual travelers.

Bennington Museum

Our Rating: 9.1/10

Bennington Museum beckons visitors with its decadent array of art and history. Nestled in a charming stone building that once served as a church, it boasts over 40,000 artifacts showcasing southern Vermont’s culture. Art lovers are drawn to the extensive collection of American folk art, including the world’s largest public display of Grandma Moses paintings.

Visitors can wander through exhibits that capture Vermont’s vibrant history and artistic heritage. The museum invites exploration through its diverse galleries, featuring everything from historic photographs to contemporary crafts. As you stroll, each piece tells a story, offering a vivid glimpse into the past and present of this picturesque region.

Park-McCullough Historic House

Our Rating: 8.6/10

The Park-McCullough Historic House is a gem in North Bennington. Its Victorian architecture and lush gardens provide a picturesque setting. Visitors can stroll through the vibrant gardens, which offer a peaceful escape year-round.

Events fill the mansion’s calendar, especially during holidays. Guests can join in festive activities like wreath-making and caroling. The Carriage Barn hosts these events, creating a warm, inviting atmosphere. The house’s grandeur and rich history make it a must-visit. Whether exploring the grounds or attending an event, the Park-McCullough House promises a memorable experience.

The Coffee Bar

Our Rating: 8.5/10

The Coffee Bar is a must-visit spot for coffee lovers and social seekers. Known for its rich and full-bodied blends, it invites guests to savor a peaceful moment. Alongside your cup, try the popular apple fritter for a delightful treat.

This cozy place is more than just a coffee shop. It offers a lively blend of music, art, and community. Regular live music performances allow visitors to enjoy a vibrant atmosphere while unwinding with a drink. Whether you prefer a quiet corner with a book or the buzz of conversation, The Coffee Bar provides a warm and inviting experience.

Bennington Theater

Our Rating: 8.5/10

Bennington Theater is a vibrant hub for arts and community. Nestled in downtown, this charming venue offers a blend of live performances that captivate audiences. From classic plays to new productions, there’s always something worth seeing.

Visitors can enjoy an intimate setting where the powerful stories on stage connect deeply with the audience. The theater’s dedication to celebrating diverse art forms makes it a cultural gem in town. Attendees can often find themselves exploring thought-provoking art exhibitions alongside theatrical performances. Beyond the shows, the theater creates a space for community engagement, making it more than just a place to watch plays.

Apple Barn and Country Bake Shop

Our Rating: 8.7/10

The Apple Barn and Country Bake Shop invites everyone to explore its charm. Visitors can dive into a world filled with homemade treats and Vermont’s finest products. The rich aroma of baked goods greets you, promising flavors that captivate the senses.

Beyond the delectable delights, the barn offers a slice of Vermont’s rustic beauty. Families can wander to the new covered bridge, offering a perfect spot for snapshots and strolls. For those with a sweet tooth, their signature maple ice cream is a must-try, delivering a taste of local sweetness. The Apple Barn is a delightful must-visit.

Bennington Plaza

Our Rating: 7.8/10

Bennington Plaza is a lively spot. It’s a perfect place for visitors who love shopping and dining. With a variety of shops, there’s something for everyone. From unique boutiques to charming cafes, Bennington Plaza offers a delightful experience.

Stroll through the area and enjoy the vibrant atmosphere. Don’t miss the chance to explore its culinary gems, where you can savor delicious local dishes. Whether looking for a unique gift or just window shopping, this plaza offers a charming experience.

Oldcastle Theatre Company

Our Rating: 8.5/10

Oldcastle Theatre Company stands as a beacon for art lovers. Since its opening in 1972, this not-for-profit company has been a staple of professional theatre in the area. Audiences can delight in the intimate setting where local talents perform classic and contemporary plays.

Visitors are treated to various shows, from drama to light-hearted musicals. The theatre’s cabaret performances, like “Moonlight in Vermont,” transform an evening into an enchanting experience with songs that capture the region’s spirit. Whether a night out with friends or a particular date, the theatre promises an unforgettable cultural journey.

Four Chimneys Inn & Restaurant

Our Rating: 8.7/10

The Four Chimneys Inn offers a cozy and inviting stay. Visitors are charmed by its elegant rooms and historic ambiance. The lush gardens provide a tranquil retreat for guests to unwind and soak in the Vermont scenery. It’s a great spot to enjoy a leisurely afternoon or a romantic evening walk.

The Four Chimneys Restaurant brings a delightful touch of French-Vermont cuisine to create a memorable dining experience. The fine dining options cater to diverse palates, making it an ideal spot for food lovers. Whether it’s a special occasion or a casual dinner, guests can savor exquisite flavors and impeccable service.

The Publyk House

Our Rating: 8.5/10

The Publyk House is a charming dining spot nestled in a building with a unique history. Once an old horse barn, it offers a cozy atmosphere with fireside dining and a deck with stunning views. It’s a perfect place to unwind and enjoy Vermont’s rustic charm.

Visitors can savor various dishes, from juicy steaks to fresh seafood. The restaurant also features a bountiful salad bar, appealing to those looking for lighter fare. With a full bar offering creative cocktails, there’s something to complement every meal. The Publyk House is an inviting venue for events and parties. Friendly service and a welcoming vibe create a memorable dining experience.

Fiddlehead at Four Corners

Our Rating: 8.7/10

Fiddlehead at Four Corners is a vibrant hub of creativity. Visitors can wander through this eclectic gallery, housed in a historic marble bank, and discover an array of contemporary crafts and fine art.

From delicate blown glass to striking pottery, the collection showcases the incredible skill of North American artists. Jewelry, woodwork, and textiles fill the space with color and texture. Each piece tells a story, inviting art lovers to explore and appreciate the diverse displayed talents.

Willow Park

Our Rating: 8.5/10

Willow Park, nestled in the northwest corner of Bennington, is a favorite spot for locals and visitors. The park offers expansive green spaces perfect for a leisurely afternoon picnic or a game of frisbee. Kids can delight in the play areas with swings and slides. There’s space for jogging or walking, offering a peaceful escape from daily life.

During winter, the park transforms with sledding opportunities, making it a lively destination regardless of the season. Whether seeking adventure or relaxation, Willow Park has something for everyone.

Vermont Veterans Home Deer Park

Our Rating: 8.5/10

Vermont Veterans Home Deer Park offers a serene escape. It honors veterans while providing a peaceful spot for visitors. Nestled within the Veterans Home property, the park features walking paths where guests can enjoy a stroll surrounded by nature’s beauty.

The park is for more than just walking. It includes a public picnic area with spacious lawns and shade trees perfect for a relaxing afternoon. Visitors can bring lunch, grab a table, and enjoy a meal in the quiet outdoors. Watching the deer roam nearby can be a delightful experience for children and adults alike.

Old First Congregational Church

Our Rating: 8.5/10

Old First Congregational Church is a must-visit for lovers of history and architecture. This stunning church, built in 1805, showcases classic Federal period design. Visitors can admire its elegant facade and step inside to see the beautiful interior, which features original woodwork and remarkable stained glass windows.

The church isn’t just about architecture; it offers a glimpse into Vermont’s early days. This place was key to early settlers’ spiritual and social life. Behind the church lies the Bennington Center Cemetery, where you can explore the graves of notable figures, including American poet Robert Frost.

Bennington Farmers’ Market

Our Rating: 8.5/10

Bennington Farmers’ Market is a lively spot buzzing with activity. It’s more than just a market—it’s a community hub where locals and visitors unite. The market overflows with fresh produce from local farms, offering everything from crisp apples to colorful squashes.

Visitors can explore stalls filled with homemade bread, artisanal cheese, and sweet treats crafted by local bakers. Sampling these delicious foods is a must-do. Live music often fills the air, providing a pleasant backdrop as people shop and socialize. Unique crafts and handmade goods are also available, adding a special touch to the shopping experience.

Bennington Cinemas

Our Rating: 8.3/10

Bennington Cinemas offers a cozy spot for movie lovers looking to catch the latest films. It’s one of the town’s favorite hangouts located on Phyllis Lane. With several screens, moviegoers can choose from various genres, making it perfect for a family outing or a date night.

Visitors often enjoy the comfortable seating and good sound quality that enhances the viewing experience. Snacks like popcorn and candy add to the charm, giving that classic cinema feel. Whether you’re a fan of blockbusters or indie films, Bennington Cinemas promises an enjoyable escape from daily life with its fresh lineup of movies.

Madison Brewing Co.

Our Rating: 8.7/10

Madison Brewing Co. is a delightful gem. Nestled on Main Street, this cozy brewpub offers a warm and inviting atmosphere. Visitors can enjoy a variety of fresh beers crafted with care, exploring a mix of New England IPAs and classic Old-world styles.

The pub’s lively ambiance makes it a perfect spot for locals and tourists. It’s not just about the beer; the menu is a treat, too. From hearty pub favorites to delicious starters, there’s something for every palate. Whether you’re a beer enthusiast or simply looking for a great place to unwind, Madison Brewing Co. promises a memorable experience.

Silk Road Covered Bridge

Our Rating: 8.5/10

The Silk Road Covered Bridge is a charming piece of history from 1840, lovingly preserving the traditional Town lattice truss design. Visitors can step back in time as they cross this quaint bridge, taking in the picturesque view over the Walloomsac River.

Photography enthusiasts will enjoy capturing the stunning scenery around the bridge, especially during the vibrant fall foliage. The surrounding area is perfect for a leisurely walk or a peaceful picnic by the riverbank, offering a serene escape into nature. Nearby are two other covered bridges, making it a delightful experience for those who wish to explore the history and charm of Vermont’s iconic structures.

Harvest Brewing

Our Rating: 9.0/10

In the heart of downtown Bennington, Harvest Brewing is a charming nano brewery that captivates visitors with its small-batch ales and inviting atmosphere. The brewery offers a vegetarian-centric menu, featuring dishes like the Rattlesnake Burrito and House Nachos, which pair perfectly with its craft beers.

Beyond its culinary delights, Harvest Brewing provides a cozy setting adorned with pinball machines, arcade games, and board games, ensuring entertainment for all ages. Live music performances on Saturday nights add to the vibrant ambiance, making it a must-visit spot for locals and travelers seeking a memorable experience.

The Yoga Place

Our Rating: 8.5/10

The Yoga Place offers a peaceful escape for body and mind. Guests can explore a variety of yoga styles, from Kripalu to Vinyasa, tailored for all levels. The environment, described as nurturing by visitors, ensures everyone feels welcome.

In addition to regular classes, The Yoga Place hosts special workshops that promise a deeper dive into wellness. There’s always something new and intriguing to try. Whether it’s Yoga Nidra or Pilates, visitors can immerse themselves in joyful practices that promote well-being. Stop by 532 Main St. for a session and experience the calm only dedicated yoga enthusiasts can provide.

Hawkins House Craftsmarket

Our Rating: 9.0/10

Hawkins House Craftsmarket is a delightful haven for art and craft enthusiasts. This historic shop is brimming with handcrafted treasures, from shimmering jewelry and intricate pottery to vibrant textiles and unique woodwork. Each piece tells a story, often crafted by local Vermont artisans, making every item a true collectible. The cozy ambiance, combined with the charm of its rustic displays, invites visitors to explore, discover, and be inspired.

What makes Hawkins House truly special is its commitment to showcasing artistry while offering a warm, welcoming experience. Whether you’re searching for the perfect gift, a personal keepsake, or simply a slice of Vermont’s creative spirit, this gem delivers. Strolling through its thoughtfully curated displays feels like a journey through a gallery of craftsmanship, with each corner sparking wonder and admiration.

Blue Benn

Our Rating: 8.4/10

Blue Benn is a delightful retro diner nestled in Bennington. It invites guests to take a cozy seat and enjoy the warm atmosphere. This beloved spot is famous for its homemade donuts that locals genuinely cherish.

Visitors can savor a hearty breakfast or a juicy burger for lunch. The vibrant decor adds to the dining experience, making each visit memorable. Blue Benn offers a small but cherished classic American diner culture time capsule.

421 Craft Bar and Kitchen

Our Rating: 8.3/10

The 421 Craft Bar and Kitchen offers delightful flavors and experiences. It’s a go-to spot for locals and visitors looking to enjoy creative cocktails and tasty dishes. The menu features mouth-watering choices like Maple Mustard wings and Linguine with meatballs. The vibrant setting makes it a perfect place to unwind after exploring the town.

Whether dining with friends or going solo, the lively atmosphere and friendly staff make it an unforgettable stop. Be ready for a bustling environment on Saturdays, as word about their incredible food and drinks has spread far and wide.

Hampton Inn Bennington

Our Rating: 8.0/10

The Hampton Inn Bennington offers a cozy and welcoming atmosphere for travelers. Nestled close to the lush Green Mountains, it provides stunning views and easy access to outdoor adventures. Guests can enjoy hiking trails and scenic drives right from the hotel. This hotel is minutes away from Bennington’s vibrant downtown. Visitors can easily explore local shops, quaint cafes, and cultural spots.

In winter, the Hampton Inn’s proximity to ski resorts makes it a perfect base for skiing enthusiasts looking to hit the slopes. The hotel’s convenient location also places guests near Manchester’s outlet stores for some retail therapy. With its warm, inviting ambiance and excellent location, this hotel is an ideal starting point for any Bennington adventure.

Carving Studio and Sculpture Center

Our Rating: 8.5/10

Nestled in the charming landscape of West Rutland, the Carving Studio and Sculpture Center offers a distinctive experience. Visitors can enjoy an inspiring environment filled with artistic energy. Here, the legacy of the Vermont Marble Company comes alive, providing a unique backdrop for creativity.

The studio hosts intriguing sculpture education programs where participants can learn the art of carving. With inactive quarries nearby, it is an ideal spot for seasoned artists and curious novices. These programs invite you to explore the depths of artistic expression amidst the raw beauty of Vermont’s marble-rich terrain.

The Dutchman’s Tavern

Our Rating: 8.3/10

The Dutchman’s Tavern is a vibrant spot nestled in downtown Bennington. Known for its welcoming atmosphere, it invites locals and visitors alike to enjoy its diverse offerings. With 25 draft beers on tap, there’s plenty for brew enthusiasts to explore. Sip on a cold one while soaking in the lively setting.

Outdoor seating options make this a perfect venue for enjoying sunny afternoons. The tavern regularly hosts events like the popular Paint & Sip sessions. Participants can unleash their creativity while indulging in their favorite drinks. It’s an engaging way to spend an afternoon or evening making new friends or enjoying time with old ones.

Gamers Grotto

Our Rating: 8.5/10

The Gamer’s Grotto is a haven for card games, board games, and miniatures enthusiasts. Visitors can dive into their favorite games or discover new ones.

The vibrant shelves include classic video games and nostalgic DVDs. Guests can enjoy board game nights, where laughter and strategy fill the air. Whether a casual player or a competitive gamer, there’s something for everyone.

Bennington Free Library

Our Rating: 8.5/10

The Bennington Free Library is more than just a place to read. It invites visitors into a world filled with history and discovery. The Vermont History Room is a treat for those curious about the past. It showcases unique local items that reveal fascinating stories about the region. There’s always something new to explore, from historical documents to rare finds.

Families will love the children’s section, where engaging books and activities inspire young minds. Storytimes and special events often light up this area, creating a joyful atmosphere for kids and parents alike. Whether diving into a new book or exploring local history, the library offers something special for everyone.

Main Street Antiques

Our Rating: 8.5/10

Main Street Antiques is a charming destination offering a delightful journey through time. Located at 473 Main Street, this shop offers vintage and antique items, perfect for collectors and curious visitors. Stepping inside, visitors are greeted by a captivating array of items, each with its own story and history.

The selection is rich and varied, from intricate jewelry to classic furniture pieces. It’s easy to spend hours exploring the unique finds. Perfect for a leisurely afternoon, this spot promises adventure at every turn. Whether you’re hunting for a specific piece or simply browsing, Main Street Antiques is sure to enchant and inspire.

Bennington Recreation Center

Our Rating: 8.4/10

The Bennington Recreation Center is a lively hub for both relaxation and fitness. Families flock here to enjoy the public swimming pool. Swimmers of all skill levels can splash around or swim laps. The center also boasts a well-equipped weight room. It invites fitness enthusiasts to break a sweat. With modern gear, it’s an excellent spot for both beginners and seasoned athletes.

A sauna offers a warm escape. Visitors can unwind after a workout or spend time in the comforting heat. Whether you’re looking to stay active or relax, the Bennington Recreation Center has something for everyone to enjoy.

Ramunto’s Brick Oven Pizza

Our Rating: 8.5/10

Ramunto’s Brick Oven Pizza offers a delicious break for any traveler. It’s the perfect spot to enjoy classic brick oven pizzas on Main Street. Visitors can savor various pizza options, complemented by a good selection of beers.

Whether you’re grabbing a slice to fuel your day or winding down with a meal, this pizzeria promises a satisfying experience. Fans of the cozy atmosphere will enjoy their meal with friends or family while taking in the vibrant local scene.

Sunny Side Diner

Our Rating: 8.5/10

Sunny Side Diner offers an inviting experience for breakfast and lunch enthusiasts. Located on VT-9, this charming diner is known for its warm atmosphere and friendly staff. Visitors can indulge in homemade meals, from classic pancakes to hearty biscuits and gravy. Each dish is crafted with care, making every bite unforgettable.

The down-home setting adds to the diner’s appeal, providing a cozy spot to enjoy a morning feast. Whether you’re looking for a satisfying plate of corned beef hash or a delightful cinnamon roll, Sunny Side Diner promises a comforting start to your day in Bennington.

Glastenbury Wilderness

Our Rating: 8.8/10

Glastenbury Wilderness offers a thrilling escape into nature’s embrace. This remote and stunning area is perfect for adventure seekers. Hikers can explore the Bald Mountain Trail, which winds through dense forests. The trail offers a challenging but rewarding journey, with breathtaking views from the summit waiting to mesmerize every visitor.

For those who love the great outdoors, the White Rocks Overlook is a must-visit. The panoramic vista of Bennington from here is nothing short of spectacular. Trails are well-marked, making it easy for beginners and seasoned hikers to enjoy. The area is also famous for its colorful legends and mysterious history, adding an intriguing touch to any visit.

Grandma Moses Schoolhouse Museum

Our Rating: 8.5/10

The Grandma Moses Schoolhouse Museum offers a charming glimpse into the world of the beloved folk artist. Visitors can explore the schoolhouse Anna Mary Robertson Moses, known as Grandma Moses, attended as a child. Inside, the walls are adorned with reprints of her well-known paintings, showcasing scenes of rural American life. Guests can imagine the past as they explore interactive exhibits.

The museum provides a unique opportunity to learn about the cultural history that inspired Grandma Moses. It is a tribute and an educational space, ideal for art lovers and history buffs. Step into a piece of history and feel the inspiration that sparked a legendary artist’s journey.

Bennington Welcome Center

Our Rating: 8.5/10

The Bennington Welcome Center is a gateway to Vermont’s charm and beauty. Located at the interchange of Routes 279 and 7, it offers visitors a warm entrance to the region. This well-maintained spot greets guests with free Wi-Fi and complimentary coffee, creating a welcoming atmosphere.

Travelers can find helpful information about local attractions and events. From museums to nature trails, the staff suggests all types of adventures. They are always ready to help plan your trip around the picturesque towns and landscapes.

Bennington is brimming with unique experiences and cultural gems that promise to enrich every visit. Whether you’re soaking up history, exploring local art, or enjoying the natural beauty, this town offers an array of unforgettable activities for travelers of all tastes.