Welcome to Bennington, Vermont! Nestled in the heart of Bennington County, this historic New England town is a captivating blend of rich history, vibrant arts, and stunning natural beauty. With a population of over 37,000, the county offers a quintessential Vermont experience, where the past and present intertwine on scenic backroads and bustling main streets. From the rolling Green Mountains to the charming Walloonscac River, Bennington’s unique atmosphere captivates every visitor.
The town itself, chartered in 1749, holds the distinction of being Vermont’s first. Its history is etched into its landscape, from the site of a pivotal Revolutionary War battle to the grand Victorian architecture that lines its streets.
Whether you’re a history buff, an art enthusiast, or an outdoor adventurer, Bennington offers an array of experiences that will leave you with lasting memories.
This guide is your key to unlocking the very best things to do in Bennington, with a curated list of 20 must-see attractions. Get ready to explore the hidden gems and popular spots that make this town a truly special destination.
Things to Do in Bennington, VT
1. Bennington Battle Monument
Bennington Battle Monument
Rising majestically above the town, the Bennington Battle Monument is an iconic symbol of American independence. This towering stone obelisk commemorates the Battle of Bennington, a crucial victory for the American forces in 1777 that played a significant role in the outcome of the Revolutionary War. The monument, standing at 306 feet, is one of the tallest obelisks in the world. Its sheer scale and historical significance make it a powerful landmark.
Visitors can take an elevator to the observation deck at the top of the monument. From this vantage point, you are treated to a breathtaking 360-degree view of the surrounding landscape, including the lush valleys of Vermont, Massachusetts, and New York. The site also features informational plaques detailing the history of the battle and the monument’s construction.
For the best experience, visit on a clear day to fully appreciate the panoramic views. The monument is part of a larger historic site, so take some time to walk the grounds and soak in the history. It’s a fantastic spot for photographers and anyone interested in American history.
Address: 15 Monument Cir, Bennington, VT 05201
2. Mount Anthony Country Club
For those seeking a bit of leisure and recreation, theMount Anthony Country Club offers a beautiful and challenging golf course with stunning views of the surrounding mountains. Established in 1897, it is one of the oldest country clubs in Vermont and is known for its scenic and well-maintained 18-hole course.
Beyond golf, the club offers a full-service restaurant and bar that is open to the public. It’s a great spot for a meal or a drink, offering a relaxed and elegant atmosphere. The views from the clubhouse are particularly beautiful at sunset.
You can often find opportunities to play as a non-member, but it’s a good idea to call ahead to inquire about tee times and any special events. The course can be a bit challenging, but it’s a rewarding experience for golfers of all skill levels.
Address: 180 Country Club Dr, Bennington, VT 05201
3. Old First Church
Standing proudly in the historic district of Old Bennington, the Old First Church is a masterpiece of colonial architecture and a site of profound historical importance. Built in 1805, this elegant white church is the oldest church building in Vermont and is listed on the National Register of Historic Places. The church’s simple yet majestic design, with its soaring steeple, is a classic example of New England meetinghouse architecture.
The churchyard is a key part of its historical appeal, serving as the final resting place for many notable figures, including five Vermont governors and the revolutionary war hero General John Stark. It is also the burial site of the famous poet Robert Frost, whose grave is marked with a simple stone bearing the inscription, “I had a lover’s quarrel with the world.”
The church is open to visitors for tours during the summer months. Walking through the quiet grounds and admiring the well-preserved gravestones is a somber but beautiful experience. The church’s setting, overlooking the scenic landscape, makes it a serene and reflective spot.
Address: 60 Monument Ave, Bennington, VT 05201
4. Robert Frost Stone House Museum
Just a short drive from Bennington, in the town of Shaftsbury, lies theRobert Frost Stone House Museum, the first home owned by the celebrated American poet. It was here that Frost lived with his family from 1920 to 1929 and wrote some of his most famous poems, including “Stopping by Woods on a Snowy Evening” and “New Hampshire.” The small, rustic stone house is a testament to his simple life and deep connection to the New England landscape.
The museum provides a compelling look into Frost’s life and work through guided tours and exhibits. You can wander through the rooms where he lived and wrote, seeing original furnishings and personal items. The surrounding grounds, with their meadows and woods, are as picturesque as the poetry they inspired.
To fully appreciate the experience, consider taking a guided tour to hear the stories behind the house and Frost’s creative process. The museum is a must-visit for literature lovers and anyone seeking a peaceful, inspiring retreat. Be sure to check their hours before you go, as they are seasonal.
Address: 121 Historic Route 7A, Shaftsbury, VT 05262
5. Park-McCullough Historic House
Stepping into thePark-McCullough Historic House is like a journey back in time to the Gilded Age. Located in North Bennington, this magnificent 35-room Victorian mansion was built in 1864 and is one of the best-preserved examples of its kind in the United States. The house was home to two prominent families, the Parks and the McCulloughs, and showcases a remarkable collection of original furnishings, artwork, and personal artifacts.
The architectural details are stunning, from the ornate woodwork to the grand staircase and decorative ceilings. The tour guides, often volunteers with a deep passion for the house’s history, bring the stories of the families and their servants to life with engaging anecdotes. The house also features a carriage barn and a children’s playhouse.
The Park-McCullough House hosts a variety of events throughout the year, including concerts, lectures, and festivals. Check their schedule for special programming, which often includes themed tours or seasonal celebrations. It’s a fantastic spot for a picnic on the expansive lawns.
Address: 1 Park Street, North Bennington, VT 05257
6. Covered Bridges of Bennington County
Bennington County is a scenic wonderland, and its charm is perfectly encapsulated in its historic covered bridges. These picturesque structures, often referred to as “kissing bridges,” are a hallmark of the Vermont landscape. In Bennington and the surrounding area, you can find a collection of these beautiful bridges, each with its own unique character and story.
The three most famous are the Paper Mill Village Bridge, the Silk Road Covered Bridge, and the Burt Henry Covered Bridge. They all cross the Walloomsac River and are located within a short driving distance of each other. The bridges offer fantastic photo opportunities, especially in the autumn when the foliage is at its peak.
Take a leisurely drive to visit all three. The Burt Henry Covered Bridge is particularly popular, with a small park and field nearby that is perfect for a picnic. The bridges are a testament to 19th-century engineering and are listed on the National Register of Historic Places.
Address: Silk Road Covered Bridge, Silk Rd, Bennington, VT 05201
7. Bennington Potters
For a taste of local craftsmanship and a perfect souvenir, a visit toBennington Potters is a must. This legendary pottery studio has been a staple of the Bennington community since 1948, creating handcrafted stoneware that is as functional as it is beautiful. Their distinctive glazes and classic designs have made their pieces beloved by generations.
The factory store, located at the Potters Yard, is a sprawling space filled with a wide variety of their classic and new designs. You can browse through an extensive collection of mugs, bowls, plates, and unique serving pieces. There’s also a “seconds” section where you can find slight imperfections at a discount, which can be a great way to find a bargain.
While there are no public tours of the pottery-making process, the store itself is a wonderful experience. Look for limited-edition designs or seasonal collections that make for a special gift. It’s a great place to pick up a truly local, handmade piece of Vermont.
Address: 324 County Street, Bennington, VT 05201
8. The Chocolate Barn
Prepare to indulge your sweet tooth atThe Chocolate Barn, a delightful hidden gem located just outside of Bennington in Shaftsbury. Housed in a charming red barn, this family-run shop is a paradise for chocolate lovers. They specialize in handmade chocolates, fudge, and an incredible array of other confections.
Beyond the chocolate, The Chocolate Barn also serves up delicious homemade ice cream, perfect for a treat on a warm day. The atmosphere is cozy and welcoming, with the rustic charm of the barn adding to the experience. It’s the kind of place that feels like it’s straight out of a storybook.
It can get busy, especially on weekends and holidays, so be prepared for a small line. However, the delicious treats are well worth the wait. The Chocolate Barn is a perfect stop to satisfy a craving or to pick up some unique gifts to bring home.
Address: 5055 Route 7A, Shaftsbury, VT 05262
9. Powers Market
For a taste of old-fashioned New England charm, visitPowers Market in North Bennington. This classic country store has been a community hub for nearly two centuries, serving as a one-stop shop for groceries, local goods, and delicious deli sandwiches. It’s a place where locals gather, and visitors feel instantly at home.
The market offers a great selection of Vermont-made products, including maple syrup, cheeses, and craft beers. It’s the perfect spot to assemble a picnic lunch before heading out to explore the area’s natural beauty. Their deli counter is known for its fresh, made-to-order sandwiches.
This is a great place to get a true feel for the local culture. Strike up a conversation with the friendly staff or other customers to get some insider tips on what to see and do in the area.
Address: 9 Main Street, North Bennington, VT 05257
10. Bennington Museum
Bennington Museum
The Bennington Museum is a treasure trove of Vermont’s rich history, art, and culture. It is perhaps most famous for being home to the largest public collection of works by Anna Mary Robertson Moses, better known as Grandma Moses. Her vibrant and charming folk art provides a unique glimpse into rural life in the 20th century. The museum’s extensive collection also includes Gilded Age furniture, Bennington pottery, and decorative arts.
Beyond the art, the museum features fascinating exhibits on Vermont’s military history, from the Revolutionary War to the Civil War. There are also galleries dedicated to the region’s industrial past, including the story of the once-thriving Bennington Pottery industry. The museum’s rotating exhibits ensure there’s always something new to discover.
An insider tip: The museum’s grounds are beautifully maintained and include a sculpture garden and the one-room Schoolhouse where Grandma Moses received her early education. The museum also hosts various events and workshops throughout the year, so be sure to check their calendar before your visit.
Address: 75 Main Street, Bennington, VT 05201
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11. North Bennington Outdoor Sculpture Show (NBOSS)
Art comes to life in a spectacular way at theNorth Bennington Outdoor Sculpture Show (NBOSS). This annual, free exhibition transforms the village of North Bennington into an open-air art gallery, with large-scale sculptures placed throughout the streets, parks, and fields. The show features works from local and regional artists, creating a dynamic and engaging experience.
The sculptures are often integrated into the landscape in surprising and thought-provoking ways. You can wander at your own pace, discovering new pieces around every corner. It’s a fun and interactive way to experience contemporary art in a unique setting.
The show typically runs from late spring through the fall. It’s a self-guided tour, so you can pick up a map at a local business or download one online. It’s a perfect activity for a leisurely walk or bike ride and a fantastic way to support the local arts scene.
Address: 48 Main St, North Bennington, VT 05257
12. The Bennington Bookshop
Book lovers will feel right at home atThe Bennington Bookshop, one of the oldest independent bookstores in Vermont. Established in 1928, this charming shop is a haven for bibliophiles, with its creaking wooden floors and shelves packed with a carefully curated selection of books.
The store specializes in new releases, but also features a fantastic collection of local interest books, children’s literature, and classic titles. The staff is knowledgeable and passionate about books, always ready to offer a recommendation or a bit of literary conversation.
This is the perfect place to find a new book to read by the fire or a unique gift. It embodies the cozy, intellectual spirit of New England.
Address: 109 South St, Bennington, VT 05201
13. Bennington Farmers’ Market
For a taste of fresh, local Vermont produce and goods, theBennington Farmers’ Market is an essential stop. Held on Saturday mornings, the market is a lively community event that brings together local farmers, artisans, and food producers.
You’ll find an abundance of fresh fruits and vegetables, delicious baked goods, artisanal cheeses, and farm-fresh meats. The market is also a great place to find unique handcrafted items, from jewelry to pottery. It’s a vibrant and friendly atmosphere, where you can chat with the people who grow and make the food you’re buying.
The market is seasonal, so be sure to check their schedule before you go. It’s a wonderful way to support the local economy and sample the best of what the region has to offer.
Address: 150 Depot St, Bennington, VT 05201
14. Hemmings Auto Museum
If you have a love for classic cars and automotive history, theHemmings Auto Museum is a must-see. Located in Bennington, this museum is a tribute to the passion and craftsmanship of classic cars. It’s home to a rotating collection of stunning vehicles, from vintage muscle cars to sleek roadsters.
The museum is run byHemmings Motor News, a well-known name in the classic car community. The collection is meticulously maintained and beautifully displayed, with detailed information about each vehicle’s history and significance. It’s a journey through the evolution of automotive design and technology.
The museum is a great spot for car enthusiasts of all ages. It’s a small but impressive collection that is easy to navigate. Be sure to visit their gift shop, which is packed with automotive memorabilia and books.
Address: 216 Main St, Bennington, VT 05201
15. The Walloomsac River Walk
For a peaceful stroll or a morning jog, theWalloomsac River Walk is a local favorite. This paved trail runs alongside the scenic Walloomsac River, offering beautiful views of the water and the surrounding natural landscape. The trail is flat and accessible, making it suitable for all ages and abilities.
The River Walk is a perfect place to enjoy some fresh air and connect with nature. You can watch the river flow, listen to the sounds of birds, and simply relax in a serene environment. There are benches along the way, perfect for a moment of quiet contemplation.
The trail is also the site of the Bennington Farmers’ Market, so you can combine your visit with a trip to the market on a Saturday morning. It’s a simple, yet rewarding, activity that showcases Bennington’s natural beauty.
Address: 150 Depot St, Bennington, VT 05201
16. The Dorset Playhouse
Just a short drive from Bennington, theDorset Playhouse is a true hidden gem for theater lovers. This charming regional theater, founded in 1929, has a rich history of producing high-quality professional theater during the summer months.
The Playhouse is housed in a beautifully restored barn, and its intimate setting ensures that there’s not a bad seat in the house. The productions often feature professional actors, and the quality of the performances is consistently excellent. It’s a wonderful way to experience live theater in a unique and historic setting.
Check their schedule in advance and book your tickets, as shows can sell out quickly, especially on weekends. Making a night of it with dinner in Dorset before or after the show is a great way to experience this picturesque town.
Address: 104 Cheney Rd, Dorset, VT 05251
17. The Carriage House at the Four Chimneys Inn
For a luxurious and rejuvenating experience, theCarriage House at the Four Chimneys Inn offers a boutique day spa in a stunning historic setting. Located in a beautifully renovated carriage house on the grounds of the elegant Four Chimneys Inn, this spa provides a tranquil escape.
The spa offers a range of services, from relaxing massages and facials to manicures and pedicures. The atmosphere is peaceful and serene, with professional and friendly staff dedicated to providing a personalized and pampering experience.
Treat yourself to a massage after a day of exploring, or book a couples’ treatment for a romantic afternoon. Reservations are highly recommended, especially on weekends, to ensure you can secure your desired time.
Address: 21 West Rd, Bennington, VT 05201
18. Hildene, The Lincoln Family Home
A perfect day trip from Bennington is a visit to Hildene, the magnificent summer home of Robert Todd Lincoln, the only surviving child of President Abraham Lincoln. Located in Manchester, Vermont, this Georgian Revival mansion is set on a sprawling 412-acre estate with breathtaking views of the Battenkill Valley.
The house itself is filled with Lincoln family artifacts, including some of President Lincoln’s personal items. The grounds are equally impressive, featuring a restored Pullman car, beautiful formal gardens, and a goat dairy. You can explore a network of walking trails and a floating boardwalk that winds through a wetland preserve.
Give yourself at least half a day to fully explore the house and grounds. The history is fascinating, and the scenery is simply spectacular. It’s a must-visit for anyone interested in American history or beautiful landscapes.
Address: 1005 Hildene Rd, Manchester, VT 05255
19. Bennington Center for the Arts
The Bennington Center for the Arts is a cultural hub that celebrates the arts and history of the American West and Vermont. The center houses a variety of galleries, including the American Artists of the West Gallery and the New England Gallery.
The center’s most unique feature is the Vermont Covered Bridge Museum, located within the building. This museum showcases the history and engineering of Vermont’s iconic covered bridges through a fascinating collection of photographs, models, and artifacts.
While the center’s main building is currently closed to the public, there are still events and exhibits that take place on the grounds. Check their website for current information and to see what might be open during your visit.
Address: 44 Gypsy Ln, Bennington, VT 05201
20. The Grille at the Mount Anthony Country Club
For a taste of fine dining with a view,The Grille at the Mount Anthony Country Club is a fantastic option. Overlooking the golf course and the scenic Vermont landscape, the restaurant offers a refined and elegant dining experience.
The menu features a variety of American classics and contemporary dishes, with a focus on fresh, local ingredients. The atmosphere is relaxed yet sophisticated, making it perfect for a special occasion or a nice dinner out. The views from the dining room are particularly spectacular at sunset.
Reservations are recommended, especially on weekends, to ensure you get a table. The Grille is a great way to enjoy a delicious meal in a beautiful setting.
Address: 180 Country Club Dr, Bennington, VT 05201
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Conclusion
Bennington, Vermont, is a destination that captivates with its timeless charm and a remarkable blend of history, culture, and natural beauty. From the soaring heights of the Bennington Battle Monument to the serene tranquility of the Robert Frost Stone House, this town offers a journey through both American history and the soul of New England. Its vibrant arts scene, embodied in the Bennington Museum and the North Bennington Outdoor Sculpture Show, provides endless opportunities for discovery and inspiration.
Whether you’re exploring the historic covered bridges, indulging in local treats at The Chocolate Barn, or simply enjoying the peaceful atmosphere of the River Walk, Bennington promises an experience that is both enriching and unforgettable. It’s a place where every corner holds a story and every landscape is a work of art.
So pack your bags and set off on your own adventure to Bennington. Discover its cobblestone streets, friendly locals, and a charm that will stay with you long after you’ve left. Come and create your own cherished memories in this truly special Vermont town.
