Bennington is one of the oldest and most picturesque towns in New England. Home to Vermont’s most visited historic monument, the Bennington Battle Monument testifies to the colonial history of this town. Other top things to do in Bennington Vermont include visiting Bennington Museum, Bennington Potters and Bennington College. The Bennington Vermont restaurants are also a treat thanks to foodies who appreciate local craft beer and good locally-grown food.
Bennington Vermont
Bennington is the largest town in southwestern Vermont. There are three parts to Bennington: Old Bennington, Downtown Bennington and North Bennington VT.
Located in Bennington County, Bennington was set up in 1749 by New Hampshire’s Royal Governor, Benning Wentworth. The first settlers didn’t arrive until 1761 though. Settling in what is now Old Bennington, the first settlers came from Worcester and Amherst in Massachusetts and religious separatists from Connecticut.
Thanks to its geographical location, Bennington Vermont was caught in a tussle between New York and New Hampshire even while the first settlers were from Massachusetts.
During the American Revolution, the Battle of Bennington in 1777 was an important victory for the American side. Technically the battle took place in what is now New York but both sides were fighting over an arms depot located in Bennington itself.
During the 19th century, Bennington was an important manufacturing center, primarily for the famous Bennington Pottery and timber processing. Downtown Bennington expanded in the 19th century.
North Bennington is a village in the northwest part of the town of Bennington. The grounds of Bennington College lies in both Bennington and North Bennington.
Things to do in Bennington VT
If you are looking for things to do, Bennington VT has a lot to offer for a small town in Vermont from the fantastic Bennington Museum to the many outdoor sports available in the nearby Green Mountains.
Apple Barn and Country Bake Shop
The Apple Barn and Bakery is open seasonally from May through October. They have pick-your-own strawberries and blueberries from mid-June through mid-August. There are over 300 acres of orchard with over a dozen varieties of apples available. With all those apples, expect amazing apple cider donuts and delicious baked goods.
Address: 604 Route 7 South, Bennington
Bennington Museum
Bennington Museum is an eclectic collection of art and history from both of Vermont and New England. Visiting the small but well-curated Bennington Museum is one of the best things to do in Bennington Vermont. The gift shop is also a great place to buy souvenirs.
Among the treasures on display, there are rooms of 19th century Bennington Pottery. There is also the largest collection of Anna Mary Robertson “Grandma” Moses’s work. Grandma Moses is known for American folk art depicting the life and times of the 1900s. It wouldn’t be Bennington without a display of items from the Battle of Bennington as well. You can also appreciate one of the oldest American flags in existence.
The Bennington Museum has a large collection of Grandma Moses painting.
Outside the museum, lies 6 acres of the Hadwen Woods which has the George Aikin Wildflower Trail, as well as a children’s play area. The charming 1/3 mile wildflower trail is filled with the wildflowers that George Aiken, former Governor of Vermont and horticulturalist, loved. On a summer day, the George Aiken Wildflower Trail is one of the most beautiful places in Bennington.
Address: 75 Main Street
The George Aiken Wildflower Trail is one of the prettiest walks you can take in Bennington VT.
Bennington Battle Monument
Completed in 1891 in connection with Vermont’s centennial celebrations, the Bennington Battle Monument is Vermont’s most visited historic site.
This impressive monument commemorates the famous Battle of Bennington of 1777. At 306 ft. tall, the blue-grey limestone tower is an imposing presence in the landscape. From the observation deck, you can see three different states. Don’t worry, there’s an elevator that goes up to the observation deck.
Throughout the year, there are historical events and reenactments taking place, including a reading of the Declaration of Independence on the Fourth of July. There is a Battle of Bennington re-enactment every August as well.
In 2022, the Battle of Bennington re-enactment is scheduled for the weekend of August 14 and 15. On the Saturday, there is also an annual 5K race and on the Sunday, a historical walking tour of the historic buildings of Old Bennington.
Address: 15 Monument Circle
Things to do in Bennington include seeing the countryside from the top of the Bennington Battle Monument.
Bennington Potters
For over 70 years, Bennington Potters have created quality stoneware in Vermont. Take a tour through their iconic workshop and learn all the ins and outs of the ceramics world. Bennington Potters Yard has more than 5,000 sq. feet of retail space as well.
Bennington Potters was built on the site of an older pottery, the Norton Factory established in 1793. By the end of the 19th century, the Norton Factory was the biggest pottery in the USA having brought in artisans from Staffordshire England which was known for its pottery.
Unlike the Norton Factory, Bennington Potters has more of a mid-century modern aesthetic.
There is an old mill and schoolhouse on the premises dating back to the 1920’s. Note that Bennington Potters also have a second location in Burlington Vermont.
Address: 324 County Street
Bennington College
Widely regarded as having one of the most beautiful college campuses in the Northeast, Bennington College is a small private liberal arts college. Notable alumni include Betty Ford (former First Lady), authors Brett Easton Ellis and Donna Tartt and actors, Justin Theroux and Peter Dinklage.
The Robert Frost Stone House Museum is located on the grounds of Bennington College. The poet resided in the house from 1920-1929 during which he wrote many of his most famous poems. Frost had helped with the founding of Bennington College in the 1930’s. The Robert Frost house is technically in nearby Shaftsbury.
Address: 121 Historic Route 7A Shaftsbury
Bennington Farmers’ Market
A year-round market, the Bennington Farmer’s Market is held on Tuesdays and Saturdays. The market is indoors in the winter and outdoors in the summer. You can find the usual range of farmers’ market goods – fresh produce, baked goods, dairy products, fresh eggs and other locally produced goods.
Address: 100 Veterans’ Memorial Drive (Summer); 650 Main St (Winter)
Covered Bridges
Among the cool things to do in Bennington VT, is check out its three covered bridges that cross the Walloomsac River connecting Bennington to North Bennington. Located within 2 miles of each other are three of Bennington County’s five covered bridges: the Burt Henry Covered Bridge, the Paper Mill Village Bridge and the Silk Road Covered Bridge.
The Covered Bridge Museum, created as a replica of the nearby Burt Henry Covered Bridge, was established in 2003 to explain the history and importance of covered bridges in Vermont. Unfortunately, the museum is now closed due to funding issues. Although currently part of a lawsuit, hopefully the Museum recovers from its woes and opens again soon.
The Covered Bridge Museum in Bennington Vermont would be fascinating if it were open again.
Dollhouse and Toy Museum of Vermont
Love miniatures? You will be charmed by the Dollhouse and Toy Museum of Vermont. Among the displays are dollhouses, dollhouse rooms, miniature art, and character dolls of famous people like Elvis and Thomas Jefferson.
It is open only on Saturday and Sunday afternoons.
Address: 212 Union Street
Hemmings Vintage Vehicle Display
The Hemmings Vintage Vehicle Display is a collector car display of old cars and trucks, including a 1929 popcorn truck, a 1924 fire truck, and a 1940 Buick convertible. Along with the cars, there are vintage signs and other accessories on display. The display is free to enter and open seasonally from June through October.
Address: 216 Main St
Long Trail/Appalachian Trail
The 272 Long Trail is a challenging route popular with backpackers and campers. It also has 166 miles of side trails.
Built. between 1910 and 1930, the Long Trail is he oldest long distance hiking trail in the USA and the inspiration for the more-famous Appalachian Trail. In fact, the Appalachian Trail and the Long Trail overlap for about 100 miles in Southern Vermont. The Long Trail stretches from the Massachusetts-Vermont border until the Canadian border.
Harmon Hill Trail is a 3.3. mile hike that is part of the Long Trail near Bennington VT. Considered a challenging route, the trail starts with a steep ascent. The reward at the top is stunning views over Bennington and the countryside.
Oldcastle Theatre Company
This professional theater company has been running since 1972. It was formed by a group of 5 actors from New York who created a touring company. They have been at their current address since 2012 and since 2020 own the building they use. In addition to plays, they run performing arts workshops and Shakespeare theater camp for kids.
Address: 331 Main Street
Old First Church
The Old First Church in Old Bennington was the first Protestant church established in Vermont. A central meeting place for early Bennington and colonial Vermont history, Old First Church was designated “Vermont’s Colonial Shrine” in 1935.
Address: 1 Monument Circle
The Old First Church in Bennington Vermont is one of the historic buildings in Bennington.
It’s hard to believe this dilapidated building once hosted two Founding Fathers.
Outdoor Sports
Bennington and the nearby area are great for lovers of outdoor sports. The natural beauty of the area is everywhere you look. You’ll see why Robert Frost and Norman Rockwell loved this part of the world.
For water lovers, there is swimming, fishing and boating at nearby Lake Paran, Woodford State Park and Lake Shaftsbury State Park.
Outdoor Secrets Unwrapped organise trout fishing trips in the Southern Green Mountains of Vermont. Randomly, Outdoor Secrets also do a hot sauce that will blow your socks off!
Hikers will find lots of different trails, such as the Robert Frost Trail, the Long Trail, the Lake Shaftsbury State Park Nature Trail and the Woodford State Park Nature Trail. These are only a small selection of the beautiful nature trail options available.
In winter, outdoor activities include ice fishing, ice skating, sledding, Nordic skiing, snowshoeing and snowmobiling. Nearby Alpine ski resorts include Killington Resort, Mount Snow, Stratton Resort and Okemo Mountain Resort.
Park-McCullough Historic Governor’s Mansion
The Park-McCullough Historic Governor’s Mansion is a 35 room Victorian mansion built in 1864-65. President Benjamin Harrison stayed at the house when he came to dedicate the Battle of Bennington Monument. It was family-owned until 1965. Now, it is a popular house history museum and wedding venue.
The Mile-Around Woods Hike is a 1 mile walking trail that starts behind the Park McCullough house and runs through the estate.
Address: 1 Park Street, North Bennington
The Park McCullough House in North Bennington VT is a historic estate.
Restaurants Bennington Vermont
Restaurants in Bennington Vermont are a diverse lot as befits an eclectic college crowd and foodie locals. You will find great restaurants that run the gamut from casual to fine dining.
Blue Benn Diner (314 North Street) is a traditional diner that has been a fixture among Bennington Vermont restaurants for generations. House in a 1940’s railroad car, this diner has been rated among the best diners in the country. Feed coins into the old fashioned jukebox to hear your favourite songs playing while tucking into your favourite comfort food.
The Blue Benn Diner, one of the best restaurants in Bennington Vermont.
The first brew pub in the area, Madison Brewing Company (428 Main Street) has been serving craft beer since 1990. They also serve a wide selection of food from sandwiches to hot meals and also have a kids’ menu.
The 421 Craft Bar and Kitchen (421 Main Street) offers farm to table tapas style food with craft beer, wine and specialty cocktails.
Pangea Restaurant (3 Prospect Street, North Bennington) offers farm to table fine dining in a casual setting. They serve BIPOC beer/wine from California and Oregon as well as craft beers.
Things To Do Bennington VT Festivals
As shown by these festivals, people in Bennington Vermont really appreciate local food and brew.
Homebrew Festivals
The Winter Homebrew Festival is an annual craft beer festival in Downtown Bennington occurring I March/April. Featuring 30 regional home brewers of beer, cider, wine and mead, there are also food vendors and craft vendors. The winter food theme is hearty warming food soups and stews.
Similar to the Winter Homebrew Festival, the Summer Homebrew Festival happens every August. In 2022, the Summer Homebrew Festival is scheduled for Saturday August 6.
Garlic and Herb Festival
The annual Garlic and Herb festival happens every Labor Day Weekend and is a celebration of all things garlic. A family-friendly festival, there are live bands, food vendors, craft vendors and a beer and wine garden.
Things To Do Near Bennington VT
Scenic drives like The Shires of Vermont Byway and the Molly Stark Byway are a great way to see some of the best places in Southern Vermont. Both the Shires of Vermont Byway and the Molly Stark Byway are an easy drive and you’ll pass by the surrounding towns and get your fill of country stores, too.
The Shires of Vermont Byway
The Shires of Vermont Byway is a scenic drive that goes from the Massachusetts border of Vermont in Pownal north to the town of Manchester. It is Route US7 from Pownal to Bennington and then Route US7A from Bennington to Manchester.
Running along 75 miles of road, you see the best of this historic and beautiful region. There are 5 covered bridges along the way too.
Visiting the historic Henry Covered Bridge is one of the things to do in Bennington
Molly Stark Byway
The Molly Stark Byway is named after the wife of the general that won the Battle of Bennington. She was a formidable figure and helped recruit men for the New Hampshire Militia which helped her husband win that historic battle. Along the Molly Stark Byway, you will also pass the Molly Stark State Park.
Also known as Route 9, this scenic road runs east-west for 4o miles. It connects Brattleboro Vermont with Bennington Vermont and goes through Wilmington and the Green Mountains. This scenic byway is especially beautiful in the Fall when the colors of the trees are ablaze.
Lake Shaftsbury State Park
Covering 84 acres, the main attraction of this state park is the small lake, Lake Shaftsbury, itself. There is a sandy beach and swimming in the lake. There’s a nature trail that goes around the lake. There are also lean-to sites for group camping and one cottage to rent.
Woodford State Park
Located in the Green Mountains, the 400 acre Woodford State Park is the Vermont state park at the highest elevation. The landscape is wetlands, open water and forest which attracts wildlife.
There is a beach area near Adams Reservoir. You can rent canoes and kayaks to paddle around the Reservoir. There are several hiking trails including one that goes around the Reservoir. There is a large campground with 103 campsites and 4 cabins.
In winter, the state park is popular for cross-country skiing, snowshoeing and snowmobiling.
Green Mountain Bluegrass and Roots
The Green Mountain Bluegrass and Roots music festival is held in nearby Manchester Vermont. It will run from Friday August 19 until Sunday August 21 in 2022.
Think Coachella of Americana music with a main stage and a dance tent. There are camping facilities as well as food and drink vendors.
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