One Of Vermont's Oldest Towns Is An Artsy Escape With A Walkable Downtown Full Of Shops And Charm

With its iconic rolling hills, covered bridges, and vibrant foliage, Vermont offers visitors countless opportunities to enjoy the outdoors, indulge in culinary delights, and experience New England charm. Among the top activities for a Vermont fall getaway are hiking through fiery-colored trails, visiting historic towns, and exploring art and culture. While mountain-circled Burlington is Vermont's largest city, the biggest town in Southern Vermont is Bennington, a New England gem speckled with covered bridges, wildflowers, and vintage shops.

Bennington has long been a source of inspiration for artists and writers. Shirley Jackson wrote her classic short story "The Lottery" while living in Bennington. Donna Tartt studied at Bennington College, which inspired her novel "The Secret History." A painting by the renowned artist Grandma Moses named "Bennington" captures the town's grey stone architecture. But Bennington's culture isn't just a thing of nostalgia: Today, Bennington's arts scene thrives with free concerts, theater performances, and an annual sculpture show that adds contemporary flair to this historic town.

What makes Bennington so special? Perhaps it's the perfect mix of natural beauty, rich history, and modern culture. From its serene lake and wildflower trails to its Revolutionary War ties, Bennington offers amazing recreational and historical activities in addition to its versatile cultural events. Add in opportunities for picking your own blueberries or hunting for antiques, and it's clear why this charming Vermont town continues to captivate visitors.

The story of Bennington begins with the indigenous Abenaki and Mohican tribes, who originally inhabited the area. European settlers arrived in the 18th century, and in 1749, Bennington became the first town chartered in what is now Vermont. It played a pivotal role in American history during the Revolutionary War, serving as the site of the Battle of Bennington in 1777. American forces killed over 200 British soldiers, and the victory weakened British forces and led to Gen. John Burgoyne's surrender at Saratoga. Today, the towering 306-foot Bennington Battle Monument commemorates this historic event.

Bennington is filled with reminders of its history. The Henry House is a shining example — and one of the oldest. It was built in 1769 and was home to the family of Revolutionary War leader and local politician Lt. William Henry, and the house boasts colonial decor and mountain views from the porch. Live out your colonial Vermont fantasies by renting out this historic building on Airbnb. The house overlooks the Henry Covered Bridge, Bennington's oldest covered bridge, dating back to 1840. Driving over it will feel like being transported to the 1800s. Meanwhile, the Old First Church of Bennington in the middle of Bennington's historical district was Vermont's first church, built in 1805, and is listed on the National Register of Historic Places.

At the Bennington Museum, history and culture intertwine. Housed in a building dating back to the 1850s, the museum holds the largest collection of Grandma Moses paintings, artifacts from the Battle of Bennington, and modernist works by local artists. During the summer, the museum hosts free Friday evening concerts in its courtyard. If you visit Bennington between June and November, be sure to check out the impressive North Bennington Outdoor Sculpture Show.

Bennington's walkable downtown is evidence of the town's thriving arts scene. The Bennington Theater offers a mix of dramatic performances and fun events. For handmade treasures, stop by Hawkins House, where you'll find pottery and hand-crafted jewelry from local artisans. Antiquing enthusiasts will be thrilled to know that Bennington was named one of the 10 best antique towns in New England by NewEngland.com. While Chester is usually named Vermont's "antique capital," Bennington holds its own with spots like Main Street Antiques and Covered Bridge Antiques.

Bennington has a variety of satisfying restaurant options, too. The Grille serves up a New England-inspired menu with patio views of the Green Mountains. For a romantic setting, head to Pangaea, where a worldly menu features everything from quesadillas to short ribs. The Blue Benn Diner is top-rated on Tripadvisor, offering a vegetarian-friendly menu in a 1950s rail car. And beer lovers won't want to miss Madison Brewing Company, a brewpub offering seasonal and year-round brews, live music, and hearty lunch and dinner options.

Outdoor enthusiasts will also find plenty to love in Bennington. The George Aiken Wildflower Trail, located near the Bennington Museum, is a short but scenic 0.3-mile walk that showcases native plants. For a longer trek, take the 2-mile Robert Frost Trail, named after the New England poet who lived in Bennington and whose grave rests at the Old Bennington Cemetery. The trail passes through red pine trees planted by Frost himself, as well as remnants of Frost's orchard. The trail's loop ends at Lake Paran, where you can kayak, fish, or take a dip in the waters. Exploring the underrated town of Bennington, you might find yourself taking the road less traveled — a choice that, as Frost once wrote, could make all the difference.