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If you’ve been compiling your list of things to do in Bennington, VT, in the summer, you may already know the southwestern corner of the Green Mountain State is packed with naturally beautiful views, good food, and a lot to do and see. Bennington’s mix of college-town arts energy and relaxed country charm makes it an ideal warm-weather place to visit. Use this guide to map out an unforgettable summer in Bennington, VT, complete with the best sites, activities, and Bennington restaurants.
What to Do in Bennington, VT This Summer
Throw a Round at Willow Park Disc Golf Course
If you’re up for some disc golf, head to Willow Park disc golf course on East Road. The course weaves through open meadows and shady woods, so you’ll get to have fun while also taking in views of Mount Anthony. Brick tee pads, Prodigy baskets, and clear signage make Willow Park easy for first-timers, while the 6,000-foot length still gives seasoned players something to brag about.
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Check Out the Bennington Battle Monument
Standing at 306 feet, Vermont’s tallest structure happens to be right in Bennington. The Bennington Battle Monument commemorates the 1777 battle that paved the way to Saratoga and America’s independence. Be sure to ride the elevator to the observation deck for a three-state view! Interpretive panels at the monument site give a lot of insight into everything that unfolded in the fields below historically, so this is a great stop if you consider yourself a history buff.
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Explore American Art at the Bennington Museum
Ten minutes northwest of downtown, the Bennington Museum houses the world’s largest public collection of Grandma Moses paintings. You can also see other exhibits like nineteenth-century glassware and rotating contemporary exhibits that highlight New England modernists. A good indoor option when the summer heat rolls in, the museum is one of the best activities in Bennington if you prefer to stay out of the sun.
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Get in Touch with Nature at Molly Stark State Park
Named for the outspoken wife of General John Stark, Molly Stark State Park is a 148-acre sanctuary that lies just east of town on VT-9. A gentle 1.7-mile climb takes you to the top of Mount Olga, where you’ll find a retired fire tower that gives you 360-degree views. Shaded picnic tables, a tidy campground, and ranger-led programs are also key park attractions throughout the summer. Bring binoculars; warblers and other wildlife are always around if you enjoy getting a peek at nature.
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Visit the Robert Frost Stone House Museum
The 1769 farmhouse where Frost penned “Stopping by Woods on a Snowy Evening” is a must-visit near Bennington if you are a fan of the author’s work. Inside the Robert Frost Stone House Museum, draft manuscripts and his writing chair give you a small peek at the poet’s daily rituals, while recordings will allow you to hear Frost reciting his own lines. Weekend poetry workshops are even scheduled at different times of the year, and the museum is only open periodically through the summer, so be sure to check out the website before planning a visit.
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Hike the Equinox Skyline Trail in Manchester
Tackle the Equinox Skyline Trail in Manchester for a rewarding 6.2-mile hike up Mount Equinox. Starting off West Union Street, this moderate trail climbs through forests to the 3,848-foot summit, offering 360-degree views of the Green Mountains and Adirondacks. Perfect for fit beginners or seasoned hikers, the trail is open all day in the summer, and leashed dogs are welcome.
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Festivals and Events in Bennington and Surrounding Areas
Summer in Bennington, VT, always brings festivals and events. Therefore, chances are, if you are visiting in the summer, you can find something fun to do either in Bennington or nearby. A few annual events to look for include:
- North Bennington Outdoor Sculpture Show (mid-June–October)—Dozens of large-scale works transform village greens and walking paths into an open-air gallery.
- Vermont Garlic and Herb Festival (Labor Day Weekend) – Follow your nose to the fairgrounds for garlic ice cream, cooking demos with the prized main ingredient, and bluegrass jams.
- Battenkill Fly Fishing Festival (early June)—Clinics, gear demos, and friendly casting competitions on one of VT’s most treasured trout streams.
- Dead of Summer Music Festival in Manchester (July 11-13)—Three days of rock vibes with 20+ bands on two stages, onsite camping, craft vendors, yoga sessions, and a 21-plus beer garden at Hunter Park.
The Best Bennington Restaurants
After enjoying all the best activities in Bennington, you’re bound to have worked up an appetite. Luckily, Bennington’s dining scene covers cravings from diner-style comfort food to white-tablecloth places for more refined dining experiences. Below are a few crowd-pleasers locals and visitors tend to enjoy:
- Madison Brewing Co. – Family-owned brewpub pouring small-batch ales alongside the best burgers around.
- The Publyk House – A restored 18th-century barn serving steaks, maple-glazed salmon, and awesome views.
- Blue Benn Diner – Vintage rail-car diner famous for all-day breakfasts and house-baked pies.
- Pangaea Fine Dining – Contemporary Vermont cuisine made from seasonal farm produce and locally sourced ingredients.
- Lil’ Britain Fish & Chips – Authentic English pub classics right on North Street.
- The Village Chocolate Shoppe – Hand-dipped truffles, maple “moose pops,” and other yummy treats.
Enhance Your Summer in Bennington, VT with Silver Therapeutics
Ready to elevate the journey? Swing by Silver Therapeutics on Northside Drive for local insight and the finest flower, edibles, and concentrates in the state. Our team loves swapping trail tips and dinner recommendations almost as much as guiding you to the ideal strain. Browse the live menu online, order ahead for quick pickup if your schedule is packed, or drop in to shop.
