Things to Do in Bennington, VT

The inn sits in the heart of Old Bennington, one of New England’s best-preserved colonial villages. The monument, the cemetery, the church — most of it is within a five-minute walk.

• Bennington Battle Monument
  The most visited historic site in Vermont and a short walk from the inn. Take the elevator to the top for sweeping views of three states.
• Old First Church
  Vermont’s oldest church and the burial site of Robert Frost, just steps from the inn. Attend Sunday service for the full experience.
• Bennington Centre Cemetery
  Designated “Vermont’s Sacred Acre,” beside Old First Church, it holds the graves of Robert Frost, three governors, and Revolutionary War soldiers.
• Bennington Museum
  A quarter-mile walk from the inn, with art, Vermont history, and the world’s largest public collection of Grandma Moses paintings.
• Old Bennington Walking Tour
  A self-guided tour of Old Bennington’s colonial village, passing 27 historic sites along Monument Avenue, steps from the inn.

Southern Vermont is known for scenic drives, with mountain byways, village roads, and covered bridges that are especially beautiful in foliage season.

• Vermont Covered Bridges
  Five covered bridges in Bennington County, including three clustered along the Walloomsac River — the Silk Road, Paper Mill Village, and Henry bridges.
• Molly Stark Byway
  Route 9 between Bennington and Brattleboro is one of Vermont’s most celebrated scenic drives, especially spectacular in peak foliage season.
• Route 7A / Route 100 Loop
  A classic 93-mile southern Vermont loop through Shaftsbury, Arlington, Manchester, and the mountain villages beyond — ideal for a full foliage day.
• Mount Equinox Skyline Drive
  A classic foliage outing on historic Route 7A, this paved toll road climbs 5.2 miles to sweeping summit views between Arlington and Manchester.

In winter, people come here for a classic Vermont getaway. You have well-known ski resorts within reach, and also the quieter side of the season: snowy trails, horse-drawn sleigh rides, and small-town winter charm.

• Downhill Skiing
  Twelve ski resorts within an hour of the inn. Bromley Mountain is about 30 minutes away; Mount Snow about 40; Stratton Mountain about 50.
• Willow Park Sledding
  Bennington’s best sledding hill, free and open to the public, with plowed parking. A quick drive from the inn at 275 Park Street.
• Lake Paran Ice Skating
  When conditions allow, volunteers clear a skating area on this 35-acre lake, about 10 minutes from the inn. Check the Lake Paran Facebook page for conditions.
• Lively’s Livery
  Carriage, wagon, and sleigh rides about 10 minutes from the inn, available for private occasions and seasonal outings. Call (802) 447-7612.
• Prospect Mountain Nordic Center
  Cross-country skiing and snowshoeing on Route 9 East in Woodford, about 15 minutes from the inn. Rentals available; moonlit skiing on select Saturdays.
• Vermont Mountain Adventures
  Guided snowmobile tours through the Green Mountain National Forest, about 25 minutes from the inn in Manchester. All experience levels welcome.
• Taylor Farm Sleigh Rides
  Horse-drawn sleigh rides in Londonderry, about 45 minutes away, with a fireside stop for hot cider and marshmallows.
• Hildene, The Lincoln Family Home
  Cross-country skiing and snowshoeing on the Lincoln estate grounds, about 24 miles away. Rentals are available on site.

From a legendary Silk City diner car to family-run brewpubs and farm-to-table kitchens, Bennington’s dining scene punches well above its size. Ask the innkeepers what’s new.

• Elm Street Market
  Bennington’s best deli, voted three years running. Boar’s Head sandwiches, soups, and salads. About a mile away.
• Madison Brewing Co.
  A family-run brewpub on Main Street with housemade beers, hearty food, and a welcoming local atmosphere.
• The Publyk House
  A casual neighborhood restaurant on Route 7A, open daily for dinner, about 4 miles from the inn.
• Pangaea Restaurant
  A well-regarded farm-to-table restaurant about 5 miles away, known for locally sourced menus.
• Powers Market and Deli
  A beloved country store in the village of North Bennington serving breakfast and lunch. Worth the short drive.
• Kevin’s Sports Pub & Restaurant
  A decades-old North Bennington favorite, known for half-pound burgers and award-winning chili.
• Blue Benn Diner
  A Silk City diner car open since 1948, ranked #13 among America’s most classic diners. Tabletop jukeboxes and all.
• The Grille at Mt. Anthony Country Club
  Dinner with sweeping Green Mountain views, about a mile from the inn. A local favorite for a relaxed evening out.
• Ramunto’s Brick Oven Pizza
  A casual Main Street pizzeria with New York-style brick oven pies and 23 beers on tap. About a mile from the inn.
• Benner’s Bagels Pizza N’ Whatnosh
  A family-owned Main Street spot for pizza, calzones, and bagels. Breakfast through dinner, seven days a week.
• Village Garage Distillery
  A craft distillery on Depot Street pouring bourbon, rye, vodka, gin, and cocktails, with a barbecue kitchen inside.
• Harvest Brew
  A nano-brewery and beer parlor on South Street, open evenings. No meals — just good beer in a relaxed setting.

Sugarhouses, organic farm stands, alpaca farms, and a year-round farmers market make it easy to eat and shop locally.

• Bennington Farmers Market
  A lively seasonal market featuring local produce, artisan goods, and Vermont makers. Moves indoors November through April.
• Apple Barn and Country Bake Shop
  Pies, cider donuts, u-pick berries, and a wide selection of Vermont products, about 5 minutes south on Route 7. Open seasonally.
• Armstrong Farm
  A family-operated farm about 5 miles south, selling pure Vermont maple syrup, fresh vegetables, gourds, jams, and honey — a quintessential local stop in season.
• Shaftsbury Alpacas
  A friendly alpaca farm about 5 miles from the inn with a small shop of hats, sweaters, and scarves. Pairs well with a visit to Park McCullough and Mile-Around Woods.
• Clear Brook Farm
  A beloved organic farm stand in Shaftsbury, about 7 miles from the inn,  open May through October, with vegetables, meats, cheeses, and picnic supplies.
• Glastenview Maple Farm
  A family-run sugarhouse in Shaftsbury, about 15 minutes away, with year-round tours and tastings of maple syrup including infused varieties like bourbon and cinnamon.
• Merck Forest and Farmland Center
  A free, open-daily conservation farm in Rupert, about 30 minutes away, with organic maple syrup, 3,000 taps, and hiking trails.
• Billings Farm and Museum
  A working farm and museum in Woodstock celebrating Vermont’s rural heritage. Makes for a beautiful scenic day trip, about 2.5 hours away

From easy wildflower walks behind the Bennington Museum to the challenging Appalachian Trail climb up Harmon Hill, the area has trails for every pace and every season.

• Aiken Wildflower Trail
  A quiet nature trail directly behind the Bennington Museum, just a quarter mile from the inn.
• Bennington Area Trail System (BATS)
  A network of multi-use trails for hiking, running, and mountain biking on Mount Anthony.
• Harmon Hill
  A challenging 3.4-mile out-and-back on the Appalachian Trail, about 5 miles from the inn on Route 9.
• Robert Frost Stone House hiking loop to Lake Paran
  A well-marked loop to Lake Paran begins at the Frost Stone House, about 7 miles from the inn.
• Lake Paran
  A quiet 35-acre lake, about ten minutes away, with swimming, boating, fishing, and easy kayak access.
• Mile-Around Woods at Park McCullough
  A bucolic trail network on the Park McCullough estate in North Bennington, about 10 minutes away.
• Woodford State Park
  Swimming, hiking, paddle boats, and kayaking on a scenic elevated reservoir about 15 minutes from the inn.
• Prospect Mountain Nordic Center
  Cross-country skiing and snowshoeing in winter; hiking and trail access in other seasons. About 15 minutes away.
• Lake Shaftsbury State Park
  A pretty lake with a beach, canoe and kayak rentals, and a shoreline nature trail, about 20 minutes away.
• Clark Art Institute trails
  Free hiking trails through meadows and woodland surrounding the Clark, about 12 miles away.
• Hildene walking trails
  Walking trails wind through peony gardens, a working farm, and open fields, about 24 miles away.
• Robert Frost Interpretive Trail
  A worthwhile literary day trip with an easy 1.2-mile trail and posted Robert Frost poems, about 80 miles away.

Some rides here lead up to lookout views across three states and three mountain ranges, while others wind through wooded preserves where you might spot deer, turkey, or foxes along the way. In winter, the countryside feels especially storybook, with horse-drawn sleigh rides, wool blankets, hot cider, and a fire waiting in the woods.

• Lively’s Livery
  Trail rides and carriage, wagon, and sleigh rides about 10 minutes from the inn. Call (802) 447-7612.
• Rhythm Hollow Stables
  Horseback riding and lessons in North Bennington, about 10 minutes from the inn.
• Kimberly Farms
  Horseback riding with panoramic views in nearby Shaftsbury, about 15 minutes from the inn.
• Taylor Farm Sleigh Rides
  Classic horse-drawn sleigh rides in Londonderry, about 45 minutes away, with marshmallow roasts and barn tours.
• Mountain View Ranch
  Trail rides through beautiful Green Mountain scenery in Danby, about 45 minutes away.

Bennington has long been a good place to browse independently owned shops, galleries, and maker-led businesses.

• Bennington Museum Gift Shop
  A quarter mile from the inn, with Vermont artisan work, gifts, and one-of-a-kind finds.
• Fiddlehead at Four Corners
  An artisan marketplace on Main Street, about 5 minutes from the inn.
• Hawkins House
  A craft marketplace on North Street featuring Vermont artisans, about 5 minutes away.
• Bennington Bookshop
  Vermont’s oldest independent bookshop, established in 1928 — local authors, gifts, and a strong children’s section.
• Tony Conner Gallery
  Original Vermont landscape paintings by an award-winning artist, available by appointment in Bennington.
• Village Chocolate Shoppe
  Homemade chocolates, fudge, truffles, and gelato on Main Street — a sweet stop in any season.
• Katie Cleaver Metalsmith Jewelry
  One-of-a-kind handcrafted jewelry, made on site in her Main Street shop since 1975.
• Catbird Studio
  An art and gift shop now located in Manchester Village, about 25 minutes from the inn.
• Apple Barn and Country Bake Shop
  Baked goods, u-pick berries, and a selection of Vermont products, about 5 minutes south. Open seasonally.
• Shaftsbury Alpacas
  Alpaca hats, sweaters, and scarves from a friendly farm about 5 miles from the inn.
• Manchester Designer Outlets
  Major designer outlet shopping about 25 miles away in Manchester.

Some guests come for Revolutionary history, others for Grandma Moses, Robert Frost, or a museum afternoon in the Berkshires. This list includes places near the inn and a few farther away that are still easy to enjoy in a day.

• Bennington Museum
  A standout museum with Vermont history and the world’s largest public collection of Grandma Moses paintings.
• Monument Arts & Cultural Center
  Formerly the Bennington Center for the Arts, with galleries, a theater, and the Covered Bridge Museum.
• Bennington Battle Monument
  A short walk to the most visited historic site in Vermont. Take the elevator to the top for views of three states.
• Old First Church
  Vermont’s oldest church and the burial site of Robert Frost, tied to the earliest history of Bennington.
• Dollhouse and Toy Museum of Vermont
  A charming small museum with dollhouses, vintage toys, and nostalgic displays, about 5 minutes from the inn.
• Park McCullough Historic Estate & Gardens
  A beautifully preserved Victorian governor’s mansion on 200 acres in North Bennington, about 10 minutes away.
• North Bennington Outdoor Sculpture Show (NBOSS)
  Free outdoor sculpture exhibition displayed in North Bennington village, June through November each year.
• Robert Frost Stone House Museum
  A literary landmark about 7 miles away where Frost wrote “Stopping by Woods on a Snowy Evening” in the 1920s.
• Bennington Battlefield State Historic Site
  The actual site of the 1777 Battle of Bennington, about 10 miles away across the New York border.
• American Museum of Fly Fishing
  The world’s largest collection of angling artifacts and history, about 25 minutes away in Manchester.
• Clark Art Institute
  A major art destination with an exceptional permanent collection and walking trails, about 12 miles away.
• MASS MoCA
  One of the most notable contemporary art museums in the Northeast, about 16 miles away in North Adams.
• Southern Vermont Arts Center
  Galleries, sculpture park, and performances on a historic estate, about 20 miles away in Manchester.
• Hildene, The Lincoln Family Home
  Robert Todd Lincoln’s estate with tours, gardens, and a restored Pullman car, about 24 miles away.
• Historic Deerfield
  A meticulously preserved 18th-century Massachusetts village with guided tours, about 50 minutes away.

This corner of New England has been a serious destination for live performance since the 1930s — Tanglewood, Jacob’s Pillow, and the Williamstown Theatre Festival draw audiences from across the country every summer. The venues closer to the inn draw the same caliber of talent, in rooms that seat a few hundred people.

• Sonatina School of Music
  A short walk from the inn — in summer, free public student concerts bring live piano to Old Bennington.
• Oldcastle Theatre Company
  Professional theater about a mile from the inn, producing New York-caliber performances throughout the season.
• Bennington Theater
  Touring comedians, musicians, plays, and musicals on an intimate 136-seat stage, about a mile from the inn.
• Monument Arts & Cultural Center
  A 315-seat theater about 2 miles from the inn, with a full season of professional musicals, live music, and concerts.
• Williamstown Theatre Festival
  A prestigious summer theater festival in Williamstown, Massachusetts, about 10 miles from the inn.
• Hubbard Hall
  A community-centered venue for opera, dance, theater, and performing arts, about 18 miles from the inn.
• Dorset Theatre Festival
  A well-known regional theater destination worth the drive for an evening out, about 35 minutes away.
• Weston Theater Company
  A beloved Vermont theater company in the village of Weston, about 45 minutes away.
• Jacob’s Pillow
  America’s longest-running international dance festival, about 50 minutes away in the Berkshires.
• Tanglewood
  Summer home of the Boston Symphony Orchestra in Lenox, Massachusetts, about 50 minutes away.

For many guests, the best time to visit Bennington is when something seasonal is happening downtown or nearby.

• Vermont Maple Open House Weekend
  Sugarhouses across Bennington County open every March for tours, tastings, sugar-on-snow, and a true taste of Vermont’s sweetest season.
• Bennington Battle Day Weekend
  Vermont’s longest-running civic celebration every August 16th weekend, with a parade, cannon fire, and Revolutionary War reenactors at the monument steps.
• Garlic Town, USA!
  A Labor Day Weekend tradition drawing thousands to downtown Bennington with 130+ vendors, live music, chef demos, and a designated Vermont Signature Event.
• Bennington Quilt Fest & Harvest Fest
  Two beloved fall events in September and October celebrating Vermont’s quilting tradition and harvest season with vendors, live music, and peak foliage.
• Thursday Night Live
  A summer concert series bringing live music and Hemmings classic car cruise-ins to downtown Bennington on Thursday evenings throughout the season.
• Winterfest in North Bennington
  A mid-winter community celebration in January or February with live music, craft vendors, food, and the annual Lake Paran Plunge.

Whether you’re here to keep up a fitness routine or slow down with a massage, Bennington has options.

• Golf at Mount Anthony Country Club
  Vermont’s first golf course and a Golf Digest Best Places to Play, just two minutes from the inn.
• Willow Park Pickleball Courts
  Two pickleball courts are located at the public park at 275 Park Street, open dawn to dusk on a first-come basis.
• Bennington Tennis Center
  An indoor tennis bubble on Lovers Lane, open to the public, about 5 minutes from the inn.
  
• Bennington Recreation Center
  A public indoor swimming pool and fitness center on Gage Street, about 5 minutes from the inn.
• Anytime Fitness
  A half mile from the inn — the most convenient option for guests who want to keep up their gym routine.
• The Yoga Place
  A welcoming studio 5 minutes from the inn offering classes in multiple yoga styles for all levels.
• Revolution Racquet & Fitness Club
  A gym 5 minutes away with cardio, weights, racquetball, and fitness classes. Inn guests receive a $5/day rate.
• Zumba with Andrea
  Drop-in Zumba classes at The Mill on Benmont, about 5 minutes from the inn. Call (802) 379-5468.
• Starr Luxe Day Spa
  A day spa about 5 minutes from the inn offering massage, facials, and beauty treatments.
• Massage For You
  Affordable therapeutic massage in North Bennington, well-regarded by locals and returning guests alike.