Nestled in its stunning natural surroundings, the Bennington area offers world-class cultural and artistic organizations, wide-ranging outdoor activities for all seasons, a variety of shopping opportunities, and rich local history.

Shops with a Character

Approx. 10 Min. Drive

Bennington Bookshop. Bennington’s independently owned bookstore. Wi-Fi. 109 South St, Bennington.

Bennington Potters. World-renowned handmade pottery, tableware, home accessories, furniture, and more. Owned and operated by Sheela Harden ’69. 324 County St, Bennington.

Bringing You Vermont. General store featuring local Vermont goods, and a café serving coffee, sandwiches, salads, and desserts. 434 Main St, Bennington.

Hawkins House. Handmade gifts and jewelry, clothing, and blown glass.  262 North St, Bennington.

Fiddlehead at Four Corners. Gift shop meets gallery. Owned and operated by Joel Lentzner ’91 and Nina Lentzner ’91. 338 Main St, Bennington. Temporarily Closed to foot traffic due to Covid. 

Approx. 30 Min. Drive

Manchester Designer Outlets. High-end shopping in an outdoor mall. 97 Depot St, Manchester Center.

Mountain Goat. Fine outdoor clothing and gear for serious adventurers and casual wanderers. 4886 Main St, Manchester Center.

Northshire Bookstore. Everything you want in a bookstore: great staff picks, regional books and products, and vinyl. 4869 Main St, Manchester Center.

H.N. Williams Store. General store with Vermont-made goods and a full deli. Family-owned and operated since 1840. 2732 VT-30, Dorset.

Approx. 1 Hr. Drive

Crossgates Mall. Eat, shop, and play at the Capital Region’s premier destination. 1 Crossgates Mall Rd, Albany, NY.

Colonie Center. Multi-level mall featuring retail shops, dining, and movie theater. 131 Colonie Center, Albany, NY.

Whatever you’re craving—a casual dinner or fine cuisine, homemade pastry or Japanese hibachi—food in the Bennington area is sure to satisfy.

Cafés & Bakeries

Approx. 10 Min. Drive

The Roasted Bean Espresso Bar. Quick, casual coffee spot. 336 North St, Bennington.

South Street Cafe. Coffee, tea, espresso, lunch, and dessert. Wi-Fi. 105 South St, Bennington. Temporarily closed due to Putnam Block Project.

Love a Bagel. Café and sandwich shop serving organic coffee. 704 Main St, Bennington.

The Loose Cannon Café. Café serving coffee, breakfast, and lunch with vegan, vegetarian, and gluten free options. 139 Main St, Bennington.

Avocado Pit. Casual lunch and dinner spot for fresh burritos, tacos, and salads. 201 South St, Bennington. 

Pubs & Cocktails

Approx. 15 Min. Walk

Kevin’s Sports Pub & Restaurant. Local sports bar serving lunch and dinner daily specials. A North Bennington favorite. 27 Main St, North Bennington.

Pangaea Lounge. Lounge serving cocktails, and a dinner menu hosting fresh local ingredients. 3 Prospect St, North Bennington.

Approx. 10 Min. Drive

Harvest Brewing. Craft beers, rotating art installations, and a warm environment. 201 South St, Bennington.

Madison Brewing. A microbrewery serving lunch and dinner. 428 Main St, Bennington.

The Tap House at Catamount Glass. Craft beverages, restaurant, and glass factory retail shop. 309 County St, Bennington.

The Miller’s Toll. Dinner club & cocktail lounge. 716 Main St, Bennington.

Village Garage Distillery. Distillery serving dinner. 107 Depot St, Bennington. 

Approx. 20 Min. Drive

Brown’s Brewing Company’s Walloomsac Taproom and Brewery. Artful old factory building on the river serving craft beer and a dinner menu with vegan, vegetarian, and gluten free options. Weekend lunch service. 50 Factory Hill Rd, North Hoosick, NY.

Casual Dining

Approx. 15 Min. Walk

Pangaea Lounge. Lounge serving cocktails, and a dinner menu hosting fresh local ingredients. 3 Prospect St, North Bennington.

Approx. 10 Min. Drive

Fuji Hibachi and Sushi. An assortment of Japanese cuisine that includes sushi, sashimi, bento, tempura, and hibachi grilled items. 132 Northside Dr, Bennington.

Publyk House. Vermont tavern style dining with gluten free options, and a spectacular view. 782 Hardwood Hill Rd, Bennington.

Blue Benn Diner. A 1945 Silk City classic serving New England breakfast, lunch and dinner diner staples. Named one of the “21 Best Diners in America” by Thrillist. Owned by John Getchell ’86. 314 North St, Bennington.

Bringing You Vermont. Café and general store serving coffee, sandwiches, salads, desserts and featuring local Vermont goods. 434 Main St, Bennington.

Your Belly’s Deli. Serving American deli food and sandwiches. 100 Pleasant St, Bennington.

Lucky Dragon. Casual dining, serving Chinese cuisine that offers a menu of lunch specials, dinner combinations and a buffet. A student favorite. 460 Main St, Bennington.

Papa Pete’s Diner. A local favorite serving traditional American breakfast and lunch dining staples. 1104 Woodford Rd, Woodford.

Fine Dining

Approx. 10 Min. Drive

The Grille at Mount Anthony Country Club. American fine dining. Lunch, dinner, weekend brunch, and a seasonal menu. 180 Country Club Rd, Bennington.

Allegro. Fine Italian dining. Serving dinner only. 520 Main St, Bennington.

421 Craft Bar and Kitchen. Fine Western dining. 421 Main St, Bennington

Quick & Delicious

Approx. 15 Min. Walk

Marigold Kitchen. A farm to table pizza restaurant with a BYOB atmosphere. Pizza made with organic flour, and locally sourced cheeses. 25 Main St, North Bennington.

Approx. 10 Min. Drive

Billy T’s Northside Dairy Bar at Bennington Lanes. Ice cream, burgers and more. 217 Northside Dr, Bennington.

Lil’ Britain. Authentic British restaurant serving fish and chips, bangers and mash, and other British lunch and dinner staples. 116 North St, Bennington.

Ramunto’s. Sports bar serving New York-style brick oven pizza, subs, and entrees. 519 Main St, Bennington.

Skiing & Snowboarding

Prospect Mountain. A cross-country ski center located in Woodford, VT, maintaining more than 18 miles of trails expertly groomed for both skating and classical cross-country skiing, as well as special snowshoeing and single-track trails. Prospect has a base lodge with a full restaurant. 204 Prospect Access Rd, Woodford.

Bromley Mountain. Voted first for family-friendly skiing, hosting 9 lifts and 47 trails on 148 skiable acres. 3984 VT-11, Peru. 

Jiminy Peak Mountain Resort. The only mountain resort in North America to generate its energy using wind power. Hosts 47 trails (21 night trails), and 9 lifts on 167.4 acres. 37 Corey Rd, Hancock, MA.

Mount Snow. Hosts 86 trails on 600 acres, serviced by 20 lifts. 89 Grand Summit Way, West Dover.

Stratton Mountain Ski Resort. 670 skiable acres of top-ranked terrain, 99 trails, and 11 lifts. 5 Village Lodge Rd, Stratton.

Golf

Mount Anthony Country Club. Voted one of the “Best Places to Play” by Golf Digest. 180 Country Club Dr, Bennington.

The Golf Club at Equinox. Named one of the “Top 75 courses in the U.S.” by Golf Digest and the “#1 Golf Course in Vermont” by Golfweek. 108 Union St, Manchester.

Hiking 

The Mile-Around-Woods. A 1.4-mile scenic road nearby the historic Park-McCullough House that features views of farmland, wildflowers, and undergrowth. Woods Ln, North Bennington.

Robert Frost Trail. Running from Lake Paran in North Bennington to the Robert Frost Stone House Museum in Shaftsbury, this 2-mile footpath offers views of deep woods, breathtaking waterways, and surrounding mountains. 121 VT-7A, Shaftsbury. 

The Long Trail continues the Appalachian Trail along the crest of the Green Mountain National Forest. Find the closest trailhead at Bald Mountain, accessible down Harbour Rd, Woodford.

Lakes, Rivers, and Outdoor Recreation

Lake Paran. Just five minutes from Bennington College, Paran Recreations is an environmentally conscious and locally run not-for-profit organization dedicated to helping people enjoy the beauty of nature and having healthy fun outdoors. They offer swimming with on duty lifeguards, canoe rentals, access to barbecue grills, a beach, concession stand, and much more. Opens Memorial Day weekend and closes after Labor Day weekend. Houghton Lane, North Bennington.

Woodford State Park. Just 20 minutes east of Bennington, this recreational park hosts a variety of amenities for the outdoor enthusiast. In addition to four cabins, the campground has 103 sites that includes 20 lean-tos, and an RV site. There is a small beach, picnic area, and several hiking trails. Rowboats, canoes, and kayaks are available for rent. Open Memorial Day Weekend through Columbus Day Weekend. 142 State Park Road, Bennington.

Big Big on the Battenkill Kayak and Tubing (BBBKT).  Just 30 minutes north of Bennington, BBBKT offers tubing, kayaking, and rafting down the Battenkill River. 5827 VT-313 Arlington, VT 05250.

Zoar Adventure Center.   Located just 30 minutes from Bennington, the center offers spring, summer and fall kayaking, stand-up paddle boarding and bike rentals. Guides available. Open May-October. 36 West Main St, Wilmington.

Approx. 10 Min. Drive

Bennington Battle Monument. Commemorating the Battle of Bennington, which occurred on August 16, 1777, and is considered to be the turning point in the Revolutionary War. 15 Monument Circle, Old Bennington.

The Old First Church. Pulitzer Prize for Poetry winner and Congressional Gold Medal recipient Robert Frost is buried in the cemetery at this historic church. Frost frequently wrote about settings from rural life in New England in the early twentieth century, using them to examine complex social and philosophical themes. 1 Monument Ave, Old Bennington.

Park-McCullough House. One of the finest and best-preserved Victorian mansions in New England. 1 Park St, North Bennington.

Robert Frost Stone House Museum. Robert Frost wrote “Stopping by the Woods on a Snowy Evening” at this historic property, which is maintained by Bennington College. Frost was a Pulitzer Prize for Poetry winner and a Congressional Gold Medal recipient. 121 VT-7A, Shaftsbury.

Approx. 30 Min. Drive

Hildene, The Lincoln Family Home. The former summer estate of Robert Todd and Mary Lincoln. 1005 Hildene Rd, Manchester.

Approx. 10 Min. Drive

Bennington Museum. The Bennington Museum features the Bennington Modernism Gallery with work included by former faculty members Pat Adams, Sir Anthony Caro, Paul Feeley, Jules Olitski, and Helen Frankenthaler ’49. 75 Main St, Bennington.

Bennington Cinemas. Seven-screen movie theater offering new releases. $5 matinees before 5 PM daily. 125 Phyllis Ln, Bennington. 

Oldcastle Theatre Company. Year-round professional theatre and acting classes. 331 Main St, Bennington.

Hathaway’s Drive-In Theater. A family tradition since 1948! Drive-in offering double features of new releases. 4762 NY-67, North Hoosick, NY.

Approx. 30 Min. Drive

Dorset Theatre Festival. Regional summer stock theatre at the Dorset Playhouse. Led by Artistic Director and Bennington College faculty member Dina Janis. 104 Cheney Rd, Dorset.

Williamstown Theatre Festival. Regional summer stock theatre on the campus of Williams College. 1000 Main St, Williamstown, MA.

Sterling and Francine Clark Art Institute. Boasts an extraordinary collection of Renaissance to late 19th century French Impressionist paintings. 225 South St, Williamstown, MA.

Massachusetts Museum of Contemporary Art (MASS MoCA). One of the largest centers for contemporary visual and performing arts in the country. The massive museum complex offers fine dining, gift shops, antiques, and a café. 1040 Mass MoCA Way, North Adams, MA.