Where to Eat

Where to Eat, Sleep, Explore

Whether you’re visiting campus for the first time as a prospective student or planning a local adventure for your parents during family weekend, the town of Bennington is a gem of the Green Mountains.

Though located less than four hours from major cities like New York and Boston, Bennington’s abundant natural beauty, including rolling mountains with biking and hiking trails and close proximity to some of the best skiing in the East, feels worlds away.

Bennington offers critically-reviewed restaurants and eateries as well as farm-to-table produce and local specialties. The region offers antique finds and high-end designer shopping alongside traditional retail and grocery stores that can supply your daily needs.

Where to Eat

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 offering drive-thru and cafe. 336 North St, Bennington.

Brown Cow Café. Espresso, lattes, cappuccino, soups, sandwiches, and more. Serving Brattleboro-based Mocha Joe’s coffee. Owned and operated by Amy Blomquist Buckley ’83. 139 Main St, Bennington.

South Street Cafe. Coffee, tea, espresso, lunch, and dessert. Wi-Fi. 105 South St, Bennington.

Bakkerij Krijnen. Authentic Dutch bakery famous for its stroopwafels. Daily soups, breads, and European pastries. 1001 Main St, Bennington.

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

Pubs & Cocktails

Approx. 15 Min. Walk

Kevin’s. North Bennington’s favorite sports bar and restaurant. 27 Main St, North Bennington.

Pangaea Lounge. Informal setting for drinks and a bite to eat. 1 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.

Safford Mills Inn and Café. B&B, martinis, appetizers. The oldest house in Bennington Village, circa 1774. 722 Main St, Bennington.

Approx. 20 Min. Drive

Brown's Brewing Company's Walloomsac Taproom and Brewery. Artful old factory building on the river with excellent beer and food. 50 Factory Hill Rd, North Hoosick, NY.

Casual Dining

Approx. 15 Min. Walk

Pangaea Lounge. Lighter fare innovations and a full bar. Co-owned by Bill Scully ’94. 1 Prospect St, North Bennington.

Approx. 10 Min. Drive

Fuji Hibachi and Sushi. Japanese food. A popular new restaurant close to campus. 132 Northside Dr, Bennington.

Publyk House. Vermont dining with a spectacular view. 782 Hardwood Hill Rd, Bennington.

Blue Benn Diner. A 1945 Silk City classic serving New England diner staples. Named one of the “21 Best Diners in America” by Thrillist. 314 North St, Bennington.

Two Brews Cafe. Breakfast, crepes, sandwiches, vegan/vegetarian options. 230 North St, Bennington.

Bringing You Vermont. Restaurant and general store featuring local Vermont goods. 434 Main St, Bennington.

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

Lucky Dragon. Chinese food. One of the most popular places with students. 460 Main St, Bennington.

Papa Pete’s Diner. A local favorite for breakfast and lunch. 1104 Woodford Rd, Woodford.

Fine Dining

Approx. 15 Min. Walk

Pangaea. “A fine dining salve for those used to the flawless choices in Manhattan,” according to The New York Times. Co-owned by Bill Scully ’94. 1 Prospect St, North Bennington.

Approx. 10 Min. Drive

The Grille at Mount Anthony Country Club. American fine dining, seasonal menu. 180 Country Club Rd, Bennington.

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

Quick & Delicious

Approx. 15 Min. Walk

Powers Market. North Bennington’s oldest neighborhood deli. Wi-Fi. 9 Main St, North Bennington.

Marigold Kitchen. Pizzeria. 25 Main St, North Bennington.

Approx. 10 Min. Drive

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

Lil’ Britain. Authentic British fish and chips. 116 North St, Bennington.

Cilantro. Farm to table tacos and burritos. 201 South St, Bennington.

Holy Cow Frozen Yogurt. Create your own dessert with a rotating selection of flavors and toppings. 411 Main St, Bennington.

Ramunto’s. New York-style brick oven pizza, subs, and entrees. Sports bar with more than 21 beers on tap. 519 Main St, Bennington.

Where to Sleep

Bennington hosts a wide range of overnight options in close proximity to the College. Reasonable for any price point, quaint New England inns and B&Bs stand nearby larger motel and hotel chains. For a broader range of options, visitors are encouraged to check Airbnb for additional accommodations.


Approx. 10 Min. Drive

Four Chimneys Inn. Rates starting at $139. 21 West Rd, Bennington.

Paradise Inn. Rates starting at $80. 141 Main St, Bennington.

South Shire Inn. Rates starting at $129. 124 Elm St, Bennington.

Approx. 20 Min. Drive

Arlington Inn. Rates starting at $159. 3904 VT-7A, Arlington.

Bed & Breakfasts

Approx. 5 Min. Drive

Eddington House Inn. Rates starting at $109. 21 Main St, North Bennington.

Taraden Bed and Breakfast. Rates starting at $75 (Airbnb). 183 Park St, North Bennington.

Approx. 30 Min. Drive

Ira Allen House. Rates starting at $120. 6311 VT-7A, Sunderland.

Hotels and Motels

Approx. 5 Min. Drive

Hampton Inn. Rates starting at $149. 51 Hannaford Square, Bennington.

Harwood Hill. Rates starting at $85. 864 Harwood Hill Rd, Bennington.

Knotty Pine Motel. Rates starting at $62. 130 Northside Dr, Bennington.

Best Western Bennington. Rates starting at $129. 220 Northside Dr, Bennington.

Approx. 10 Min. Drive

Bennington Motor Inn. Rates starting at $59. 143 Main St, Bennington.

Approx. 30 Min. Drive

Williamstown Motel. Rates starting at $54. 295 Main St, Williamstown, MA.

Where to Explore

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 Character

Approx. 10 Min. Drive

Bennington Bookshop. Bennington’s independently owned bookstore. Wi-Fi. 467 Main St, Bennington.

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

Bringing You Vermont. Restaurant and general store featuring local Vermont goods. 434 Main St, Bennington.

Hawkins House. Handmade gifts and jewelry. 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.

Camelot Village. Antiques, candles, cheeses, syrups. 66 Colgate Heights, Bennington.

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.


The Great Outdoors

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, 46 trails on 300 acres. 3984 VT-11, Peru. 

Jiminy Peak Mountain Resort. The only mountain resort in North America to generate its energy using wind power. 37 Corey Rd, Hancock, MA.

Mount Snow. 135 trails, 633 acres, serviced by 26 lifts. 89 Grand Summit Way, West Dover.

Stratton Mountain Ski Resort. 600 acres of top-ranked terrain, 94 trails, and 11 lifts. 5 Village Lodge Rd, Stratton.


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. 526 Union St, Manchester.


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.


For History Buffs

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. Robert Frost is buried in the cemetery at this historic church. 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. 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.

Art, Culture, and Entertainment

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

Village Picture Shows. Two-screen movie theater offering rotating selection of new releases. $6 locals' night on Mondays. 263 Depot St, Manchester Center.

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.

Downtown Bennington Vermont
Shops in downtown Bennington include the South Street Cafe, the independent Bennington Bookshop, and the Blue Benn, a vintage diner.
Bennington Monument
The monument at the center of Old Bennington is a memorial to the historic events that took place here in the Revolutionary War.
Pangaea Fine Dining
In the charming hamlet of North Bennington, you can find Pangaea, fine dining "for those used to the flawless choices in Manhattan" (The New York Times).