The Spring Street Market & Cafe66 Spring StWilliamstown, MA 01267(413) 458-6192 CafesPrice range: $$( 52 Yelp! reviews )Village Roost Cafe & Marketplace20 W Main StWilmington, VT 05363(802) 464-3344 Cafes | Coffee & Tea | SandwichesPrice range: $$( 132 Yelp! reviews )Crazy Horse Bar & Grill66 Thunder Mountain Rdcharlemont, MA 01339(413) 339-6617 Bars | Salad | American (Traditional)Price range: ( 8 Yelp! reviews )PUBLIC eat+drink34 Holden StNorth Adams, MA 01247(413) 664-4444 American (New) | GastropubsPrice range: $$( 477 Yelp! reviews )The Barn Kitchen & Bar103 Spring StWilliamstown, MA 01267(978) 784-7602 Desserts | Salad | Breakfast & BrunchPrice range: ( 40 Yelp! reviews )Readsboro7077 Main StReadsboro, VT 05350(802) 423-7077 Hotels | Pubs | PizzaPrice range: $$( 15 Yelp! reviews )Bringing You Vermont434 Main StBennington, VT 05201(802) 753-7639 Specialty Food | Gift Shops | CafesPrice range: $$( 29 Yelp! reviews )The Marketplace Café53 North StPittsfield, MA 01201(413) 358-4777 Sandwiches | Coffee & Tea | CafesPrice range: $$( 208 Yelp! reviews )The Elm Street Market251 Elm StBennington, VT 05201(802) 753-7366 Delis | Sandwiches | Coffee & TeaPrice range: $( 92 Yelp! reviews )Beer Naked Brewery7678 Vermont Rte 9Marlboro, VT 05344(802) 464-7702 Pizza | BrewpubsPrice range: $$( 115 Yelp! reviews )Bigg Daddy's Philly Steak House2601 Mass MoCA WayNorth Adams, MA 01247(413) 346-4431 Barbeque | Burgers | CheesesteaksPrice range: ( 8 Yelp! reviews )The Publyk House782 Harwood Hill RdBennington, VT 05201(802) 442-7500 American (New) | SteakhousesPrice range: $$( 176 Yelp! reviews )The Break Room At Greylock Works508 State RdNorth Adams, MA 01247(413) 346-4035 Breakfast & Brunch | Cocktail BarsPrice range: $$( 52 Yelp! reviews )Trail 87271 VT-100West Dover, VT 05356(802) 464-2422 American (New) | BarsPrice range: ( 39 Yelp! reviews )Seeds Market Cafe1843 W Housatonic StPittsfield, MA 01201(413) 443-0188 American (New) | Salad | SandwichesPrice range: ( 5 Yelp! reviews )Trail House Kitchen & Bar896 State RdNorth Adams, MA 01247(413) 412-1090 Bars | American (New) | SeafoodPrice range: $$$( 124 Yelp! reviews )Dot's Restaurant3 W Main StWilmington, VT 05363(802) 464-7284 Diners | American (Traditional)Price range: $$( 276 Yelp! reviews )The 421 Craft Bar & Kitchen421 Main StBennington, VT 05201(802) 440-5972 Cocktail Bars | Tapas BarsPrice range: $$( 28 Yelp! reviews )The Vermont Country Deli436 Western AveBrattleboro, VT 05301(802) 257-9254 Delis | Specialty Food | SandwichesPrice range: $$( 252 Yelp! reviews )La Casita14 S Main StWilmington, VT 05301(802) 464-8500 Bars | MexicanPrice range: $$( 88 Yelp! reviews )The Maple Leaf Tavern3 North Main StWilmington, VT 05363(802) 464-8999 American (Traditional)Price range: $$( 101 Yelp! reviews )Sibaritas1264 East StPittsfield, MA 01201(413) 448-8244 ItalianPrice range: ( 103 Yelp! reviews )Wild Oats Market320 Main StWilliamstown, MA 01267(413) 458-8060 Grocery | Health Markets | Organic StoresPrice range: $$( 36 Yelp! reviews )The Last Chair267 Rte 100West Dover, VT 05356(802) 464-1133 Pizza | Burgers | SaladPrice range: $$( 160 Yelp! reviews )Madison Brewing Company Pub & Restaurant428 Main StBennington, VT 05201(802) 442-7397 Pubs | American (Traditional) | SandwichesPrice range: $$( 403 Yelp! reviews )TC's Restaurant178 Route 100West Dover, VT 05356(802) 464-5900 American (New)Price range: $$( 74 Yelp! reviews )Leo’s Table55 N Main StUnit ADeerfield, MA 01373(413) 397-3095 Breakfast & Brunch | American (Traditional) | SandwichesPrice range: ( 16 Yelp! reviews )Gypsy Apple Bistro65 Bridge StShelburne Falls, MA 01370(413) 625-6345 French | BarsPrice range: $$$( 51 Yelp! reviews )Valley View Saloon131 Rt 100West Dover, VT 05356(802) 464-9422 Sports Bars | American (New)Price range: $$( 153 Yelp! reviews )Bright Ideas Brewing111 Mass Moca WayNorth Adams, MA 01247(413) 346-4460 BreweriesPrice range: $$( 75 Yelp! reviews )Fall's Diner21418 State Rte 22Hoosick Falls, NY 12090(518) 686-5757 Diners | Breakfast & Brunch | American (Traditional)Price range: $( 38 Yelp! reviews )Hope & Olive44 Hope StGreenfield, MA 01301(413) 774-3150 American (Traditional) | BarsPrice range: $$( 320 Yelp! reviews )The Food Truck at The Nutmeg153 W Main StThe Nutmeg InnWilmington, VT 05363(802) 380-6101 Food TrucksPrice range: $$( 4 Yelp! reviews )1900' Burger39 Mount Snow DrMount SnowWest Dover, VT 05356(802) 464-7029 Burgers | American (Traditional)Price range: $$( 33 Yelp! reviews )The Store at Five Corners4 New Ashford RdRte 7 & 43Williamstown, MA 01267(413) 458-6105 Bakeries | Cafes | SandwichesPrice range: $$( 45 Yelp! reviews )Your Belly's Deli100 Pleasant StBennington, VT 05201(802) 442-3653 Sandwiches | Salad | WrapsPrice range: $( 41 Yelp! reviews )Bonnie B's204 Main StGreenfield, MA 01301(413) 475-3758 Breakfast & Brunch | American (Traditional)Price range: ( 51 Yelp! reviews )Berkshire Pizzeria72 Main StCharlemont, MA 01339(413) 337-5501 Pizza | Wraps | SandwichesPrice range: $( 54 Yelp! reviews )Water Street Grill123 Water StWilliamstown, MA 01267(413) 458-2175 American (Traditional)Price range: $$( 155 Yelp! reviews )Cuzzins Bar & Grill39 Mt Snow RdWest Dover, VT 05356 Bars | American (Traditional)Price range: $$( 30 Yelp! reviews )El Greco Cafe233 Main StGreenfield, MA 01301(413) 774-2844 Greek | MediterraneanPrice range: $( 65 Yelp! reviews )Cup N Saucer RestaurantDover RdWilmington, VT 05363(802) 464-5813 Breakfast & Brunch | DelisPrice range: $$( 61 Yelp! reviews )Marigold Kitchen Pizza25 Main StNorth Bennington, VT 05257(802) 445-4545 Pizza | Vegan | SaladPrice range: $$( 47 Yelp! reviews )Wild Roots11 Bridge StSunderland, MA 01375(413) 350-5911 Juice Bars & Smoothies | Breakfast & Brunch | SandwichesPrice range: $$( 54 Yelp! reviews )Bennington Dining-HallOne College DrNorth Bennington, VT 05201 DinersPrice range: ( 3 Yelp! reviews )Flo's Diner1245 W Housatonic StPittsfield, MA 01201(413) 442-3567 American (Traditional) | Breakfast & Brunch | VegetarianPrice range: $( 38 Yelp! reviews )Patrick's Pub26 Bank RowPittsfield, MA 01201(413) 499-1994 Irish PubPrice range: $$( 143 Yelp! reviews )Bamboo Asian Cuisine265 Greenfield RdUnit DDeerfield, MA 01373(413) 397-3477 Salad | Korean | Asian FusionPrice range: ( 1 Yelp! reviews )The Blue Rock1 Ashfield StShelburne Falls, MA 01370(413) 625-8133 American (New) | Cocktail Bars | Beer BarPrice range: $$( 65 Yelp! reviews )Thrive Diner145 Wahconah StPittsfield, MA 01201(413) 344-9353 VeganPrice range: $$( 81 Yelp! reviews )