Old Man Jeff’s Barbecue Company370 Pecks RdPittsfield, MA 01201(413) 344-4244 BarbequePrice range: $$( 41 Yelp! reviews )Smokey Divas239 Onota StPittsfield, MA 01201(413) 344-4206 BarbequePrice range: ( 59 Yelp! reviews )Mad Jack's126 S Main StLanesborough, MA 01237(413) 442-2290 Barbeque | American | Soul FoodPrice range: ( 14 Yelp! reviews )The K Shack9 Tilden RdNew Lebanon, NY 12125(518) 267-9330 Salad | BurgersPrice range: ( 26 Yelp! reviews )Lakehouse Inn615 Laurel StLee, MA 01238(413) 394-4256 BarbequePrice range: ( 0 Yelp! reviews )Biggins Diggins543 S Main StLanesborough, MA 01237(413) 496-3141 Breakfast & BrunchPrice range: ( 46 Yelp! reviews )BB's Hot Spot455 N StPittsfield, MA 01201(413) 464-9030 Caribbean | Barbeque | Chicken WingsPrice range: ( 7 Yelp! reviews )Blueberry Hill Market Cafe515 State Route 20New Lebanon, NY 12125(518) 794-2011 Cafes | Breakfast & Brunch | DessertsPrice range: $$( 286 Yelp! reviews )Rem Roc's117 Fenn StPittsfield, MA 01201(413) 448-8200 Sandwiches | Soul Food | Chicken WingsPrice range: ( 1 Yelp! reviews )Hudpucker's Pub & Grill101 Wahconah StPittsfield, MA 01201(413) 347-8025 Sports Bars | American | SandwichesPrice range: ( 8 Yelp! reviews )Hot Dog Ranch114 W Housatonic StPittsfield, MA 01201(413) 499-0055 Hot DogsPrice range: $( 64 Yelp! reviews )Olde Forge Restaurant125 N Main StLanesborough, MA 01237(413) 442-6797 American | Chicken WingsPrice range: $$( 351 Yelp! reviews )Baja Charlie's62 W Center StLee, MA 01238(413) 243-4322 New American | MexicanPrice range: $$( 163 Yelp! reviews )District Kitchen & Bar40 West StPittsfield, MA 01201(413) 442-0303 New American | GastropubsPrice range: $$( 293 Yelp! reviews )The Roasted Garlic483 W Housatonic StPittsfield, MA 01201(413) 499-9910 American | Sports BarsPrice range: $$( 201 Yelp! reviews )Beef Jerky Outlet17 Premium Outlet BlvdSte J440Lee, MA 01238 Specialty FoodPrice range: ( 2 Yelp! reviews )Romans Restaurant and Ccuchifritos496 Tyler StPittsfield, MA 01201(413) 344-9166 Puerto Rican | SaladPrice range: ( 10 Yelp! reviews )51 Park Restaurant & Tavern51 Park StLee, MA 01238(413) 243-2153 Pizza | Bars | AmericanPrice range: $$( 542 Yelp! reviews )Hangar of Pittsfield1350 East StPittsfield, MA 01201(413) 496-9464 Sports BarsPrice range: $$( 44 Yelp! reviews )Dalton HD Pizza1088 South StDalton, MA 01226(413) 842-5310 PizzaPrice range: ( 8 Yelp! reviews )101 Restaurant & Bar1 West StPittsfield, MA 01201(413) 553-2251 Cocktail Bars | Sandwiches | SouthernPrice range: ( 16 Yelp! reviews )Morgan House33 Main StLee, MA 01238(413) 243-3661 New American | AmericanPrice range: $$( 155 Yelp! reviews )Olde Heritage Tavern12 Housatonic StLenox, MA 01240(413) 637-0884 Sports Bars | American | SandwichesPrice range: $$( 209 Yelp! reviews )Berkshire Mountain Bakery180 Elm StPittsfield, MA 01201(413) 464-9394 Pizza | Bakeries | VeganPrice range: $( 97 Yelp! reviews )Electra's Cafe439 Pittsfield RdLenox, MA 01240(413) 442-1000 Greek | AmericanPrice range: $$( 96 Yelp! reviews )Pizza Bar380C Premium Outlet BlvdLee, MA 01238(413) 394-5816 PizzaPrice range: ( 2 Yelp! reviews )Firefly Gastropub71 Church StLenox, MA 01240(413) 637-2700 New American | Comfort Food | GastropubsPrice range: $$$( 181 Yelp! reviews )Samel's Deli and Catering115 Elm StPittsfield, MA 01201(413) 442-5927 DelisPrice range: $( 18 Yelp! reviews )Flo's Diner1245 W Housatonic StPittsfield, MA 01201(413) 442-3567 American | Breakfast & Brunch | VegetarianPrice range: $( 40 Yelp! reviews )Vivaldi's Pizzeria33 Park PlzLee, MA 01238(413) 243-4041 PizzaPrice range: $$( 57 Yelp! reviews )The Red Lion Inn30 Main StStockbridge, MA 01262(413) 298-5545 Hotels | New AmericanPrice range: $$$( 393 Yelp! reviews )Truc Orient Express Restaurant3 Harris StWest Stockbridge, MA 01266(413) 232-4204 Vietnamese | Salad | VegetarianPrice range: $$( 37 Yelp! reviews )Thistle And Mirth44 West StPittsfield, MA 01201(413) 344-4335 BarsPrice range: $( 47 Yelp! reviews )Roses Restaurant160 Housatonic StLee, MA 01238(413) 243-3333 Breakfast & BrunchPrice range: $$( 169 Yelp! reviews )The Starving Artist Creperie and Cafe40 Main StSte 2Lee, MA 01238(413) 394-5046 Creperies | CafesPrice range: $$( 287 Yelp! reviews )Bagel And Brew18 Franklin StLenox, MA 01240(413) 637-0055 Breakfast & Brunch | BagelsPrice range: $( 70 Yelp! reviews )Methuselah Bar and Lounge391 N StPittsfield, MA 01201(413) 347-2888 Wine Bars | Tapas/Small Plates | Cocktail BarsPrice range: $$( 94 Yelp! reviews )Arizona Pizza395 Pittsfield RdLenox, MA 01240(413) 442-9746 PizzaPrice range: $$( 127 Yelp! reviews )Locker Room Sports Pub232 Main StLee, MA 01238(413) 243-2662 American | Sports Bars | PubsPrice range: $$( 76 Yelp! reviews )Subway12845 Route 22Canaan, NY 12029(518) 781-4044 Sandwiches | Fast FoodPrice range: ( 5 Yelp! reviews )Teddy's Pizza & Restaurant508 East StPittsfield, MA 01201(413) 443-9030 PizzaPrice range: $$( 18 Yelp! reviews )99 Restaurants609 Merrill RdPittsfield, MA 01201(413) 236-0980 American | Seafood | PubsPrice range: $$( 56 Yelp! reviews )Hot Harry's Fresh Burritos403 Main StDalton, MA 01226(413) 300-0028 MexicanPrice range: ( 11 Yelp! reviews )Betty's Pizza Shack26 Housatonic StLenox, MA 01240(413) 637-8171 PizzaPrice range: $( 87 Yelp! reviews )McDonald's445 W Housatonic StPittsfield, MA 01201(413) 442-4629 Burgers | Fast Food | Coffee & TeaPrice range: $( 19 Yelp! reviews )East Lee Package Store185 Water StLee, MA 01238(413) 243-9768 Beer, Wine & Spirits | DelisPrice range: $( 17 Yelp! reviews )Prado’s Cafe85 Main StLee, MA 01238(413) 243-6561 Breakfast & Brunch | CafesPrice range: ( 35 Yelp! reviews )Chili's555 Hubbard AvePittsfield, MA 01201 Tex-Mex | Bars | AmericanPrice range: ( 44 Yelp! reviews )Subway236 Main StLee, MA 01238(413) 243-4142 SandwichesPrice range: $( 5 Yelp! reviews )Papa Gino's370 Stockbridge RdLee, MA 01238(413) 243-1380 PizzaPrice range: ( 5 Yelp! reviews )