Smokey Divas239 Onota StPittsfield, MA 01201(413) 344-4206 BarbequePrice range: ( 59 Yelp! reviews )Once Upon a Table36 Main StStockbridge, MA 01262(413) 298-3870 AmericanPrice range: $$( 254 Yelp! reviews )The Marketplace Café53 North StPittsfield, MA 01201(413) 358-4777 Sandwiches | Coffee & Tea | CafesPrice range: $$( 210 Yelp! reviews )101 Restaurant & Bar1 West StPittsfield, MA 01201(413) 553-2251 Cocktail Bars | Sandwiches | SouthernPrice range: ( 16 Yelp! reviews )Wyndhurst Restaurant At Cranwell55 Lee RdLenox, MA 01240(413) 637-1364 Coffee & Tea | Breakfast & Brunch | BuffetsPrice range: $$$( 12 Yelp! reviews )Mad Jack's126 S Main StLanesborough, MA 01237(413) 442-2290 Barbeque | American | Soul FoodPrice range: ( 14 Yelp! reviews )Alta Restaurant & Wine Bar34 Church StLenox, MA 01240(413) 637-0003 New American | Wine Bars | Breakfast & BrunchPrice range: $$$( 386 Yelp! reviews )Brava65 Church StLenox, MA 01240(413) 637-9171 Bars | Italian | Tapas/Small PlatesPrice range: $$( 297 Yelp! reviews )Baja Charlie's62 W Center StLee, MA 01238(413) 243-4322 New American | MexicanPrice range: $$( 163 Yelp! reviews )Hudpucker's Pub & Grill101 Wahconah StPittsfield, MA 01201(413) 347-8025 Sports Bars | American | SandwichesPrice range: ( 8 Yelp! reviews )Bistro Zinc56 Church StLenox, MA 01240(413) 637-8800 French | LoungesPrice range: $$$( 225 Yelp! reviews )Old Man Jeff’s Barbecue Company370 Pecks RdPittsfield, MA 01201(413) 344-4244 BarbequePrice range: $$( 41 Yelp! reviews )Biggins Diggins543 S Main StLanesborough, MA 01237(413) 496-3141 Breakfast & BrunchPrice range: ( 46 Yelp! reviews )Frankie's Ristorante Italiano80 Main StLenox, MA 01240(413) 637-4455 Italian | Wine BarsPrice range: $$( 180 Yelp! reviews )51 Park Restaurant & Tavern51 Park StLee, MA 01238(413) 243-2153 Pizza | Bars | AmericanPrice range: $$( 542 Yelp! reviews )Pleasant and Main1063 Main StHousatonic, MA 01236(413) 274-6303 Cafes | Breakfast & Brunch | CreperiesPrice range: $$( 204 Yelp! reviews )Olde Forge Restaurant125 N Main StLanesborough, MA 01237(413) 442-6797 American | Chicken WingsPrice range: $$( 351 Yelp! reviews )Mazzeo's Ristorante1015 South StPittsfield, MA 01201(413) 448-2095 Italian | Gluten-Free | BarsPrice range: $$( 240 Yelp! reviews )Subway12845 Route 22Canaan, NY 12029(518) 781-4044 Sandwiches | Fast FoodPrice range: ( 5 Yelp! reviews )Jae's at the Hilton Garden Inn1032 South StThe Hilton Garden InnPittsfield, MA 01201(413) 464-8791 Sushi Bars | Pan Asian | Breakfast & BrunchPrice range: ( 106 Yelp! reviews )The Red Lion Inn30 Main StStockbridge, MA 01262(413) 298-5545 Hotels | New AmericanPrice range: $$$( 393 Yelp! reviews )The Bookstore11 Housatonic StLenox, MA 01240(413) 637-3390 Bookstores | Wine BarsPrice range: $$( 27 Yelp! reviews )Proprietor's Lodge22 Waubeek RdPittsfield, MA 01201(413) 344-9546 Hotels | Venues & Event Spaces | AmericanPrice range: ( 51 Yelp! reviews )Panchos Mexican Restaurant154 North StPittsfield, MA 01201(413) 499-2266 Mexican | Salad | SeafoodPrice range: $$( 111 Yelp! reviews )