Jae's 7 Winter7 Winter StPittsfield, MA 01201(413) 464-8468 New American | BarsPrice range: ( 20 Yelp! reviews )Alta Restaurant & Wine Bar34 Church StLenox, MA 01240(413) 637-0003 New American | Wine Bars | Breakfast & BrunchPrice range: $$$( 386 Yelp! reviews )District Kitchen & Bar40 West StPittsfield, MA 01201(413) 442-0303 New American | GastropubsPrice range: $$( 293 Yelp! reviews )Lift Bistropub101 Dan Fox DrbousquetmountainPittsfield, MA 01201(413) 232-9362 New American | PubsPrice range: ( 16 Yelp! reviews )51 Park Restaurant & Tavern51 Park StLee, MA 01238(413) 243-2153 Pizza | Bars | AmericanPrice range: $$( 542 Yelp! reviews )Brava65 Church StLenox, MA 01240(413) 637-9171 Bars | Italian | Tapas/Small PlatesPrice range: $$( 297 Yelp! reviews )Sibaritas1264 East StPittsfield, MA 01201(413) 448-8244 ItalianPrice range: ( 105 Yelp! reviews )The Roasted Garlic483 W Housatonic StPittsfield, MA 01201(413) 499-9910 American | Sports BarsPrice range: $$( 201 Yelp! reviews )Once Upon a Table36 Main StStockbridge, MA 01262(413) 298-3870 AmericanPrice range: $$( 254 Yelp! reviews )Morgan House33 Main StLee, MA 01238(413) 243-3661 New American | AmericanPrice range: $$( 155 Yelp! reviews )Mario's Restaurant22 State Rte 20New Lebanon, NY 12125(518) 794-9495 Italian | New American | AmericanPrice range: $$$( 95 Yelp! reviews )Cafe Triskele150 Main StLee, MA 01238(413) 243-6397 FrenchPrice range: $$$( 259 Yelp! reviews )Bistro Zinc56 Church StLenox, MA 01240(413) 637-8800 French | LoungesPrice range: $$$( 225 Yelp! reviews )Olde Forge Restaurant125 N Main StLanesborough, MA 01237(413) 442-6797 American | Chicken WingsPrice range: $$( 351 Yelp! reviews )Olde Heritage Tavern12 Housatonic StLenox, MA 01240(413) 637-0884 Sports Bars | American | SandwichesPrice range: $$( 209 Yelp! reviews )Frankie's Ristorante Italiano80 Main StLenox, MA 01240(413) 637-4455 Italian | Wine BarsPrice range: $$( 180 Yelp! reviews )Pleasant and Main1063 Main StHousatonic, MA 01236(413) 274-6303 Cafes | Breakfast & Brunch | CreperiesPrice range: $$( 204 Yelp! reviews )Six Depot Roastery and Cafe6 Depot StWest Stockbridge, MA 01266(413) 232-0205 Cafes | Coffee RoasteriesPrice range: $$( 254 Yelp! reviews )La Fogata770 Tyler StPittsfield, MA 01201(413) 443-6969 ColombianPrice range: $$( 120 Yelp! reviews )Michael's5 Elm StStockbridge, MA 01262(413) 298-3530 American | New AmericanPrice range: $$( 94 Yelp! reviews )110 Grill - Lenox489 Pittsfield RdLenox, MA 01240(413) 296-1102 Gluten-Free | New American | Cocktail BarsPrice range: ( 17 Yelp! reviews )Avocado Cafe Lee5 Railroad StLee, MA 01238(413) 394-4022 MexicanPrice range: ( 50 Yelp! reviews )The Red Lion Inn30 Main StStockbridge, MA 01262(413) 298-5545 Hotels | New AmericanPrice range: $$$( 393 Yelp! reviews )Firefly Gastropub71 Church StLenox, MA 01240(413) 637-2700 New American | Comfort Food | GastropubsPrice range: $$$( 181 Yelp! reviews )Flo's Diner1245 W Housatonic StPittsfield, MA 01201(413) 442-3567 American | Breakfast & Brunch | VegetarianPrice range: $( 40 Yelp! reviews )Mazzeo's Ristorante1015 South StPittsfield, MA 01201(413) 448-2095 Italian | Gluten-Free | BarsPrice range: $$( 240 Yelp! reviews )Shire Breu-Hous63 Flansburg AveDalton, MA 01226(413) 842-8313 BrewpubsPrice range: $$( 52 Yelp! reviews )Alpamayo Restaurant60 Main StLee, MA 01238(413) 243-6000 Peruvian | Seafood | SoupPrice range: $$( 183 Yelp! reviews )Joe's Diner85 Center StLee, MA 01238(413) 243-9756 American | Breakfast & BrunchPrice range: $( 118 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 )Greylock Grounds Coffee20 Williamstown RdLanesborough, MA 01237 Pizza | Cafes | Coffee & TeaPrice range: ( 12 Yelp! reviews )Brooklyn's Best123 N StUnit APittsfield, MA 01201(413) 242-9050 Pizza | ItalianPrice range: $$( 39 Yelp! reviews )Wyndhurst Restaurant At Cranwell55 Lee RdLenox, MA 01240(413) 637-1364 Coffee & Tea | Breakfast & Brunch | BuffetsPrice range: $$$( 12 Yelp! reviews )Proprietor's Lodge22 Waubeek RdPittsfield, MA 01201(413) 344-9546 Hotels | Venues & Event Spaces | AmericanPrice range: ( 51 Yelp! reviews )Vongs157 Seymour StPittsfield, MA 01201(413) 442-6000 ThaiPrice range: $$( 109 Yelp! reviews )Patrick's Pub26 Bank RowPittsfield, MA 01201(413) 499-1994 Irish PubPrice range: $$( 151 Yelp! reviews )Main Street Café40 Main StStockbridge, MA 01262(413) 298-3060 Coffee & Tea | Ice Cream & Frozen YogurtPrice range: $$( 102 Yelp! reviews )Romans Restaurant and Ccuchifritos496 Tyler StPittsfield, MA 01201(413) 344-9166 Puerto Rican | SaladPrice range: ( 10 Yelp! reviews )Electra's Cafe439 Pittsfield RdLenox, MA 01240(413) 442-1000 Greek | AmericanPrice range: $$( 96 Yelp! reviews )Dewey's Public House16 Depot StDalton, MA 01226(413) 684-0900 Bars | AmericanPrice range: $$( 20 Yelp! reviews )Biggins Diggins543 S Main StLanesborough, MA 01237(413) 496-3141 Breakfast & BrunchPrice range: ( 46 Yelp! reviews )RJ'S Restaurant109 1st StPittsfield, MA 01201(413) 464-8204 Seafood | Italian | SaladPrice range: ( 63 Yelp! reviews )Roses Restaurant160 Housatonic StLee, MA 01238(413) 243-3333 Breakfast & BrunchPrice range: $$( 169 Yelp! reviews )Trattoria Rustica27 McKay StPittsfield, MA 01201(413) 499-1192 ItalianPrice range: $$$( 115 Yelp! reviews )Hudpucker's Pub & Grill101 Wahconah StPittsfield, MA 01201(413) 347-8025 Sports Bars | American | SandwichesPrice range: ( 8 Yelp! reviews )Salmon Run Fish House78 Main StLee, MA 01238(413) 243-3900 SeafoodPrice range: $$( 219 Yelp! reviews )Bob's Country Kitchen42 S Main StLanesborough, MA 01237(413) 499-3934 Breakfast & Brunch | DinersPrice range: $$( 132 Yelp! reviews )Haven Cafe & Bakery8 Franklin StLenox, MA 01240(413) 637-8948 Bakeries | CafesPrice range: $$( 342 Yelp! reviews )Zucchini's Restaurant1331 North StPittsfield, MA 01201(413) 442-2777 Italian | Venues & Event Spaces | AmericanPrice range: $$( 103 Yelp! reviews )Gateways Inn & Restaurant51 Walker StLenox, MA 01240(413) 637-2532 Bed & BreakfastPrice range: ( 43 Yelp! reviews )