Jae's 7 Winter7 Winter StPittsfield, MA 01201(413) 464-8468 New American | BarsPrice range: ( 20 Yelp! reviews )51 Park Restaurant & Tavern51 Park StLee, MA 01238(413) 243-2153 Pizza | Bars | AmericanPrice range: $$( 542 Yelp! reviews )Morgan House33 Main StLee, MA 01238(413) 243-3661 New American | AmericanPrice range: $$( 155 Yelp! reviews )District Kitchen & Bar40 West StPittsfield, MA 01201(413) 442-0303 New American | GastropubsPrice range: $$( 293 Yelp! reviews )Sibaritas1264 East StPittsfield, MA 01201(413) 448-8244 ItalianPrice range: ( 105 Yelp! reviews )Lift Bistropub101 Dan Fox DrbousquetmountainPittsfield, MA 01201(413) 232-9362 New American | PubsPrice range: ( 16 Yelp! reviews )Alta Restaurant & Wine Bar34 Church StLenox, MA 01240(413) 637-0003 New American | Wine Bars | Breakfast & BrunchPrice range: $$$( 386 Yelp! reviews )Cafe Triskele150 Main StLee, MA 01238(413) 243-6397 FrenchPrice range: $$$( 259 Yelp! reviews )Cafe Adam420 Stockbridge RdSte 3Great Barrington, MA 01230(413) 528-7786 Modern EuropeanPrice range: $$$( 97 Yelp! reviews )Brava65 Church StLenox, MA 01240(413) 637-9171 Bars | Italian | Tapas/Small PlatesPrice range: $$( 297 Yelp! reviews )Once Upon a Table36 Main StStockbridge, MA 01262(413) 298-3870 AmericanPrice range: $$( 254 Yelp! reviews )The Dream Away Lodge1342 County RdBecket, MA 01223(413) 623-8725 Bars | New AmericanPrice range: $$( 106 Yelp! reviews )Michael's5 Elm StStockbridge, MA 01262(413) 298-3530 American | New AmericanPrice range: $$( 94 Yelp! reviews )110 Grill - Lenox489 Pittsfield RdLenox, MA 01240(413) 296-1102 Gluten-Free | New American | Cocktail BarsPrice range: ( 17 Yelp! reviews )Wyndhurst Restaurant At Cranwell55 Lee RdLenox, MA 01240(413) 637-1364 Coffee & Tea | Breakfast & Brunch | BuffetsPrice range: $$$( 12 Yelp! reviews )The Red Lion Inn30 Main StStockbridge, MA 01262(413) 298-5545 Hotels | New AmericanPrice range: $$$( 393 Yelp! reviews )Dewey's Public House16 Depot StDalton, MA 01226(413) 684-0900 Bars | AmericanPrice range: $$( 20 Yelp! reviews )Avocado Cafe Lee5 Railroad StLee, MA 01238(413) 394-4022 MexicanPrice range: ( 50 Yelp! reviews )Frankie's Ristorante Italiano80 Main StLenox, MA 01240(413) 637-4455 Italian | Wine BarsPrice range: $$( 180 Yelp! reviews )The Roasted Garlic483 W Housatonic StPittsfield, MA 01201(413) 499-9910 American | Sports BarsPrice range: $$( 201 Yelp! reviews )Firefly Gastropub71 Church StLenox, MA 01240(413) 637-2700 New American | Comfort Food | GastropubsPrice range: $$$( 181 Yelp! reviews )Ozzie's Steak & Eggs26 Maple StHinsdale, MA 01235(413) 655-8309 New American | Breakfast & Brunch | SeafoodPrice range: $$( 88 Yelp! reviews )La Fogata770 Tyler StPittsfield, MA 01201(413) 443-6969 ColombianPrice range: $$( 120 Yelp! reviews )Alpamayo Restaurant60 Main StLee, MA 01238(413) 243-6000 Peruvian | Seafood | SoupPrice range: $$( 183 Yelp! reviews )Barrington Brewery & Restaurant420 Stockbridge RdGreat Barrington, MA 01230(413) 528-8282 American | Bars | BrewpubsPrice range: $$( 389 Yelp! reviews )Aegean Breeze Restaurant327 Stockbridge RdGreat Barrington, MA 01230(413) 528-4001 Mediterranean | GreekPrice range: $$( 197 Yelp! reviews )Proprietor's Lodge22 Waubeek RdPittsfield, MA 01201(413) 344-9546 Hotels | Venues & Event Spaces | AmericanPrice range: ( 51 Yelp! reviews )Agaves Mexican Grill389 Stockbridge RdGreat Barrington, MA 01230(413) 645-3281 New Mexican Cuisine | MexicanPrice range: ( 75 Yelp! reviews )Shire Breu-Hous63 Flansburg AveDalton, MA 01226(413) 842-8313 BrewpubsPrice range: $$( 52 Yelp! reviews )Mazzeo's Ristorante1015 South StPittsfield, MA 01201(413) 448-2095 Italian | Gluten-Free | BarsPrice range: $$( 240 Yelp! reviews )Vongs157 Seymour StPittsfield, MA 01201(413) 442-6000 ThaiPrice range: $$( 109 Yelp! reviews )Bistro Zinc56 Church StLenox, MA 01240(413) 637-8800 French | LoungesPrice range: $$$( 225 Yelp! reviews )RJ'S Restaurant109 1st StPittsfield, MA 01201(413) 464-8204 Seafood | Italian | SaladPrice range: ( 63 Yelp! reviews )Joe's Diner85 Center StLee, MA 01238(413) 243-9756 American | Breakfast & BrunchPrice range: $( 118 Yelp! reviews )Brooklyn's Best123 N StUnit APittsfield, MA 01201(413) 242-9050 Pizza | ItalianPrice range: $$( 39 Yelp! reviews )Trattoria Rustica27 McKay StPittsfield, MA 01201(413) 499-1192 ItalianPrice range: $$$( 115 Yelp! reviews )Jae's at the Hilton Garden Inn1032 South StThe Hilton Garden InnPittsfield, MA 01201(413) 464-8791 Sushi Bars | Pan Asian | Breakfast & BrunchPrice range: ( 106 Yelp! reviews )Romans Restaurant and Ccuchifritos496 Tyler StPittsfield, MA 01201(413) 344-9166 Puerto Rican | SaladPrice range: ( 10 Yelp! reviews )Olde Heritage Tavern12 Housatonic StLenox, MA 01240(413) 637-0884 Sports Bars | American | SandwichesPrice range: $$( 209 Yelp! reviews )Roses Restaurant160 Housatonic StLee, MA 01238(413) 243-3333 Breakfast & BrunchPrice range: $$( 169 Yelp! reviews )Salmon Run Fish House78 Main StLee, MA 01238(413) 243-3900 SeafoodPrice range: $$( 219 Yelp! reviews )Flo's Diner1245 W Housatonic StPittsfield, MA 01201(413) 442-3567 American | Breakfast & Brunch | VegetarianPrice range: $( 40 Yelp! reviews )Patrick's Pub26 Bank RowPittsfield, MA 01201(413) 499-1994 Irish PubPrice range: $$( 151 Yelp! reviews )Hudpucker's Pub & Grill101 Wahconah StPittsfield, MA 01201(413) 347-8025 Sports Bars | American | SandwichesPrice range: ( 8 Yelp! reviews )Koto Hibachi Steak House795 Dalton AvePittsfield, MA 01201(413) 770-7128 Sushi Bars | Japanese | SteakhousesPrice range: $$( 80 Yelp! reviews )El Sabor Dominicano496 Tyler StPittsfield, MA 01201(413) 344-9166 Puerto RicanPrice range: ( 0 Yelp! reviews )Haven Cafe & Bakery8 Franklin StLenox, MA 01240(413) 637-8948 Bakeries | CafesPrice range: $$( 342 Yelp! reviews )Chili's555 Hubbard AvePittsfield, MA 01201 Tex-Mex | Bars | AmericanPrice range: ( 44 Yelp! reviews )Zucchini's Restaurant1331 North StPittsfield, MA 01201(413) 442-2777 Italian | Venues & Event Spaces | AmericanPrice range: $$( 103 Yelp! reviews )Tavern At The A303 Crane AvePittsfield, MA 01201(413) 347-8002 New American | Music VenuesPrice range: ( 7 Yelp! reviews )