Number Ten10 Castle StGreat Barrington, MA 01230(413) 528-5244 SteakhousesPrice range: ( 116 Yelp! reviews )District Kitchen & Bar40 West StPittsfield, MA 01201(413) 442-0303 New American | GastropubsPrice range: $$( 293 Yelp! reviews )Steam Noodle Cafe286 Main StGreat Barrington, MA 01230(413) 566-6353 Noodles | ThaiPrice range: ( 88 Yelp! reviews )Caminito Steakhouse7 Old South StNorthampton, MA 01060(413) 387-6387 Argentine | Steakhouses | SaladPrice range: $$$( 148 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 )RJ'S Chatham1 Church StChatham, NY 12037(518) 392-6663 Seafood | Steakhouses | Pasta ShopsPrice range: ( 2 Yelp! reviews )Jae's 7 Winter7 Winter StPittsfield, MA 01201(413) 464-8468 New American | BarsPrice range: ( 20 Yelp! reviews )Sibaritas1264 East StPittsfield, MA 01201(413) 448-8244 ItalianPrice range: ( 105 Yelp! reviews )J Gilbert's Wood-Fired Steaks & Seafood185 Glastonbury BlvdGlastonbury, CT 06033(860) 659-0409 Steakhouses | Bars | SeafoodPrice range: $$$( 849 Yelp! reviews )Wm Farmer & Sons20 S Front StHudson, NY 12534(518) 828-1635 New American | Cocktail BarsPrice range: $$$( 315 Yelp! reviews )Alina's Ristorante96 Russell StHadley, MA 01035(413) 584-8000 Italian | MediterraneanPrice range: $$( 174 Yelp! reviews )Amenia Steak House4905 Rte 44Amenia, NY 12501(845) 789-1520 Steakhouses | BarsPrice range: $$( 54 Yelp! reviews )Folly33 W Main StWilmington, VT 05363(802) 464-1333 New AmericanPrice range: $$$( 80 Yelp! reviews )Once Upon a Table36 Main StStockbridge, MA 01262(413) 298-3870 AmericanPrice range: $$( 254 Yelp! reviews )Old Mill53 Main StRt 23South Egremont, MA 01258(413) 528-1421 New AmericanPrice range: $$$( 94 Yelp! reviews )HighBrow Wood Fired Kitchen & Bar12 Crafts AveNorthampton, MA 01060(413) 586-1468 Pizza | New American | Beer, Wine & SpiritsPrice range: $$( 205 Yelp! reviews )Prairie Whale178 Main StGreat Barrington, MA 01230(413) 528-5050 New AmericanPrice range: $$( 347 Yelp! reviews )The Roasted Garlic483 W Housatonic StPittsfield, MA 01201(413) 499-9910 American | Sports BarsPrice range: $$( 199 Yelp! reviews )Lift Bistropub101 Dan Fox DrbousquetmountainPittsfield, MA 01201(413) 232-9362 New American | PubsPrice range: ( 16 Yelp! reviews )Windsor Steak and Seafood35 Poquonock AveWindsor, CT 06095(860) 285-8424 Desserts | Seafood | SteakhousesPrice range: $$( 114 Yelp! reviews )The Blue Rock1 Ashfield StShelburne Falls, MA 01370(413) 625-8133 New American | Cocktail Bars | Beer BarPrice range: $$( 68 Yelp! reviews )Mt. Anthony Country Club - Restaurant and Vermont Weddings180 Country Club DrMt Anthony Country ClubBennington, VT 05201(802) 442-2617 New American | Burgers | SteakhousesPrice range: $$( 45 Yelp! reviews )Johnny's Tavern30 Boltwood WalkAmherst, MA 01002(413) 230-3818 New American | Burgers | Beer, Wine & SpiritsPrice range: $$( 393 Yelp! reviews )Bounti-Fare Restaurant200 Howland AveAdams, MA 01220(413) 743-0193 New AmericanPrice range: $$( 22 Yelp! reviews )The Woodland192 Sharon RdLakeville, CT 06039(860) 435-0578 New American | Desserts | Sushi BarsPrice range: $$$( 90 Yelp! reviews )T J Buckley's132 Elliot StBrattleboro, VT 05301(802) 257-4922 New AmericanPrice range: $$$$( 127 Yelp! reviews )Alta Restaurant & Wine Bar34 Church StLenox, MA 01240(413) 637-0003 New American | Wine Bars | Breakfast & BrunchPrice range: $$$( 386 Yelp! reviews )Morgan's Restaurant74 Interlaken RdSalisbury, CT 06039(860) 435-9879 New AmericanPrice range: $$$( 18 Yelp! reviews )Whetstone Station36 Bridge StBrattleboro, VT 05301(802) 490-2354 BreweriesPrice range: $$( 1129 Yelp! reviews )Feast and Floret13 S 3rd StHudson, NY 12534(518) 822-1500 ItalianPrice range: $$$( 206 Yelp! reviews )Hope & Olive44 Hope StGreenfield, MA 01301(413) 774-3150 American | BarsPrice range: $$( 327 Yelp! reviews )The Roosevelt Room112 N Greenbush RdSte FTroy, NY 12180(518) 244-3721 Steakhouses | Cocktail Bars | New AmericanPrice range: ( 28 Yelp! reviews )Peter Havens Restaurant32 Elliot StBrattleboro, VT 05301(802) 257-3333 Seafood | Wine Bars | Cocktail BarsPrice range: $$$( 115 Yelp! reviews )Kingsley Tavern14 N Main StKent, CT 06757(860) 592-0261 American | PubsPrice range: $$( 164 Yelp! reviews )Millbrook Cafe3290 Franklin AveMillbrook, NY 12545(845) 677-6956 CafesPrice range: $$( 53 Yelp! reviews )Gedney Farm34 Hartsville-New Marlboro RdNew Marlborough, MA 01230(413) 229-3131 Venues & Event Spaces | Vegetarian | AmericanPrice range: $$$( 39 Yelp! reviews )The Rustic Table320 Keene RdWinchester, NH 03470(603) 392-0296 American | Seafood | ItalianPrice range: $$( 65 Yelp! reviews )The New England House254 Marlboro Rd Route 9 WBrattleboro, VT 05301(802) 254-6886 Seafood | Steakhouses | New AmericanPrice range: $$( 56 Yelp! reviews )The Bistro Box937 S Main StGreat Barrington, MA 01230(413) 717-5958 American | Hot Dogs | SandwichesPrice range: $$( 176 Yelp! reviews )Cafe Adam420 Stockbridge RdSte 3Great Barrington, MA 01230(413) 528-7786 Modern EuropeanPrice range: $$$( 97 Yelp! reviews )Anchor Seafood Restaurant8 S Main StWilmington, VT 05363(802) 464-2112 Seafood | New American | BarsPrice range: $$( 262 Yelp! reviews )677 Prime677 BroadwayAlbany, NY 12207(518) 427-7463 Steakhouses | Seafood | Venues & Event SpacesPrice range: $$$$( 295 Yelp! reviews )Chatham Brewing59 Main StChatham, NY 12037(518) 697-0059 Breweries | Gastropubs | Music VenuesPrice range: $$( 130 Yelp! reviews )PUBLIC eat+drink34 Holden StNorth Adams, MA 01247(413) 664-4444 New American | GastropubsPrice range: $$( 483 Yelp! reviews )Water Street Grill123 Water StWilliamstown, MA 01267(413) 458-2175 AmericanPrice range: $$( 162 Yelp! reviews )225 Warren Bar and Grill225 Warren StHudson, NY 12534(518) 697-8225 American | Sports Bars | SandwichesPrice range: ( 62 Yelp! reviews )Alpamayo Restaurant60 Main StLee, MA 01238(413) 243-6000 Peruvian | Seafood | SoupPrice range: $$( 183 Yelp! reviews )Alpenglow Bistro9 W Main StWilmington, VT 05363(802) 464-4569 German | Cocktail Bars | AustrianPrice range: $$$( 43 Yelp! reviews )Governor's Tavern14 S 7th StHudson, NY 12534(518) 697-5609 American | Beer BarPrice range: $$( 124 Yelp! reviews )