Cheesecake Charlie's & Wholesome Harold's 60 Main Street, Lenox, MA 01240, 413-637-3411, This restaurant and bakery combo offers delicious American cuisine, desserts and a juice bar, as well as catering services. 

Olde Heritage Tavern, The 12 Housatonic Street, Lenox, MA 01240, 413-637-0884, This casual restaurant is housed in a building that was built in 1881, and serves from 11:30 AM until 10:00 PM daily; with a full bar, a relaxing atmosphere, and take out services, this tavern is known for having the “best hamburgers in town.”  

Roseborough Grill 71 Church Street, Lenox, MA 01240, 413-637-2700, The Roseborough Grill serves creative American cuisine, with a global influence, for lunch and dinner daily; also featured is a full bar with fine wines and other beverages, outdoor dining, Sunday night dancing, and catering services. 

Flavours 130 Pittsfield Road, Lenox, MA 01240, 413-637-3188, This restaurant serves American and Asian specialties. Open mic on Thursday night, Karaoke on Friday and live band on Saturday night.  more...

Bistro Zinc 56 Church Street, Lenox, MA 01240, 413-637-8800, This classic French bistro features eight different tap and specialty liquors, while serving traditional bistro fare in a warm, comfortable atmosphere. 

Church Street Cafe 65 Church Street, Lenox, MA 01240, 413-637-2745, The Church Street Café is an American bistro that serves an assortment of dishes that draw upon regional offerings and ethnic influences, while also offering a good selection of vegetarian dishes; lunch and dinner are served daily, and a full bar and patio dining are also featured. Luncheon and dinner menus are seasonal, but often feature such specialties as Asian spiced duck breast, roasted rack of lamb, grilled dry aged sirloin steaks, and many other notable entrées, as well as a wide selection of interesting appetizers.  more... 

Bev's Homemade Ice Cream & Cafe 36 Housatonic Street, Lenox, MA 01240, 413-637-0371, Known for its wonderful homemade ice cream, Bev’s also offers penny candy, specialty coffees, baked goods, lunches and boxed lunches, as well as tours of the ice cream factory.  

Lenox Coffee 52 Main Street, Lenox, MA 01240, 413-637-1606, This local coffee house is a nice gathering place, and serves, along with some of the finest roasted coffees, espressos, and coffee specialty beverages, a nice selection of teas and freshly baked goods.  more... 

Blantyre 16 Blantyre Road, Lenox, MA 01240, 413-637-3556, This award-winning fine restaurant specializes in refined cuisine, prepared using the freshest seasonal ingredients.  more...

Antonio's Ristorante 15 Franklin Street, Lenox, MA 01240, 413-637-9894, Antonio's Ristorante features authentic and classic Italian cuisine.  

Cafe Lucia 80 Church Street, PO Box 1796, Lenox, MA 01240, 413-637-2640, Cafe Lucia offers fine dining on regional Italian preparations and excellent wines. Alfresco dining on a mahogany covered deck is available in season. They are open for dinner only. more...

Lenox 218 Restaurant 218 Main Street, Route 7A, Lenox, MA 01240, Two Miles from Tanglewood, 413-637-4218, This contemporary and casual restaurant proffers wonderful Northern Italian and American cuisines, personable and attentive service, great desserts, an extensive list of fine wines, and much more. Private parties are welcome and can be easily accommodated, although reservations are recommended.  more...

Trattoria Il Vesuvio 242 Pittsfield Road, Lenox, MA 01240, Routes 7 and 20, 413-637-4904, Serving the finest in savoury, authentic Italian cuisine, this restaurant brings the taste of old Italy to the Berkshires, and offers weekly specials and an inviting atmosphere.  more... 

Spigalina Restaurant 80 Main Street, Lenox, MA 01240, 413-637-4455, This elegant restaurant offers innovative Mediterranean cuisine and a full bar, with outdoor dining available; open daily for dinner, at this restaurant reservations are recommended.