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10 Great Dining Spots in the Berkshires

Posted on August 12, 2019Written by Lindsey Schmid
Updated on September 06, 2023

The Berkshires 10 Great Dining: Wheatleigh


Come and dine with us at The Portico by Jeffrey Thompson. We are the Berkshires only Forbes 5 Star/AAA 5 Diamond restaurant set in a stunning glass enclosed portico overlooking the stunning Berkshires hills. Looking for something more casual? Try out S/T Bistro (Simple and Tasty) which is Wheatleigh’s take on a casual bistro concept and discover fresh and tasty fare.


Discover The Conservatory at Blantyre, the area’s newest fine dining restaurant. Here you will be taken on an indulgent culinary journey with flavors found throughout the region. Chef de Cuisine Scott Cummings’ distinctive cuisine showcases two seasonal five-course tasting dinner menus which include a degustation and vegetarian option and wine pairings are also available.

Green Room Bar at Kemble Inn

Guests, locals, and visitors are raving about the Green Room Bar at Kemble Inn. Join us for one or more of out unique, signature cocktails in an intimate and casual atmosphere. The Green Room is the perfect backdrop for your night out in Lenox, MA. So be sure to stop by on your next trip to the Berkshires.

Freight Yard Pub & Restaurant

Freight Yard Pub & Restaurant located just one block South of MASS MoCA in Heritage State Park has seasonally rotating craft beer listed and boasts best burgers in the Berkshires. Established in 1991 locals and visitors can stop in for winter dining near fireplace or in a cool summer sit on the patio. Our made from scratch cooking makes our chef top notch. 

Trail House Kitchen and Bar

Trail House Kitchen & Bar, located between MASS MoCA and the Clark Art Institute, is a chic rustic bistro catering to the most adventurous of palettes. We offer an array of vegan and gluten free selections, while helping to support local businesses with fresh farm to table options.  Whether you are dining in or being catered to, the diverse menu options will delight.

Haflinger Haus Restaurant, Tavern & Inn

Make your reservations now at the Haflinger Haus and enjoy award-winning Austrian and American cuisine. Whether you want an elegant night out or a more casual place to gather, we have you covered. Be sure to try out one of our creative cocktails or sample one of our German beers.. Come taste why we have been voted Best of the Berkshires for 7 years in a row.

Berkshire Food Co-Op

Berkshire Food Co-op was founded by local families nearly 40 years ago to make good food available to everyone in the community. Since that time, we have been at the center of the local food scene, nurturing relationships with farmers and sourcing fresh food for our customers. With products from over 200 local vendors, there’s no better place to get a taste of the Berkshires!

8. Gateways Inn

9. Old Inn on the Green

10. John Andrews


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