Stockbridge Massachusetts Restaurants & Those Nearby

After enjoying our delicious home-cooked breakfast, we know it’ll be disappointing to leave the Inn for your next meal – luckily, one of the best reasons to visit the Berkshires is Stockbridge Massachusetts Restaurants and those nearby. There are tons of great places to grab lunch or make reservations for an elegant dinner. Listen to live jazz while you savor locally-sourced food, or dine at a casual bistro where authentic French cuisine meets American-style desserts. The restaurants in Stockbridge and the surrounding towns offer incredible quality and variety.

We love good food!  Below are some of our favorite restaurants in the area.  Ask us for recommendations or have us arrange your reservation. Whether you’re looking for someplace to celebrate a special occasion or want to find places close to the best of the Berkshires, we can help.

NOTICE: Due to the current COVID-19 pandemic, local businesses are adjusting their operations. Please visit the official sites for the businesses mentioned for up-to-date information. We also invite you to explore the Know Before You Go and 2020 What’s Open Page on our local tourism website for up to date info. Please also read our post for a Safe & Socially Distanced Berkshires Getaway.

Stockbridge Massachusetts Restaurants – 1.7 miles

Once Upon a Table

Once Upon a Table is a charming bistro-style restaurant tucked back in The Mews (a pedestrian alley) just off Stockbridge’s Main Street. They have been serving for nearly two decades, and are well known for both the quality of their food and service, as well as their low-key ambiance. For More Information: (413) 298-3870

Elm Street Market

America’s Downtown Market. Elm Street Market is a great local gathering place with an old-fashioned breakfast & lunch counter, deli and butcher shop. Open seven days a week, this market is a wonderful place to grab a delicious sandwich, stock up on high-quality groceries or get your fill of local gossip. For More Information: (413) 298-3634

The Red Lion Inn

The Red Lion Inn has developed a reputation for outstanding food and genuine New England hospitality. Those traditions are continued today by Executive Chef Brian J. Alberg, whose kitchen features contemporary American cuisine that is rooted in the region’s history. Emphasizing natural flavors and the use of fresh, local ingredients, Chef Alberg regularly updates the Inn’s menu to reflect the bounty of each changing season. There are three dining options available; the elegant Main Dining Room, the Widow Bingham Tavern and the Lion’s Den Pub (which has frequent entertainment). Serving lunch and dinner daily. For More Information: (413) 298-5545

Great Barrington – 9  miles

Café Adam

Offering a varied dinner menu, Café Adam features local produce and both classical and modern cooking techniques. Dishes such as hand-rolled fettuccine, braised meats, bouillabaisse, bistro steaks, and New Zealand lamb are available, as well as an ever-changing fish special offered each night with selections such as Atlantic Tuna, Rhode Island Striped Bass, French Durade, Bay of Fundy Halibut and Norwegian Cod. Serving dinner only. Our guests love their gluten-free offerings! For More Information: (413) 528-7786

Prairie Whale

Brooklyn restaurant pioneer Mark Firth brings the same rustic delicious food served at his previous restaurants — Diner and Marlow & Sons — to the Berkshires in the form of Prairie Whale. By using only the freshest produce and buying whole animals, they are able to use many different cuts of meat and make daily menu changes. New American cuisine. Serving dinner and lunch on the weekends.  Eclectic and delicious. For More Information: (413) 528-5050

Number Ten

Previously the Castle Street Cafe, Number Ten is a classic steakhouse in Great Barrington offering small plates of local fare, classic cocktails, and live entertainment on the weekends. Come unwind, celebrate, and explore at Number Ten! For More Information: (413) 528-5244

Lee – 4 miles


Formerly known as Bombay, MINT offers great Indian cuisine and lakeside dining. Located inside the Black Swan Inn overlooking Lake Laurel, MINT serves lunch and dinner. For More Information: (413) 243-6731

Café Triskele

A casual bistro in the Berkshires. Café Triskele is where a French chef from Brittany and an American pastry chef, working with a team of like-minded, talented people in both staff and suppliers, are able to bring a passion for cooking and eating well to the table.  From the integrity of the ingredients to the producers of the wines, Café Triskele brings attention to detail in both preparation and service, providing consistency, quality, and pleasure.  Serving dinner only, it is commonly a go-to restaurant for special occasions. Bon appétit! For More Information: (413) 243-6397

Joe’s Diner

Everything you can expect from a diner can be found at Joe’s Diner: small, cozy, plenty of memorabilia to occupy the mind, and yummy homestyle meals.  This famous local destination was the inspiration for Norman Rockwell’s “The Runaway.”  It has a very friendly atmosphere. However, it is not very big inside so space is very limited.  Add this to your must see if you visited the Norman Rockwell Museum and want to grab a quick bite to eat.  Serving breakfast, lunch, and dinner. For More Information: (413) 243-9756 

Lenox – 4.5 miles


Alta Restaurant & Wine Bar joined the beautiful Lenox village in the summer of 2008. The humble creation of three passionate restaurateurs, Alta is a favorite of both locals and visitors alike. With a dinner menu offering a variety of local and organic ingredients, the inspired Mediterranean cuisine is always fresh. The extensive wine list features selections from around the world, not to mention 24 delicious wines by the glass. Open for dinner 7 days a week.  For More Information: (413) 637-0003

Gateways Inn

Located in the heart of Lenox, the restaurant at the Gateways Inn exudes both luxury and comfort amid linen-covered tables, flowers of the season, and classical or modern music softly playing in the background — also try their piano bar for late night entertainment and dining. Please note: The lounge and bar have seasonal hours, so be sure to contact for availability. For More Information: (413) 637-2532


A creative American pasta bar, Nudel takes its inspiration from the bounty provided by the local farms and producers of Berkshire County.  They use local, organic, ethical, and natural ingredients whenever and as much as possible.  Serving dinner only. Reservations are now accepted and advised! For More Information: (413) 551-7183


Come in for a wide selection of wine by the glass, beer on tap, tapas, pizzas, cheese, and charcuterie.  Seating is first-come-first-serve.  Serving dinner only. For More Information: (413) 637-9171

Table Six

Between the historical ambiance, excellent service, and unmatched food, it is easy to see why Table Six is considered one of the finest dining experiences in the Berkshires. Enjoy lunch, dinner, breakfast on the weekends, or Sunday brunch. For More Information: (413) 637-4113

Haven Café & Bakery

Serving breakfast and lunch, Haven Café and Bakery focuses on serving beautiful high-quality organic food. Yum! For More Information: (413) 637-8948

Bistro Zinc

Bistro Zinc is a modern French bistro that boasts fine cuisine and a refined but welcoming atmosphere.  Delicious for lunch and dinner! For More Information: (413) 637-8800

Pittsfield – 12 miles


Tucked away near the railroad tracks in Pittsfield, Elizabeth’s is a true experience and a labor of love for the owner. Explore Elizabeth’s menu, but know that mandatory salad and Berkshire Mountain Bakery sourdough bread are a meal unto themselves. Save room for the fantastic pasta, too! Fills up fast, so make reservations early. For More Information: (413) 448-8244

District Kitchen

Contemporary American cuisine with gastropub influences in downtown Pittsfield. The surrounding region boasts a rich food and agricultural culture of which the restaurant takes full advantage by offering an ever-changing seasonal menu showcasing locally sourced ingredients. District Kitchen takes food seriously, preparing all food in-house and to-order according to the culinary whims of executive chef Taylor Hitchcock and his talented support staff. The bar is open late. For More Information: (413) 442-0303

South Egremont – 15 miles

John Andrews

John Andrews Farmhouse Restaurant specializes in regional American cuisine with an emphasis on local fresh and seasonal ingredients and Italian regional influences.  The food is crafted by Chef-Owner Dan Smith and his team, and highlights farms and food artisans in the Berkshires, Hudson Valley, and Northwestern Connecticut.  Serving dinner only. Worth the drive from the Inn! For More Information: (413) 528-3469

The Old Mill

A Berkshire dining favorite for over thirty-five years, The Old Mill is located in the heart of South Egremont. Enjoy their extensive menus and wine list in the elegant wood-accented dining room. Serving dinner only, they accept reservations for parties of 5 or more. For More Information: (413) 528-1421

New Marlborough – 16 miles

Old Inn on the Green

Nestled in the old Berkshire village of New Marlborough, the Old Inn on the Green is surrounded by rolling fields and meadows.  The Old Inn, once a stagecoach relay, offers fine dining in intimate candlelit dining rooms and seasonal al fresco dining on the canopied garden terrace off the taproom.  Beautiful! Book well in advance, this restaurant fills up fast. For More Information: (413) 229-7924

Williamstown –  30 miles

Mezze Bistro & Bar

Mezze Bistro & Bar serves contemporary American cuisine highlighting the best of the season in support of independent farmers and artisan producers. The food is handcrafted by chefs who take great care to source local and seasonal ingredients including farm-fresh produce, meats, cheeses, and bread. Menu items are paired alongside small-batch microbrews, locally distilled spirits, and seasonal small-production wines. A must-do in Williamstown, perhaps paired with a trip to the Williamstown Theater Festival or the Clark Museum. Serving dinner only. For More Information: (413) 458-0123

Pet-Friendly Berkshires Restaurants*

*Note: Please always call the named pet-friendly restaurants ahead to ensure porches, patios, etc. are open and accepting dogs at the time you plan to visit.