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Dining at Tourists Hotel.

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The 31 Essential Berkshires Restaurants

Where to find wild-yeasted pizza, farm-to-cone ice cream, brisket mac and cheese, banh xeo in idyllic Western Massachusetts

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Dining at Tourists Hotel.
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Nestled between two small mountain ranges — the Hoosac to the east and the Taconic to the west — Berkshire County, Massachusetts, is a year-round destination for city dwellers in the Northeast. Some come to leaf peep in the picturesque woods and stroll through small towns like North Adams and Great Barrington. Others come for the arts and theater, assembled by an eclectic blend of creatives who traded the lights of Broadway for rural splendor. Visitors come for many reasons, but they all stick around for the food.

The region has a proud farming history — it was home to the first agricultural fair in the United States in 1807 and launched the first community-supported agriculture program in North America in 1985. But what started as a farming community has transformed into a premier destination for great dining in New England, as innovative chefs transform the region’s bounty into delicious plates at hidden diners, pop-up pizza spots, and farm-side ice cream stands.

From candlelit dinners in centuries-old farmhouses to barbecue at a modern art museum, here are 31 reasons to head for the hills in the Berkshires.

Health experts consider dining out to be a high-risk activity for the unvaccinated; it may pose a risk for the vaccinated, especially in areas with substantial COVID transmission.

Stephanie Gravalese is a freelance food writer based in upstate New York and the Berkshires of western Massachusetts. She writes about food, farms, foraging, and the craft beer industry. Keep up with Stephanie at slowlivingkitchen.com.

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Note: Restaurants on this map are listed geographically.

1. A-OK Berkshire Barbeque

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2601 Mass MoCA Way
North Adams, MA 01247
(413) 398-5079
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Located in the former guardhouse on the Massachusetts Museum of Contemporary Art campus in North Adams, A-OK Berkshire Barbeque serves up four-hour smoked chickens, which diners can get whole or by the half or quarter bird. There are also sandwiches made with co-owner Alex Oster’s bread, including one topped with fennel and cheddar sausage, as well as plenty of sides, including mac and cheese, baked beans, and potato salad. Outdoor seating is available, but diners can also take their food into the nearby Bright Ideas Brewing. Make sure to come early, as A-OK stops serving lunch and dinner when they sell out.

A metal half-tray lined with wax paper. Large hunks of roasted chicken and pieces of baguette are piled on top
Chicken platter.
Alexandra Barker

2. The Airport Rooms at Tourists

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779 State Rd
North Adams, MA 01247
(413) 346-4933
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The chic Tourists hotel in North Adams has raised the bar on accommodations in the area without losing its connection to Berkshire’s culture and heritage. The hotel and its cocktail lounge, the Airport Rooms, are part of a 200-year-old restored rooming house with brown leather couches and decor to match. But there’s nothing old-fashioned about the food and drink menu, which includes caviar, burrata, steak frites, classic cocktails, and a small list of natural wines.

A bartender pours a drink from a mixing glass into a cocktail glass, inside a cutout bar surrounded by patterned wallpaper
Classic cocktails in a vintage setting
Nicole Franzen

3. Jack's Hot Dog Stand

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12 Eagle St
North Adams, MA 01247
(413) 664-9006
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Jack’s Hot Dog Stand started in 1917 as a nickel-a-dog operation serving hungry mill workers on their way home. The counter-service joint has doled out burgers, hot dogs, and hand-cut fries in its tiny space in downtown North Adams ever since. Today, its prices have risen, but the plain hot dogs and hamburgers are still under $2 apiece.

4. The Break Room

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508 State Rd
North Adams, MA 01247
(413) 346-4035
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The Break Room, a restaurant and bakery, serves as a coworking space, culinary incubator, and events location at the Greylock Works campus, a mixed-use project in a 19th-century mill. Pastry chefs Cynthia Walton and Amanda Perreault fill the bakery case with pain au chocolat, cinnamon buns, and seasonal fruit danishes; items regularly sell out, so morning workers usually get the best selection. At the same time, chef Brian Alberg brings a thoughtful approach to the menu on the restaurant side with such dishes as roasted chicken soup with hen-of-the-woods mushrooms and pork shoulder with vinegar peppers (locally sourced or made in-house).

A bowl of various donuts, including powdered with sugar and filled with jam
Donuts.
The Break Room

5. Mezze Bistro + Bar

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777 Cold Spring Rd Route 7
Williamstown, MA 01267
(413) 458-0123
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Executive chef and Mezze co-owner Nicholas Moulton won big on Food Network’s Guy’s Grocery Games in 2019, inspiring Guy Fieri to dub him the “veggie king.” The title fits Moulton even better off-screen at Mezze, where he works up a contemporary farm-to-table menu. Seasonal options might include miso-marinated bistro steak with roasted onion and delicata squash jam; scallion pancakes with lacinato kale; or petite butternut squash with beluga lentils, hen-of-the-woods mushrooms, and fermented squash-seed curry.

A large roasted squash half topped with mushrooms and other vegetables
Honeynut squash with beluga lentils, hen of the woods, and fermented squash seed curry.
Maddy Markland

6. Smokey Divas

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239 Onota St
Pittsfield, MA 01201
(413) 344-4206
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The granddaughter of Dorothy Turner Everett, who opened Oakland, California’s historic Everett & Jones Barbeque in 1973, Lorraine Jones started selling barbecue at the local farmers market as a vehicle for promoting her family’s barbecue sauce, 92nd Sauce. The prepared dishes were so popular, Jones opened her own takeout spot down a quiet Pittsfield street a few years later. Grab a plate of ribs, barbecue chicken, or smoked brisket, plus her legendary sides like macaroni and cheese and collard greens with smoked turkey.

From above, a table with lots of dishes lined with a checkerboard tablecloth. dishes include barbecued chicken, muffins, coleslaw, collard greens, mac and cheese, cake, sandwiches, and other barbecued meats
A full spread.
Smokey Divas/Facebook

7. Dottie's Coffee Lounge

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444 North St
Pittsfield, MA 01201
(413) 443-1792
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You’ll often see friends catching up over coffee or lunch at Dottie’s Coffee Lounge. Located in a historic building on downtown Pittsfield’s bustling North Street, the charming space features white brick walls and industrial light fixtures, giving off a rustic, bohemian vibe. The breakfast sandwiches hit the spot, especially the ones served on extra-large English muffins, and lunch brings such dishes as a grilled cheese with ghee and barbecue pulled-pork burritos. Dottie’s cupcakes and baked goods are also a must if you’re into something sweet.

From above, a cupcake with swirled icing, on a wooden table
Swirly cupcake.
Dottie’s Coffee Lounge

8. BB's Hot Spot

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302 Columbus Ave
Pittsfield, MA 01201
(413) 464-9030
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In his roving food truck and at his brick-and-mortar location, Ronny Brizan brings the flavors of his native Grenada to Berkshire diners. You can also find him serving the popular jerk or curried chicken, barbecue pork ribs, braised oxtail, and curried goat at local wineries, breweries, and even barbershops. Wash down your meal with some ginger beer or sorrel made in-house.

Someone uses tongs to rotate a chicken leg, over a grill with other pieces of basted chicken
Jerk chicken.
BB’s Hot Spot

9. East Side Cafe

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378 Newell St
Pittsfield, MA 01201
(413) 447-9405
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A Pittsfield staple for decades, East Side Cafe churns out coal-fired pizzas in a flash, and the pies are often accompanied by live music. Just be sure to keep track of the pizza schedule; while the cafe serves lunch sandwiches and some classic Italian dishes every day of the week, the kitchen only fires up the pizza oven from Thursday through Sunday.

10. La Chalupa y la Enchilada

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(413) 822-3053
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Find this family-owned Mexican food truck around town in downtown Pittsfield during the week and at nearby breweries and wineries on the weekends. Fan favorites include the tacos, burritos, taquitos, and tostadas, and there are rotating specials like chorizo tlayudas and dulce de leche churros. Follow it on Instagram and Facebook to see where it’s popping up next.

11. Berkshire Mountain Bakery Pizza Cafe

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180 Elm St
Pittsfield, MA 01201
(413) 464-9394
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The flagship Berkshire Mountain Bakery in Housatonic was featured on Michael Pollan’s 2016 Netflix series Cooked, where owner Richard Bourdon showed off the bakery’s famed white boule stuffed with dark chocolate chunks. The bakery’s regular loaves can be found throughout the region, including at local farmers markets, but if you want something heartier, the Pittsfield outpost offers pizzas, salads, and sandwiches in addition to Bourdon’s renowned pastries.

Two hands hold a large pizza on a wooden platter
Pizza from Berkshire Mountain Bakery.
Berkshire Mountain Bakery/Facebook

12. Hilltown Hot Pies

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745 Fischer Rd
Kinderhook, NY 12106

Hilltown Hot Pies isn’t your typical pizza spot. The seasonal pizza trailer sits on Katchkie Farm in the middle of Berkshire County. There, pizzaiolo Rafi Bildner serves “wild” (yeasted) pizzas with farm-fresh ingredients like garlic chive blossoms and spinach, which are grown a few feet away or sourced nearby.

A chef stands in front of pizza ovens with a large pizza topped with a variety of greens and vegetables
Rafi Bildner with one of his pies.
Hilltown Hot Pies

13. Haven

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8 Franklin St
Lenox, MA 01240
(413) 637-8948
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Cafe, bakery, brunch standby — whatever you call it, Haven offers a wide selection of delicious eats. The farm-fresh menu features sandwiches (croque monsieur, tuna bacon melt), daytime hits (croissant French toast), and salads (Aegean salad with artichoke hearts), along with many baked delicacies. In addition to freshly brewed coffee, Haven also offers a large variety of teas.

A oozing grilled cheese cut in half and stacked on a plate with side salad
Brie apple grilled cheese.
Haven/Facebook

14. Bagel & Brew

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18 Franklin St
Lenox, MA 01240
(413) 637-0055
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Bagel & Brew has you covered from day to night. Starting in the morning, there are classic New York-style bagels with a range of toppings and spreads, as well as sandwiches like the lumberjack topped with bacon cream cheese. Come back in the evening and head to the beer garden, where you can accompany your choice of draft beer with a full menu of comfort food favorites like pretzels with house-made beer cheese sauce and loaded hot dogs.

A hot dog dressed with toppings in a paper-lined basket with potato chips, beside a beer and a branded napkin holder

Honolulu dog with pineapple salsa, sweet chile sauce, bacon, and sesame seeds.

Bagel & Brew/Facebook

15. Brava

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65 Church St
Lenox, MA 01240
(413) 637-9171
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Whether you’re coming from a performance at Shakespeare & Company in the summer or you need somewhere to cozy up on a winter evening, Brava is the late-night food spot to know in Lenox. Open until 11:30 every night, it’s the perfect place to share a few tapas or a pizza with friends as you explore the extensive beer and wine list.

Diners sit at tables along a wine-rack lined wall and at a bar, in a low-lit tavern like room
Inside Brava.
Brava/Facebook

16. Nudel

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37 Church St
Lenox, MA 01240
(413) 551-7183
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Every six months or so, Bjorn Somlo of Nudel and his team reinvent their menu and restaurant concept, keeping seasonal ingredients as a through line. The current iteration, Nudel Bar, offers new takes on American comfort dishes like pork galumpkis (stuffed cabbage) with marrow tomato sauce, duck cassoulet, and spicy sweet potato soup with green curry. Grab a seat at the counter to chat with the kitchen crew. It’s the spot to be on a Friday night.

17. Truc Orient Express

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3 Harris St
West Stockbridge, MA 01266
(413) 232-4204
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This Vietnamese restaurant in West Stockbridge specializes in vegetarian and vegan dishes, though there’s plenty to satiate carnivores, too. Its vegetarian pho is healthy, nutritionally balanced, and satisfying. And the banh xeo (listed as “happy pancakes” and filled with vegetables, meat, or shrimp) appear on nearly every table. Big tastes are packed into this small restaurant.

Hefty vegetable fillings spill out of a banh xeo
Banh xeo.
Truc Orient Express Restaurant

18. The Farmstead Creamery

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535 Summer St
Lee, MA 01238

Join the Jersey cows strolling the fields and taking in the views at this farm and ice cream shop in Lee. Located at High Lawn Farm, the Farmstead Creamery serves flavors like sweet cream, chocolate chip, and purple cow (black raspberry ice cream with white and black chocolate chips). You can stock up on Berkshire provisions at the same time, including cheeses, meats, preserves, pickles, and maple syrup. If you’d prefer savory to sweet snacks, order a cheese and charcuterie platter featuring the dairy’s cheese and local accouterments, and find some seats among the picnic tables outside.

Cones of ice cream splayed on a wooden surface
A variety of cones.
The Farmstead Creamery

19. Alpamayo Peruvian Cuisine

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60 Main St
Lee, MA 01238
(413) 243-6000
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Alpamayo has been a local favorite in downtown Lee since 2010, offering Peruvian classics such as lomo saltado and ceviche. Chef Javier Fernandez, who owns the place with his wife, Alicia, was an award-winning bartender, so definitely don’t pass on the cocktail menu, which includes a stunning pisco sour and refreshing chilcano (pisco, ginger beer, lime). 

A plate of various types of fried seafood
Fried seafood platter.
Alpamayo Peruvian Cuisine

20. The Lost Lamb

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31 Main St
Stockbridge, MA 01262
(413) 298-7156
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The Lost Lamb is just as cozy as any other restaurant on Main Street in downtown Stockbridge, but the patisserie adds an easygoing French twist, making you feel as if you’ve stumbled onto a quiet side street in Paris. Le Cordon Bleu grad Claire Raposo is the dynamo behind all the bread, pastries, and desserts, like her luxurious olive oil orange bundt cake. Try the prosciutto and gruyere sandwich on a house-made baguette if you’re craving something savory.

A variety of fruit-topped cakes, and one topped with full macarons, on a sill in a sunny window
Cakes.
The Lost Lamb

21. The Red Lion Inn

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30 Main St
Stockbridge, MA 01262
(413) 298-5545
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The Red Lion Inn fits right in on Main Street in Stockbridge, famously painted by Norman Rockwell, and the old-fashioned vibes go deeper than the exterior. From the lace tablecloths and pewter chargers to the traditional New England dishes, everything about a meal here harkens back to an old-world form of dining. Enjoy a glass of wine in the hotel lobby near the fireplace, or head for the historic front porch with a hot toddy for the best seats in the house.

A fancy restaurant interior, with dark red carpeting, chandeliers, and tables set with white tablecloths
The dining room.
The Red Lion Inn/Facebook

22. Pleasant & Main

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1063 Main St
Housatonic, MA 01236
(413) 274-6303
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Located in a 19th-century storefront in the charming village of Housatonic, Pleasant & Main serves meals throughout the day in an airy yet intimate dining room with soft lighting, mix-and-match tables and chairs, and antiques everywhere. Pastries, egg dishes, and pancakes make up the best of breakfast; lunch brings crepes both sweet and savory; and dinner features hearty seasonal specials. Outdoor dining is available near a fire pit.

A mishmash of tables and chairs on a gravel outdoor seating area beneath large patio umbrellas
Patio seating.
Pleasant & Main/Facebook

23. The Prairie Whale

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178 Main St
Great Barrington, MA 01230
(413) 528-5050
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At the Prairie Whale, owner Mark Firth (formerly of Brooklyn’s Diner, Bonita, and Marlo & Sons) and chef Stephen Browning apply modern twists to classic dishes like pig head rillettes and brick chicken. A handful of specials highlight the best of whatever arrives from a growing network of local farms. Grab a seat at the bar, a cozy table, or a spot on a communal bench.

A sign for the Prairie Whale restaurant, with outdoor seating beneath string lights visible beyond
Outside the Prairie Whale.
The Prairie Whale

24. Marjoram + Roux

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47 Railroad St
Great Barrington, MA 01230
(413) 528-1223
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Located in the heart of downtown Great Barrington, Marjoram + Roux cafe offers breakfast and lunch options made with local ingredients. Recent specials have included rabbit and prune pate, pork rillettes on local toast with pickles and cranberry pear mustard, and duck confit salad with radicchio, radishes, almonds, and gorgonzola. Grab food to go, or enjoy a coffee or lunch outside in the warmer months. Don’t forget to pick up baked goods, especially the chocolate habanero bread or a walnut roll, on your way out.

A restaurant exterior, with a brand sign on a window, with bright blue metal patio seats and chairs on the sidewalk
Outside Marjoram + Roux.
Marjoram + Roux

25. Mooncloud

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47 Railroad St
Great Barrington, MA 01230

At the far end of Railroad Street in downtown Great Barrington, Mooncloud offers inventive craft cocktails as well as creative cheese boards and tinned fish to soak up the drinks. The sister bar to Cantina 229 in New Marlborough, Mooncloud isn’t afraid to be playful with serious ingredients: Consider the Professor X, essentially a Dr Pepper highball with Amaro Dell’ Etna, Lustau Brandy de Jerez, and cherry vanilla Cola. There’s also an impressive selection of nonalcoholic beverage options for those who want an evening out without imbibing.

A bartender spritzes the top of a cocktail filled with crushed ice
Spritzing a cocktail.
Mooncloud

26. Taqueria Azteca

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284 Main St
Great Barrington, MA 01230
(413) 528-3322
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Handmade tortillas, flame-grilled meats, hearty salsas (including a spicy green tomatillo option), and reasonable prices attract customers to this cozy Mexican spot in downtown Great Barrington. Order from a list of classic burrito combinations or design your own with tinga, chorizo, mushrooms in chipotle sauce, and plenty of toppings.

27. Steam

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286 Main St
Great Barrington, MA 01230
(413) 566-6353
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Tucked into the ground floor of the Barrington House atrium, the noodle cafe Steam offers convenient lunch or dinner on the go (you can also take your meal right outside to the Barrington Courtyard seating area, shared with neighboring food businesses). Chef and owner Phornphimon (Jem) Ezinga cooks up a pan-Asian menu of steamed buns, curry puffs, summer rolls, and banh xeo wraps, but the ramen is the star of the menu.

A decorative bowl of khao soi, with pickled vegetables on the side
Khao soi gai.
Steam

28. Number Ten

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10 Castle St
Great Barrington, MA 01230
(413) 528-5244
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Located right around the corner from the historic Mahaiwe Performing Arts Center in Great Barrington, Number Ten is a steakhouse that serves grass-fed, hormone-free proteins in keeping with the traditions of the Berkshires. There’s also an impressive selection of spirits, including what the restaurant claims is the largest selection of American whiskeys in the region. Head bartender David Guenette is happy to provide deep dives into the history of your favorite cocktail mainstays, too. When in doubt, get the burger.

An oval dish filled with mac and cheese, topped with a heavy portion of chopped brisket and herbs
Brisket mac and cheese.
Number Ten/Facebook

29. The Bistro Box

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937 S Main St
Great Barrington, MA 01230
(413) 717-5958
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A seasonal roadside burger and sandwich joint, the Bistro Box offers delicious and creative sandwiches made with fresh, seasonal ingredients. You can’t go wrong with the roadside burger or the farm frank, a local no-nitrate hot dog paired with french fries.

People wait in line to order at a roadside hut restaurant
The line outside the Bistro Box.
The Bistro Box

30. John Andrews Farmhouse

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224 Hillsdale Rd
Egremont, MA 01230
(413) 528-3469
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Tucked away in the woods of Egremont, this hidden gem is warm, romantic, and inviting. Executive chef/owner Dan Smith has developed a simple menu of dishes that reflect the origins of their ingredients, often sourced from local farmers and food makers. Classics are labeled on the menu with the year of their creation, like the fried oyster salad or the seared duck breast and crispy confit leg served with haricot vert, mashed potatoes, balsamic, and maple syrup.

A rustic farmhouse, in an idyllic fall woodsy scene
Outside John Andrews Farmhouse.
John Andrews Farmhouse

31. The Old Inn on the Green

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134 Hartsville-New Marlboro Road
New Marlborough, MA 01230
(413) 229-7924
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The irresistible Old Inn on the Green has pulled in plenty of travelers along Route 57 since the 18th century. Set amid lush greenery, the inn invites guests to indulge in a rustic dining experience by candlelight. Dine inside on fresh white linen tablecloths surrounded by giant oak beams, or relax outside on the canopied garden terrace. Currently, the restaurant only offers its prix fixe menu at $65 per person.

A dining room with a fire in the fireplace, idyllic wallpaper, dark wood paneling, tables with rustic chairs set for dinner with candles
The dining room.
The Old Inn on the Green

1. A-OK Berkshire Barbeque

2601 Mass MoCA Way, North Adams, MA 01247
A metal half-tray lined with wax paper. Large hunks of roasted chicken and pieces of baguette are piled on top
Chicken platter.
Alexandra Barker

Located in the former guardhouse on the Massachusetts Museum of Contemporary Art campus in North Adams, A-OK Berkshire Barbeque serves up four-hour smoked chickens, which diners can get whole or by the half or quarter bird. There are also sandwiches made with co-owner Alex Oster’s bread, including one topped with fennel and cheddar sausage, as well as plenty of sides, including mac and cheese, baked beans, and potato salad. Outdoor seating is available, but diners can also take their food into the nearby Bright Ideas Brewing. Make sure to come early, as A-OK stops serving lunch and dinner when they sell out.

2601 Mass MoCA Way
North Adams, MA 01247

2. The Airport Rooms at Tourists

779 State Rd, North Adams, MA 01247
A bartender pours a drink from a mixing glass into a cocktail glass, inside a cutout bar surrounded by patterned wallpaper
Classic cocktails in a vintage setting
Nicole Franzen

The chic Tourists hotel in North Adams has raised the bar on accommodations in the area without losing its connection to Berkshire’s culture and heritage. The hotel and its cocktail lounge, the Airport Rooms, are part of a 200-year-old restored rooming house with brown leather couches and decor to match. But there’s nothing old-fashioned about the food and drink menu, which includes caviar, burrata, steak frites, classic cocktails, and a small list of natural wines.

779 State Rd
North Adams, MA 01247

3. Jack's Hot Dog Stand

12 Eagle St, North Adams, MA 01247

Jack’s Hot Dog Stand started in 1917 as a nickel-a-dog operation serving hungry mill workers on their way home. The counter-service joint has doled out burgers, hot dogs, and hand-cut fries in its tiny space in downtown North Adams ever since. Today, its prices have risen, but the plain hot dogs and hamburgers are still under $2 apiece.

12 Eagle St
North Adams, MA 01247

4. The Break Room

508 State Rd, North Adams, MA 01247
A bowl of various donuts, including powdered with sugar and filled with jam
Donuts.
The Break Room

The Break Room, a restaurant and bakery, serves as a coworking space, culinary incubator, and events location at the Greylock Works campus, a mixed-use project in a 19th-century mill. Pastry chefs Cynthia Walton and Amanda Perreault fill the bakery case with pain au chocolat, cinnamon buns, and seasonal fruit danishes; items regularly sell out, so morning workers usually get the best selection. At the same time, chef Brian Alberg brings a thoughtful approach to the menu on the restaurant side with such dishes as roasted chicken soup with hen-of-the-woods mushrooms and pork shoulder with vinegar peppers (locally sourced or made in-house).

508 State Rd
North Adams, MA 01247

5. Mezze Bistro + Bar

777 Cold Spring Rd Route 7, Williamstown, MA 01267
A large roasted squash half topped with mushrooms and other vegetables
Honeynut squash with beluga lentils, hen of the woods, and fermented squash seed curry.
Maddy Markland

Executive chef and Mezze co-owner Nicholas Moulton won big on Food Network’s Guy’s Grocery Games in 2019, inspiring Guy Fieri to dub him the “veggie king.” The title fits Moulton even better off-screen at Mezze, where he works up a contemporary farm-to-table menu. Seasonal options might include miso-marinated bistro steak with roasted onion and delicata squash jam; scallion pancakes with lacinato kale; or petite butternut squash with beluga lentils, hen-of-the-woods mushrooms, and fermented squash-seed curry.

777 Cold Spring Rd Route 7
Williamstown, MA 01267

6. Smokey Divas

239 Onota St, Pittsfield, MA 01201
From above, a table with lots of dishes lined with a checkerboard tablecloth. dishes include barbecued chicken, muffins, coleslaw, collard greens, mac and cheese, cake, sandwiches, and other barbecued meats
A full spread.
Smokey Divas/Facebook

The granddaughter of Dorothy Turner Everett, who opened Oakland, California’s historic Everett & Jones Barbeque in 1973, Lorraine Jones started selling barbecue at the local farmers market as a vehicle for promoting her family’s barbecue sauce, 92nd Sauce. The prepared dishes were so popular, Jones opened her own takeout spot down a quiet Pittsfield street a few years later. Grab a plate of ribs, barbecue chicken, or smoked brisket, plus her legendary sides like macaroni and cheese and collard greens with smoked turkey.

239 Onota St
Pittsfield, MA 01201

7. Dottie's Coffee Lounge

444 North St, Pittsfield, MA 01201
From above, a cupcake with swirled icing, on a wooden table
Swirly cupcake.
Dottie’s Coffee Lounge

You’ll often see friends catching up over coffee or lunch at Dottie’s Coffee Lounge. Located in a historic building on downtown Pittsfield’s bustling North Street, the charming space features white brick walls and industrial light fixtures, giving off a rustic, bohemian vibe. The breakfast sandwiches hit the spot, especially the ones served on extra-large English muffins, and lunch brings such dishes as a grilled cheese with ghee and barbecue pulled-pork burritos. Dottie’s cupcakes and baked goods are also a must if you’re into something sweet.

444 North St
Pittsfield, MA 01201

8. BB's Hot Spot

302 Columbus Ave, Pittsfield, MA 01201
Someone uses tongs to rotate a chicken leg, over a grill with other pieces of basted chicken
Jerk chicken.
BB’s Hot Spot

In his roving food truck and at his brick-and-mortar location, Ronny Brizan brings the flavors of his native Grenada to Berkshire diners. You can also find him serving the popular jerk or curried chicken, barbecue pork ribs, braised oxtail, and curried goat at local wineries, breweries, and even barbershops. Wash down your meal with some ginger beer or sorrel made in-house.

302 Columbus Ave
Pittsfield, MA 01201

9. East Side Cafe

378 Newell St, Pittsfield, MA 01201

A Pittsfield staple for decades, East Side Cafe churns out coal-fired pizzas in a flash, and the pies are often accompanied by live music. Just be sure to keep track of the pizza schedule; while the cafe serves lunch sandwiches and some classic Italian dishes every day of the week, the kitchen only fires up the pizza oven from Thursday through Sunday.

378 Newell St
Pittsfield, MA 01201

10. La Chalupa y la Enchilada

Pittsfield, MA 01201

Find this family-owned Mexican food truck around town in downtown Pittsfield during the week and at nearby breweries and wineries on the weekends. Fan favorites include the tacos, burritos, taquitos, and tostadas, and there are rotating specials like chorizo tlayudas and dulce de leche churros. Follow it on Instagram and Facebook to see where it’s popping up next.

11. Berkshire Mountain Bakery Pizza Cafe

180 Elm St, Pittsfield, MA 01201
Two hands hold a large pizza on a wooden platter
Pizza from Berkshire Mountain Bakery.
Berkshire Mountain Bakery/Facebook

The flagship Berkshire Mountain Bakery in Housatonic was featured on Michael Pollan’s 2016 Netflix series Cooked, where owner Richard Bourdon showed off the bakery’s famed white boule stuffed with dark chocolate chunks. The bakery’s regular loaves can be found throughout the region, including at local farmers markets, but if you want something heartier, the Pittsfield outpost offers pizzas, salads, and sandwiches in addition to Bourdon’s renowned pastries.

180 Elm St
Pittsfield, MA 01201

12. Hilltown Hot Pies

745 Fischer Rd, Kinderhook, NY 12106
A chef stands in front of pizza ovens with a large pizza topped with a variety of greens and vegetables
Rafi Bildner with one of his pies.
Hilltown Hot Pies

Hilltown Hot Pies isn’t your typical pizza spot. The seasonal pizza trailer sits on Katchkie Farm in the middle of Berkshire County. There, pizzaiolo Rafi Bildner serves “wild” (yeasted) pizzas with farm-fresh ingredients like garlic chive blossoms and spinach, which are grown a few feet away or sourced nearby.

745 Fischer Rd
Kinderhook, NY 12106

13. Haven

8 Franklin St, Lenox, MA 01240
A oozing grilled cheese cut in half and stacked on a plate with side salad
Brie apple grilled cheese.
Haven/Facebook

Cafe, bakery, brunch standby — whatever you call it, Haven offers a wide selection of delicious eats. The farm-fresh menu features sandwiches (croque monsieur, tuna bacon melt), daytime hits (croissant French toast), and salads (Aegean salad with artichoke hearts), along with many baked delicacies. In addition to freshly brewed coffee, Haven also offers a large variety of teas.

8 Franklin St
Lenox, MA 01240

14. Bagel & Brew

18 Franklin St, Lenox, MA 01240
A hot dog dressed with toppings in a paper-lined basket with potato chips, beside a beer and a branded napkin holder

Honolulu dog with pineapple salsa, sweet chile sauce, bacon, and sesame seeds.

Bagel & Brew/Facebook

Bagel & Brew has you covered from day to night. Starting in the morning, there are classic New York-style bagels with a range of toppings and spreads, as well as sandwiches like the lumberjack topped with bacon cream cheese. Come back in the evening and head to the beer garden, where you can accompany your choice of draft beer with a full menu of comfort food favorites like pretzels with house-made beer cheese sauce and loaded hot dogs.

18 Franklin St
Lenox, MA 01240

15. Brava

65 Church St, Lenox, MA 01240
Diners sit at tables along a wine-rack lined wall and at a bar, in a low-lit tavern like room
Inside Brava.
Brava/Facebook

Whether you’re coming from a performance at Shakespeare & Company in the summer or you need somewhere to cozy up on a winter evening, Brava is the late-night food spot to know in Lenox. Open until 11:30 every night, it’s the perfect place to share a few tapas or a pizza with friends as you explore the extensive beer and wine list.

65 Church St
Lenox, MA 01240

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16. Nudel

37 Church St, Lenox, MA 01240

Every six months or so, Bjorn Somlo of Nudel and his team reinvent their menu and restaurant concept, keeping seasonal ingredients as a through line. The current iteration, Nudel Bar, offers new takes on American comfort dishes like pork galumpkis (stuffed cabbage) with marrow tomato sauce, duck cassoulet, and spicy sweet potato soup with green curry. Grab a seat at the counter to chat with the kitchen crew. It’s the spot to be on a Friday night.

37 Church St
Lenox, MA 01240

17. Truc Orient Express

3 Harris St, West Stockbridge, MA 01266
Hefty vegetable fillings spill out of a banh xeo
Banh xeo.
Truc Orient Express Restaurant

This Vietnamese restaurant in West Stockbridge specializes in vegetarian and vegan dishes, though there’s plenty to satiate carnivores, too. Its vegetarian pho is healthy, nutritionally balanced, and satisfying. And the banh xeo (listed as “happy pancakes” and filled with vegetables, meat, or shrimp) appear on nearly every table. Big tastes are packed into this small restaurant.

3 Harris St
West Stockbridge, MA 01266

18. The Farmstead Creamery

535 Summer St, Lee, MA 01238
Cones of ice cream splayed on a wooden surface
A variety of cones.
The Farmstead Creamery

Join the Jersey cows strolling the fields and taking in the views at this farm and ice cream shop in Lee. Located at High Lawn Farm, the Farmstead Creamery serves flavors like sweet cream, chocolate chip, and purple cow (black raspberry ice cream with white and black chocolate chips). You can stock up on Berkshire provisions at the same time, including cheeses, meats, preserves, pickles, and maple syrup. If you’d prefer savory to sweet snacks, order a cheese and charcuterie platter featuring the dairy’s cheese and local accouterments, and find some seats among the picnic tables outside.

535 Summer St
Lee, MA 01238

19. Alpamayo Peruvian Cuisine

60 Main St, Lee, MA 01238
A plate of various types of fried seafood
Fried seafood platter.
Alpamayo Peruvian Cuisine

Alpamayo has been a local favorite in downtown Lee since 2010, offering Peruvian classics such as lomo saltado and ceviche. Chef Javier Fernandez, who owns the place with his wife, Alicia, was an award-winning bartender, so definitely don’t pass on the cocktail menu, which includes a stunning pisco sour and refreshing chilcano (pisco, ginger beer, lime). 

60 Main St
Lee, MA 01238

20. The Lost Lamb

31 Main St, Stockbridge, MA 01262