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.

Update: March 24, 2023: A-OK Berkshire Barbeque has closed.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Update: March 24, 2023: Nudel has closed.

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.

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). 

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.

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.

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.

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.

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.

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.

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.

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.

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.