15 Must-Try Restaurants in the Berkshires

Founded in 1917 as a five-cent hot dog stall for mill workers heading home, Jack’s Hot Dog Stand has been serving up burgers, hot dogs, and hand-cut fries in its cozy downtown North Adams spot ever since. The lively servers expertly steam, fry, assemble, and wrap your meal right before your eyes, a testament to decades of tradition. Stepping inside feels like a trip back in time. While you can no longer snag a hot dog for a nickel, now priced at $2, the charm of this historic stand remains intact.

Executive chef and co-owner Nicholas Moulton gained recognition on Food Network’s Guy’s Grocery Games in 2019, where Guy Fieri dubbed him the “veggie king.” This title is especially fitting at Mezze, where Moulton curates a modern farm-to-table menu. Seasonal dishes may include miso-marinated bistro steak accompanied by roasted onion and delicata squash jam, scallion pancakes with lacinato kale, or petite butternut squash served with beluga lentils, hen-of-the-woods mushrooms, and fermented squash-seed curry.

Dottie’s Coffee Lounge serves strong brews in a vibrant setting. Housed in a historic building on the lively North Street of downtown Pittsfield, this cozy spot boasts white brick walls and industrial lighting, creating a rustic, bohemian ambiance. The menu features inventive takes on classics, such as a grilled cheese fried in ghee and a barbecue pulled pork burrito topped with fire cider slaw. Don't miss live music during Domingo Brunch on Sundays, but arrive early—lines can stretch out the door in summer.

After Dottie’s closes for the day, step next door to Dorothy’s Estaminet for happy hour and a more refined menu. This elegant counterpart offers shared platters called “Experiences,” with options to add protein or rice croquettes. Enjoy seasonal and classic cocktails crafted with the same care as the espresso drinks next door.

Just across from Espetinho, Brazzucas Marketplace offers a delightful array of pantry essentials, drinks, and sweets from Brazil, Latin America’s largest nation. Owners Fabia Raquel Atherton and Nazira Vargas marked their grand opening in Summer 2024 with live music and samba dancing. While primarily a grocery store, there’s a small kitchen serving Brazilian specialties like risoles camarão (shrimp-filled fried turnovers) and cachorro quente, a hot dog simmered in tomato sauce and garnished with parmesan, veggies, and hard-boiled quail eggs. Don't forget to sample their decadent desserts, like the classic chocolate flan known as brigadeirao. If seating is scarce, grab your meal to-go and enjoy it in one of Pittsfield's parks.

Cristiane Melo began her culinary journey by taking orders through WhatsApp from friends in the local Brazilian community. Her flavorful cooking quickly gained popularity, leading her to establish a family restaurant in the heart of the Berkshires. Be sure to try the espetinhos (steak skewers) made from a cut of beef between the sirloin and rump. Don't miss the yuca fries and deep-fried salgadinhos—savory bites filled with cheese, beef, chicken, or sausage. Their desserts are also worth a taste, especially the mousses and churros. Keep an eye on their social media for specials like feijoada (Brazilian bean stew) or kibbeh.

Whether you’re returning from a performance at Shakespeare & Company in the summer or seeking a cozy spot on a winter night, Brava is the go-to late-night destination in Lenox. Open until 11:30 PM every night, it’s the ideal venue to share tapas or pizza with friends while sampling an extensive beer and wine list. The patatas bravas, a fried potato dish from which the restaurant takes its name, taste as if they’ve come straight from Barcelona and are absolutely essential.

Nowhere is the farm-to-table concept clearer than at Baldwin Farm, where you can see the pasture where your burger once grazed. Established in the mid-1800s, this family-run farm offers smash burgers, smoked chicken, and homemade hot dogs from their food truck and farmstand, just steps away from the pastures where they raise cows, chickens, pigs, and turkeys for Thanksgiving. Enjoy your meal at simple wooden picnic tables surrounded by the scenic views of the Berkshires’ rolling hills and quiet forests. Visit on a sunny day for lunch, or stop by the 24/7 store for fresh eggs, meats, local jams, and homemade salsa to take home.

Experience the charm of Jersey cows as they wander the fields at this delightful farm and ice cream shop in Lee. Nestled at High Lawn Farm, the Farmstead Creamery offers a range of flavors including sweet cream, chocolate chip, and purple cow (a mix of black raspberry ice cream with white and dark chocolate chips). You can also pick up local Berkshire goods such as cheeses, meats, preserves, pickles, and maple syrup. If you're in the mood for something savory, try a cheese and charcuterie platter featuring their cheeses alongside local accompaniments, and enjoy your meal at one of the outdoor picnic tables.

Since 2010, Alpamayo has been a beloved spot in downtown Lee, serving up traditional Peruvian dishes like lomo saltado and ceviche. Chef Javier Fernandez, an acclaimed bartender, showcases his talents with exceptional cocktails, including a delicious pisco sour and a refreshing chilcano (pisco, ginger beer, and lime).

Cozy and inviting like any Main Street Mytoury in downtown Stockbridge, The Lost Lamb also offers a delightful French touch, making you feel as if you’ve wandered into a tranquil Parisian street. With a background from Le Cordon Bleu, Claire Raposo is the creative force behind the artisanal breads, pastries, and decadent desserts, including her famed olive oil orange bundt cake. If you’re in the mood for something savory, the prosciutto and gruyere sandwich on a housemade baguette is a must-try.

The Berkshires are home to many excellent bakeries, charming cafes, and upscale pizza spots, but none rival the Berkshire Mountain Bakery. Located in Housatonic within a historic paper mill along the river, this bakery produces hundreds of loaves of bread and pizza crusts using traditional methods. Visit for fresh bread or pizza, available by the slice or as take-and-bake. Its Pittsfield location, situated twenty miles upstream, offers sandwiches, cheeses, and frozen items. Remember to call ahead or drop by outside of peak hours for the best experience.

After nearly twenty years of operating a traditional restaurant, this family pivoted to create a counter-service lunch venue that doubles as the only Asian market in the county. Indulge in classic ramen varieties or try vegan options like tantan or kimchi ramen. If ramen doesn’t strike your fancy, they also offer sushi and poke. Don’t forget to treat yourself to some mochi from the freezer or pick up a package of “x2 Spicy Buldak” ramen for later enjoyment.

At the Prairie Whale, owner Mark Firth, known for his work at Brooklyn’s Diner, Bonita, and Marlow & Sons, alongside chef Stephen Browning, puts a contemporary spin on classic dishes like pig head rillettes and brick chicken. Seasonal specials showcase the finest ingredients sourced from a growing network of local farms. Choose to sit at the bar, a cozy table, or on a communal bench for a welcoming dining experience.

This seasonal roadside burger and sandwich spot, the Bistro Box, serves up inventive and tasty sandwiches made from fresh, seasonal ingredients. You can’t miss the roadside burger or the farm frank, a local no-nitrate hot dog served with crispy french fries. Looking for something different to dip in? Try one of their rotating homemade fry sauces, featuring flavors like French onion aioli and hot honey. With a sprawling green lawn equipped with picnic tables, lawn games, and complimentary frisbees, it’s the ideal place for kids and dogs to play while you await your meal. Just remember to check the weather before heading out!

Since the 18th century, the charming Old Inn on the Green has attracted travelers along Route 57. Nestled in lush surroundings, the inn offers a rustic dining experience by candlelight. Enjoy your meal indoors at elegantly set tables with white linens under towering oak beams, or opt for a relaxed outdoor setting on the shaded garden terrace. Currently, the restaurant features a prix fixe menu priced at $65 per person.