TOP 10 Cafes with live music in Stockbridge, Massachusetts

Cafe Adam, Bar and Restaurant is a charming establishment located at 420 Stockbridge Road in Great Barrington, Massachusetts. This versatile venue offers a cozy and inviting atmosphere perfect for enjoying a delicious meal, grabbing a drink at the bar, or even staying overnight in their comfortable lodging accommodations. The restaurant serves up a diverse menu featuring a range of culinary delights, from classic American dishes to international cuisine. Whether you're looking for a casual meal with friends or a romantic dinner for two, Cafe Adam has something for everyone. Come and experience exceptional hospitality and delectable fare at this hidden gem in the heart of the Berkshires.

Rio Cafe is a charming cafe and restaurant located at 403 Stockbridge Road in Great Barrington, Massachusetts. This cozy establishment offers a variety of delicious food options, including freshly brewed coffee, hearty breakfast dishes, scrumptious sandwiches, and delectable desserts. With a warm and inviting atmosphere, Rio Cafe is the perfect spot to relax and enjoy a meal with friends or family. Whether you're looking for a quick bite to eat or a leisurely dining experience, Rio Cafe has something for everyone to enjoy. Come visit us and experience the delicious flavors and friendly service that make Rio Cafe a beloved local favorite.

Barrington Brewery & Restaurant is a popular establishment located at 420 Stockbridge Road in Great Barrington, Massachusetts. This venue offers a unique combination of a brewery, bar, and restaurant, providing guests with a one-of-a-kind dining and drinking experience. The brewery produces a variety of craft beers that are served alongside delicious meals made from locally sourced ingredients. Whether you're looking to enjoy a casual drink with friends or indulge in a hearty meal, Barrington Brewery & Restaurant is the perfect destination for food and beer enthusiasts alike.

Xicohtencatl Restaurant, located at 50 Stockbridge Road in Great Barrington, Massachusetts, is a hidden gem offering authentic Mexican cuisine in the heart of the Berkshires. Known for its flavorful dishes and warm hospitality, Xicohtencatl is a must-visit for anyone craving a taste of Mexico. Chef Angel's mole, a special family recipe passed down through generations, is a standout dish that has garnered national attention, even being featured on Food Network's Emeril Live! Whether you're in the mood for something spicy or savory, Xicohtencatl's menu has something for everyone. Come experience the flavors of Mexico at Xicohtencatl Restaurant.

The Backstage Grille is a cozy restaurant located at 109 Stockbridge Road in Great Barrington, Massachusetts. Offering delicious food options for dine-in or carry-out, with the convenience of curbside pickup available. The restaurant's regular hours are Monday-Thursday from 5pm-10pm, Friday from 4pm-midnight, Saturday from noon-midnight, and Sunday from noon-10pm. Situated inside Cove Lanes, The Backstage Grille is the perfect spot to enjoy a meal with friends and family. Contact them at 413-717-8804 for more information.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.