TOP 30 Bar and grill outdoor dining in Pittsfield, Massachusetts

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Located at 303 Crane Avenue in Pittsfield, Massachusetts, Back Nine Bar & Grille is a cozy and welcoming bar that offers a laid-back atmosphere for patrons to relax and unwind. With a focus on providing delicious drinks and tasty food, this establishment is the perfect spot to catch up with friends or watch the big game. Whether you're looking to enjoy a cold beer, a handcrafted cocktail, or a hearty meal, Back Nine Bar & Grille has something for everyone. Come on down and experience the friendly service and great vibes for yourself!

Jae's 7 Winter is a cozy and inviting restaurant located at 7 Winter Street in the heart of Pittsfield, Massachusetts. Specializing in delicious comfort food and warm hospitality, this eatery offers a diverse menu of hearty dishes that are perfect for the winter season. Whether you're craving a steaming bowl of soup, a hearty sandwich, or a comforting plate of pasta, Jae's 7 Winter has something for everyone. Come in from the cold and enjoy a satisfying meal in a welcoming atmosphere at this charming establishment.

Old Man Jeff's Barbecue Company is a beloved food establishment located at 370 Pecks Road in Pittsfield, Massachusetts, United States. Known for its mouthwatering barbecue dishes, this restaurant offers a unique dining experience with both restaurant and counter service available. Open on Fridays and Saturdays from Noon until 8pm, or until they run out of barbecue, Old Man Jeff's is a popular spot for locals and visitors alike. Additionally, the restaurant offers catering services for events on any day of the week. Indulge in delicious barbecue fare at Old Man Jeff's Barbecue Company for a truly satisfying dining experience.