TOP 10 Cafes with live music in Pittsfield, Massachusetts

Electra's Cafe is a charming and cozy cafe located at 439 Pittsfield Road in Lenox, Massachusetts. Our cafe offers a welcoming atmosphere where customers can enjoy delicious food and beverages in a relaxed setting. Whether you're looking for a quick coffee to go or a leisurely meal with friends, Electra's Cafe has something for everyone. Our menu features a variety of freshly brewed coffees, teas, pastries, sandwiches, and salads made with locally sourced ingredients. Come visit us at Electra's Cafe for a delightful dining experience in the heart of Lenox.

Sportsman's Cafe Inc is a lively bar and night club located at 415 Pecks Road in Pittsfield, Massachusetts. With a welcoming atmosphere and friendly staff, this institution is a popular spot for locals and visitors alike to enjoy drinks, music, and good times. Whether you're looking to unwind after a long day or dance the night away, Sportsman's Cafe Inc has something for everyone. Come join us for a memorable night out in the heart of Pittsfield.

Crossroads Cafe is a cozy and inviting bar located in the heart of Pittsfield, Massachusetts. Situated at 195 Onota Street, this beloved institution offers a laid-back atmosphere where locals and visitors alike can enjoy a wide selection of drinks, delicious bar snacks, and live music. Whether you're looking for a place to unwind after work or catch up with friends on the weekend, Crossroads Cafe is the perfect spot to relax and enjoy good company. With its friendly staff and welcoming ambiance, it's no wonder that this bar is a favorite among the community.

Downtown Pittsfield, located at 33 Dunham Mall in Pittsfield, Massachusetts, is a vibrant cultural district known as the Upstreet Cultural District. This area is home to a variety of music, dance, theater, and community festivals, including the Colonial Theatre and Barrington Stage Company. The district also features public art, galleries, artist studios, and monthly art walks. Visitors can enjoy diverse cuisine from around the world at the district's restaurants and cafes, many of which offer live music. Local retailers in Downtown Pittsfield offer unique housewares, clothing, jewelry, and more. The district hosts events like Downtown Celebrates Spring Week and the Pittsfield Photo Challenge. Additionally, the Downtown Pittsfield App allows visitors to easily explore the area and take self-guided mural tours. With the support of donors and organizations like Berkshire Bank, Downtown Pittsfield continues to thrive and promote local businesses and artists.

Tavern At The A is a cozy and inviting bar and restaurant located at 303 Crane Avenue in Pittsfield, Massachusetts. Known for its delicious food and wide selection of drinks, this establishment is a popular spot for locals and visitors alike. The ambiance is warm and welcoming, making it the perfect place to relax and enjoy a meal or grab a drink with friends. Whether you're in the mood for a hearty meal or just looking to unwind with a cocktail, Tavern At The A has something for everyone. Come experience the friendly atmosphere and top-notch service at this beloved neighborhood spot.

Thistle & Mirth is a cozy and inviting bar and restaurant located at 44 West Street in Pittsfield, Massachusetts. This charming establishment offers a warm and welcoming atmosphere where guests can enjoy delicious food and drinks in a relaxed setting. With a menu featuring a variety of mouth-watering dishes and a wide selection of craft beers and cocktails, Thistle & Mirth is the perfect spot for a casual meal with friends or a night out on the town. Whether you're looking for a quick bite to eat or a leisurely dinner, this hidden gem in Pittsfield has something for everyone to enjoy.

Patrick's Pub is a cozy and inviting establishment located in the heart of Pittsfield, Massachusetts. Situated at 26 Bank Row, this popular bar and restaurant offers a welcoming atmosphere for locals and visitors alike. With a diverse menu featuring delicious food and refreshing drinks, Patrick's Pub is the perfect spot to unwind and enjoy a meal with friends or family. Whether you're looking for a casual lunch, a lively happy hour, or a relaxing dinner, this establishment has something for everyone. Come experience the warm hospitality and tasty offerings at Patrick's Pub today!

Angelina's is a charming institution located at 97 West Housatonic Street in Pittsfield, Massachusetts. This cozy spot offers a variety of delicious food options for takeout, dining in, or shopping in their store. From freshly prepared meals to gourmet snacks and specialty items, Angelina's has something for everyone. Stop by and experience the warm atmosphere and mouthwatering flavors that make this establishment a favorite among locals and visitors alike.

Methuselah Bar and Lounge is a vibrant and stylish establishment located at 391 North Street in Pittsfield, Massachusetts. This multifaceted venue offers a unique blend of bar, food, night club, and restaurant experiences all under one roof. Whether you're looking to enjoy craft cocktails with friends, indulge in delicious gourmet cuisine, dance the night away to live music, or simply unwind in a chic and welcoming atmosphere, Methuselah Bar and Lounge has something for everyone. Come and experience the ultimate night out in Pittsfield at Methuselah Bar and Lounge.

Gallery Molloy is a unique and eclectic institution located at 115 Cheshire Road in Pittsfield, Massachusetts. This multifaceted establishment offers a diverse range of experiences, including an art gallery showcasing local and international artists, a trendy bar serving craft cocktails and artisanal beers, a boutique clothing store featuring stylish and one-of-a-kind pieces, a vibrant night club with live music and DJ sets, and a store selling a curated selection of home goods and gifts. Whether you're looking to admire beautiful artwork, enjoy a night out with friends, or shop for a special piece to add to your wardrobe or home, Gallery Molloy has something for everyone. Come and experience the vibrant atmosphere and creative energy of this one-of-a-kind institution in the heart of Pittsfield.

Peppes is a vibrant and energetic night club located at 46 Lenox Avenue in Pittsfield, Massachusetts. Known for its lively atmosphere, top-notch music, and fantastic drinks, Peppes is the perfect spot for a night out on the town. Whether you're looking to dance the night away with friends or enjoy a few cocktails in a stylish setting, Peppes has something for everyone. Come experience the excitement and fun that Peppes has to offer at this popular nightlife destination in the heart of Pittsfield.

Sideline Saloon is a lively bar located at 434 Fenn Street in Pittsfield, Massachusetts. Known for its welcoming atmosphere and friendly staff, this popular establishment offers a wide range of drinks, including craft beers, cocktails, and spirits. Guests can enjoy watching sports games on big-screen TVs, playing pool or darts, and socializing with friends. With regular live music events and special promotions, Sideline Saloon is the perfect spot for a fun night out in Pittsfield.