- by Allyson Brady
MUSIC IN THE BERKSHIRES
The Berkshires, nestled in the scenic hills of Western Massachusetts, are one of New England’s most unexpected music destinations—especially in the summertime. Whether you’re road-tripping with friends or seeking a solo escape, you’ll find unforgettable performances in charming venues and under wide, starlit skies.
From soothing symphonies to boot-stomping country, there’s something here for every kind of music lover. So, grab a blanket, pack your sense of rhythm, and head out for a laid-back adventure filled with soulful tunes and an unforgettable atmosphere.
Music Venues in the Berkshires
Tanglewood – Lenox, MA
During the summer months, this picturesque outdoor venue is the home to the Boston Symphony Orchestra. Along with frequent appearances from the orchestra, Tanglewood offers a variety of music genres and artists, all in a gorgeous setting. This summer, Tanglewood is hosting Lynyrd Skynyrd, Yo-Yo MA, and a special performance of Star Wars: Return of the Jedi by the Boston Pops!
Mahaiwe Performing Arts Center – Great Barrington, MA
For those who enjoy musicals and classic performances, this historical performing arts center offers live music, theater, and film events all year. Their Summer 2025 lineup includes a performance of the timeless musical, Singin’ in the Rain, singer-songwriter Rosanne Cash, and the Berkshire Opera Festival.
The Egremont Barn – South Egremont, MA
This rustic venue is known for its cozy atmosphere and mix of live music, from folk to indie rock, often featuring up-and-coming artists. Stop by this summer for weekly open mics, local bands, and tribute acts of musical icons such as Bob Marley and Led Zepplin.
The Lion’s Den at Red Lion Inn– Stockbridge, MA
Described as “the sound of soul of the Berkshires since 1937”, this unique venue offers intimate, speak-easy vibes with jazz music and bluesy tunes. Along with great music, you’ll also find an impressive food and cocktail program, highlight locally crafted flavors.
Bousquet Mountain – Pittsfield, MA
As the name suggests, this outdoor venue offers gorgeous mountain views all under the stars. Grab your lawn chairs or blankets and join in at Bousquet’s several music festivals held throughout the summer.
MASS MoCA – North Adams, MA
This iconic art museum hosts live music events year-round, and they have quite the summer season planned! From a weekend long festival to a contemporary acapella group, MASS MoCA is showing a variety of unique artists in the coming weeks. Additionally, every Thursday from early July to early September, you can enjoy free live music at The Chalet, a riverside beer garden and sculpture space.
Upcoming Concerts and Festivals in the Berkshires
The Chalet at MASS MoCA – North Adams, MA
July 3rdrd – September 4th, 2025
The Chalet at MASS MoCA returns for Summer 2025 with a free riverside beer garden and live performances under the stars. Running ever Thursday evening throughout the season, the series features a vibrant lineup including DJs, drag shows, dance, staff performances, and community nights, offering unforgettable summer experiences.
LOUD Weekend – North Adams, MA
July 31st– August 2nd, 2025
Also located at MASS MoCA, the 2025 LOUD Weekend Music Festival offers a wide variety of adventurous music, all while exploring the museum exhibits, indoor and outdoor!
Bousquett Jazz Festival – Pittsfield, MA
August 16th, 2025
Experience the VERY FIRST Bousquet Jazz Festival, a vibrant summer celebration of jazz featuring stunning views, great food and drinks, and live performances by local jazz talent! Enjoy artists including Rob Putnam’s Good Vibes Organ Trio, Michael Benedict and Bopitude, Svetlana and the Delancey Five, and the Peggy Stern Trio in a laid-back mountain atmosphere.
Summer Stomp Country Festival – Pittsfield, MA
August 2nd, 2025
Get ready for a boot-stompin’ celebration of country music at the Summer Stomp Country Music Festival, part of the Bousquet Summer Concert Series at beautiful Bousquet Mountain. Enjoy a high-energy evening of live music and line dancing with performances by Whiskey City, Colby Robb, Lindsay Anne, and The Hotshot Hillbillies.
Groove Your Way into a New Home
Have the rhythms of the Berkshires convinced you to move? (and we don’t mean dancing!) If you want to make the Berkshires of Massachusetts your home, our Lamacchia Realty Berkshire REALTORS® are here with the local expertise to help you find the perfect place.
