Six Spots for Live Music

If you’re reading this, you’ve probably already been to Tanglewood or experienced Berkshire Busk in Great Barrington. Berkshire County has been drawing music legends to its rolling hills for decades: James Taylor just played his 50th anniversary shows at Tanglewood on July 3 and 4! We’re here to share a handful of spots you can check out for a chill night in the mountains.

The Dream Away Lodge

1342 County Rd, Becket

Arlo Guthrie, Bob Dylan, Joan Baez and Allen Ginsberg are among the stars who have performed at Dream Away. While some may consider Becket off the beaten path, this cozy, quirky establishment with rich history is well worth the drive. It's a fantastic hangout spot with music and spoken word events from Wednesday - Sunday evenings.

Check out their packed calendar here!

Drifters Bar & Restaurant

101 Dan Fox Drive, Pittsfield

During the summer months, this restaurant at Bousquet Mountain offers disc golf, hiking and an awesome outdoor summer stage. Pop by for music on Friday evenings from 6 - 9 p.m. at Drifters or check out their summer concert lineup!

The Goldenrod Country Inn

144 Huntington Rd, Worthington

Okay, we know this isn't technically in Berkshire County, but the Goldenrod is really worth a visit. Opened in 2022, this inn has spectacular food, cocktails, AND live music! If you just need a great meal, stop here for dinner and make sure you get the fried brussels. Check out the event calendar on their website.

The Lion’s Den

30 Main Street, Stockbridge

The Lion’s Den at The Red Lion Inn has been around for nearly 100 years. They serve beer, wine, cocktails, and a straightforward menu of bar snacks. Come by for live music every Wednesday to Sunday from 7 - 10 p.m. and check out the schedule on their website. Be sure to bring your $10 cover!

The Ostrich Room 

10 Richmond Mountain Road, Lenox

Nestled in the historic Apple Tree Inn, we love The Ostrich Room for its seasonal outdoor menu, cocktails, and indoor and outdoor space to listen to some amazing local performers (see photo at right). Visit Wednesday and Saturday evenings from 7:30 - 9:30 p.m. Follow their Instagram to stay up-to-date with their schedule!

Starving Artist Creperie and Cafe

40 Main Street, Lee

Nightlife not your thing? No problem! Take a stroll on Main Street in Lee and pop into the Starving Artist for musical brunch on Sundays. From 11 a.m. - 2 p.m., you can enjoy live tunes with a delicious crepe, sandwich, salad, coffee or juice. Pro tip: Go with a friend and split a sweet crepe for dessert!

Where else do you love to go for live music? Let us know in the comments.