The Ostrich Room at Apple Tree Inn 10 Richmond Mountain Rd., Lenox appletreeinnlenox. com 413-637-1910
This warm and inviting live music venue is a blend of history, hospitality, and a vibrant music scene. Originally a jazz hotspot, it was later owned by Alice Brock( of Alice ' s Restaurant fame) under the name Alice ' s at Avaloch. It’ s within walking distance of Tanglewood and Kripalu. With a carefully curated lineup featuring jazz on Thursdays and a blend of folk, rock, bluegrass, and soul on weekends, the Ostrich Room provides a 50-seat setting where music lovers of all ages come together. Jenny Rubin, co-owner and operator of The Egremont Barn( currently closed but hoping to reopen), is booking the acts by tapping into her extensive network of talented musicians. The cozy, wood-paneled tavern offers an elevated Mediterranean-inspired menu, handcrafted cocktails, and a welcoming, house-party vibe. Outdoor seating and pre-Tanglewood music under the lights are featured in the summer. Local music enthusiasts Isabel Rose and Steve Stern appreciate what Apple Tree’ s new owner, Claire Collery, has accomplished with the property since it reopened in June 2024.“ Claire is lovely and really wants to share her inn with our community. The Ostrich Room has a great feel for music events, and the food and service don’ t disappoint!” All events are free; arrive early for a good table. Upcoming performances include Rounders Revival( May 2), the Camellia Trio( May 16), the Evan Lanoue Trio( May 22), Wanda Houston( May 23), and the Andy Wrba Trio( May 31).
The Dream Away Lodge 1342 County Rd., Becket thedreamawaylodge. com 413-623-8725
Tucked away on October Mountain, this legendary restaurant, bar, and music venue is housed in a 200-year-old farmhouse. Steeped in history and folklore— Dylan famously stayed here during the Rolling Thunder Revue tour— The Dream Away has been a cornerstone of the Berkshire music scene since 1947. Rooted in folk and singer-songwriter traditions, it also welcomes country, jazz, blues, indie rock, and world music. The cozy and historic music room, which holds up to 40 guests, fosters an up-close connection between artists and audiences, while the adjacent restaurant and bar provide a welcoming space for music lovers of all generations. All events are free; early arrival is recommended for a spot in the music room.“ We enjoy so much incredible talent within its humble walls,” says Cynthia Fletcher, a music lover from Otis.“ The artists are so close that you can see exactly how Bobby Sweet coaxes his guitar, or Milton indulges his wry smile, or Billy Keane floats a new perspective on fresh flowers.” Co-owner Dan Giddings, who books the performers, is still finalizing the calendar for May and June, but listed performances include Dan Blakeslee( April 26), 5 Pound Horse( May 2 and June 14), Milton( May 10), Stomp Box Trio( May 16), Glori Wilder & The Moonflowers( May 30), Lisa Michelle Anderson( June 6), and Avi Jacob( June 19).
The Foundry 2 Harris St., West Stockbridge thefoundryws. com 413-232-5222
The Foundry in West Stockbridge is a dynamic, multidisciplinary performing arts venue dedicated to amplifying underrepresented voices and fostering community through live performances. Since opening in 2019, this intimate 80-seat venue has built a reputation for presenting an eclectic mix of original music, from folk and indie singer-songwriters to classical ensembles, jazz, blues, Celtic, Quebecois, and experimental artists. The Foundry prioritizes unique and emerging talent over cover and tribute bands, offering audiences a fresh and diverse listening experience. Loyal patrons appreciate the venue’ s inclusive and welcoming atmosphere, actively engaging LGBTQ + and BIPOC communities through collaborations with local organizations. A true listening room, music lovers appreciate The Foundry’ s excellent acoustics. They can grab beverages at the bar at the rear of the venue. Tickets are general admission. Upcoming performances include the Itay Dayan Quartet( May 8), Cantrip( May 18), Namoli Brennet( June 7), and Sean Dagher( June 25). See page 57 for more at The Foundry.
The Guthrie Center 2 Van Deusenville Rd., Great Barrington guthriecenter. org 413-528-1955
The Guthrie Center is more than just a music venue— it’ s a cultural and community hub dedicated to artistic expression, education, and outreach. Housed in the historic Old Trinity Church in Great Barrington, the center fosters an intimate concert experience unlike any other in the Berkshires. Its renowned Troubadour Series, running from Memorial Day through Labor Day, has been a staple for over 20 years, showcasing a thoughtfully curated lineup of both national and local artists across various genres. While rooted in folk traditions, the Guthrie Center embraces a diverse range of musical styles, delivering unique performances to its loyal audience. With a cozy, up-close atmosphere, each show fosters a special connection between artist and listener. Given its 92-seat capacity, performances often sell out, making early ticket purchases or membership benefits highly recommended. Upcoming performances include Chris Smither( May 31), Cole Quest & The City Pickers( June 14), and Joe Crookston( June 21).
Knox Trail Inn 1898 E Otis Rd., East Otis theknoxtrailinn. com 413-269-4400
This historic inn and lively music venue is celebrated for its inviting atmosphere, American comfort food, and vibrant weekend performances. Featuring an elevated stage, a spacious dance floor, and thoughtfully designed acoustics, The Knox offers an exceptional experience for both musicians and audiences. Hosting live music since the 1960s, this 150-seat venue features bands from across New England, providing an eclectic mix of classic rock, country, folk / Americana, blues, and energizing’ 80s hair bands. Located near Otis Reservoir— the largest recreational lake in Massachusetts— the venue sees a surge of visitors in the summer, making reservations highly recommended on music nights. All events are free. Upcoming performances include local favorite bands like Liquid Courage( May 3), Rumours( May 10), Rock 201( May 17), Generation X( May 24), The General Gist( May 31), D-Rod and the Uprising( June 7), Full Burn( June 14), and Even It Up( June 21).
The Lion’ s Den at Red Lion Inn 30 Main St., Stockbridge redlioninn. com / the-lions-den 413-298-1654
This historic speakeasy-style music venue offers
May Holiday / June 2023 2025 BERKSHIRE MAGAZINE // // 39