It may be October, but it still feels like summer — not just because of the weather but also because of the vibrant energy of Berkshire County’s live music scene. This week features 45 performances covering jazz, rock, pop, soul, R&B, hip-hop, rap, bluegrass, and the American Songbook. From intimate club shows to large-stage concerts, there’s something for everyone. Check out a few highlights below—and don’t forget to review the full schedule to plan your next musical outing.
This week, we start by highlighting the incredible number of local favorites playing in the region, including Colby Lewis & Steve Ide, Whistle and The Stack, Benny Kohn Trio, Andy Wrba & Friends, Chantell, Wanda Houston, Aimee Van Dyne, Hot Sauce, Natalia Bernal, and Rounders Revival. In addition to these local favorites, consider these highlighted shows:
- Banjo Basecamp Faculty Concert at Studio 9 on Wednesday. Hosted by GRAMMY-winning banjoist Alison Brown, who has assembled an all-female faculty that includes the 6-time IBMA award-winning banjoist and Steve Martin Banjo Prize (SMBP) winner Kristin Scott Benson and SMBP winner BB Bowness.
- Thursday represents a conundrum for Grateful Dead fans, with two tribute bands playing in the county: Steal Your Space – GRATEFUL BRO at The Stationery Factory and Shakedown Citi at The Egremont Barn. Dead Heads, start your engines!
- TLI Jazz: Berkshires Jazz 20th Anniversary Celebration with Emmet Cohen and special guest vocalist Georgia Heers at Tanglewood on Friday (Sold Out). Cohen, recognized as DownBeat Magazine’s Rising Star artist of 2024, brings his trio along with guest vocalist Georgia Heers to celebrate Berkshires Jazz’s twenty years of delivering world-class jazz to the region.
- DJ Lucas and Jackson Whalan at Barrington Hall at Crissey Farm on Saturday. Music returns to Crissey Farm! It’s an exciting night of rap and hip-hop featuring DJ Lucas, Jackson Whalan, Finesse Fresco, Harlow Road, and Buddha the Great.
- Ann Hampton Callaway at the Indigo Room at Mahaiwe on Saturday. It’s Grand Opening Weekend at the Indigo Room! Don’t miss the Tony-nominated singer-songwriter, who will perform highlights from her hit shows The Streisand Songbook, Ann Hampton Callaway Sings the ‘70s, The Linda Ronstadt Songbook, To Ella with Love, From Sassy to Divine: The Sarah Vaughan Project, and Finding Beauty: Inspired Classics and Originals.
- Milton at Dream Away Lodge on Saturday. Out of New York City, Milton is one of our favorite visiting artists and one of the first musicians we interviewed here at MITB.
- Francis Aud – FONK™ MUSIC at The Egremont Barn on Sunday. Aud is known for creating his own brand of FONK™ MUSIC—a high-energy blend of funk and pop that’s equal parts groove and good vibes.
- Guy Davis at the Indigo Room at Mahaiwe on Sunday. Continuing the Grand Opening Weekend at the Indigo Room, Guy Davis is a two-time Grammy nominee for Best Traditional Blues, as well as a musician, actor, author, and songwriter.
- Chuwi (pictured above) at MASS MoCA on Sunday. The genre-blending Puerto Rican group combines elements of plena, indie, and Caribbean rhythms. Chuwi’s collaboration with Bad Bunny on the track “WELTiTA” has helped boost the band’s popularity.
You can learn more about all of these performances in our day-by-day show rundown below, or jump right to our music calendar. Use the subscribe button below to receive this free weekly rundown of upcoming performances in your inbox each Monday.
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8:00 pm – 11:00 pm Milton @ Dream Away Lodge, Becket.
Sunday
11:30 am – 12:00 pm Terry A La Berry @ Mahaiwe, Great Barrington.
12:00 pm Sound Art 2 Experimental Music Festival @ WBCR-lp Studio, Great Barrington.
1:00 pm – 4:00 pm The Honig Brothers @ portaVia, Dalton.
2:00 pm – 5:00 pm Jason & Trev Acoustic @ Balderdash Cellars, Richmond.
3:00 pm – 5:00 pm Mr. Dan the Melody Man (Kids Music) Free Show @ Egremont Barn, South Egremont.
5:00 pm Les Chrostowski @ Route 8 Pub, Becket.
6:30 pm – 9:30 pm Michael Junkins Trio @ The Lion's Den, Stockbridge.
7:00 pm – 9:00 pm colin mcgrath @ Dream Away Lodge, Becket.
7:00 pm Silver Lake Presents @ Hot Plate Brewing Co, Pittsfield.
7:00 pm – 9:30 pm Francis Aud – FONK™ MUSIC @ Egremont Barn, South Egremont.
8:00 pm Guy Davis @ Mahaiwe, Great Barrington.
8:00 pm Chuwi @ MASS MoCA, North Adams.
8:00 pm – 10:00 pm Fall Music Series-Greg Caproni @ Jiminy Peak Mountain Resort, Hancock.
Please get out and support your local musicians and venues!
— Mark @ Music in the Berkshires