Katherine Winston in Persip Park

Persip Park 175 North St, Pittsfield, MA

From the rolling hills of New England, Katherine Winston is a Singer/Songwriter whose music is a blend of country, folk/rock, and pop. Inspired by musical icons like Stevie Nicks, Brandi Carlile, and Dolly Parton, Katherine’s powerhouse vocals and raw emotional power have captivated audiences all over the country and beyond. Katherine’s deeply relatable songwriting explores […]

Free

John Nalepa and Riverband Orchestra

Methuselah Bar & Lounge 391 North Street, Pittsfield, MA

Get your feet ready to tap to the infectious beat of this magnetic group!! Join us for a great night of live music with this dynamic and high energy musician and friends!! 🎶!!

Free

Jack Waldheim

Locker Room Sports Pub 232 Main St, Lee, MA

One Man Dance Band

Free

Chantell

Ostrich Room at Apple Tree Inn 10 Richmond Mountain Road, Lenox, MA

The Ostrich Room is thrilled to have Chantell and her band of seasoned musicians - legends in the Berkshires and beyond - performing everything from jazz, to funk, to blues, and more! She has brought her passion, energy, and talent everywhere - from the stage with Yoyo Ma, to performances with Broadway producers, and recently, […]

Free

Gold Crush

Egremont Barn 17 Main Street, South Egremont, MA

Gold Crush featuring Hannah Bracken is definiteky one to watch! The first show at The Barn was a hit! Come back and se them now!

$15

Sean Rowe Live at The Guthrie Center

Guthrie Center 2 Van Deusenville Rd, Great Barrington, MA

Sean Rowe is an American singer-songwriter, musician, recording artist, and forager. Rowe has a powerful sound with an emotional conviction that demands attention. NPR’s All Songs Considered says of Rowe’s vocals, “He can just crush granite with that voice. It’s so powerful.” The Wall Street Journal proclaimed, “Mr. Rowe's ringing baritone is as timeless as […]

$30 – $35

Jimmy Carpenter Band

The Stationery Factory 63 Flansburg Ave, Dalton, MA

Jimmy Carpenter, saxophonist, singer-songwriter, and arranger, began his musical journey over 35 years ago. In the ’80s, he toured the east coast with the renegade blues band, The Alka-Phonics, in the ’90s with the blues-rock band The Believers, with whom he learned about the music business. Over the years, Jimmy has toured internationally with Tinsley […]

$27.38

Lisa Michelle Anderson

Dream Away Lodge 1342 County Rd, Becket, MA

What happens when you are raised on the music of Dolly Parton in Southeast Kansas and Minnesota, move to Australia and learn to play the guitar? You get Lisa Michelle Anderson. Lisa's music has been described as "fresh linen and well-worn denim occasionally splashed with whiskey, beer, and hot sauce." Sam Otis Hill Lisa has […]

Free

Generation X Rock

Knox Trail Inn 1898 E Otis Rd, East Otis, MA

Grab a seat, order up some drinks and dinner, and settle in for an amazing show from GEN X ROCK! Paying tribute to the 80s & 90s in the Berkshires, Capital Region NY, VT, CT & beyond!

Free

Krishna Guthrie Band

Washington Town Park MA-8, Washington, MA

Rockin' Folkin' Blues Sunday afternoons at 4:00pm in the Washington Town Park, S Washington State Rd (Rte 8). Join in the family-friendly outdoor fun and help raise funds to improve the basketball court with the return of the 50/50 raffle! Donations also welcome. Returning this year: a free fairy garden activity. NEW this year: Local […]

Free

Scott Hirsch + Kelly McFarling

Tourists 915 State Rd, North Adams, MA

You’ve heard SCOTT HIRSCH’s work already even if you didn’t know it. He’s been the magic man behind so many records over the last couple decades-as producer, engineer, and multi-instrumentalist. He is the ‘other half’, the Yin to MC Taylor’s Yang in Hiss Golden Messenger and their previous group, The Court and Spark. He helmed […]

Free

Colby Lewis and Steve Ide

Ostrich Room at Apple Tree Inn 10 Richmond Mountain Road, Lenox, MA

The dynamic duo of Steve Ide and Colby Lewis are coming to The Ostrich Room, ready to play everything from classic rock, to country, to pop music! With guitars in hand, and a set described as the “Comfort Food for Our Generation”, Steve Ide and Colby Lewis will take our timeless tavern across genres and […]

Free

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