Live music in Berkshire County, MA

Rev Tor marks three decades on The Colonial Theatre stage with a night centered on collaboration and musical history. Since 1996, the bandleader has been a steady presence on the East Coast club and festival circuit, traveling from Maine to Key West and sharing stages with members of The Grateful Dead, Dead & Co., Phish, The Allman Brothers Band and New Riders of the Purple Sage. Appearances alongside artists such as Leon Russell, Los Lobos and String Cheese Incident highlight a career known for technical prowess, soul and a generous, collaborative spirit. The anniversary jam features special guests and surprises throughout the show, including former members and musical friends, with an updated list of guests to be announced. General admission is $30, increasing to $40 on the day of the show. A portion of proceeds supports The Jake Galliher Foundation, which honors SSgt Jacob “Jake” M. Galliher by providing scholarships and awards to individuals who reflect his character, carrying forward a legacy of bravery, dedication and kindness.

Los Lonely Boys bring their Texican rock and roll to the Mahaiwe Performing Arts Center, with Lisa Morales opening. Brothers Henry, Jojo, and Ringo Garza shaped their sound in San Angelo, Texas, and reached a wide audience after their debut featuring the chart-topping single Heaven, which earned a Grammy, spent 76 weeks on the Billboard Top 200, and sold more than two million copies. Discovered by Willie Nelson’s nephew, they soon played Farm Aid and recorded with Willie, later collaborating with artists such as Carlos Santana while performing on major stages and supporting global causes. After a 2013 stage accident that sidelined Henry, the band doubled down on family and music, paused touring in 2019, then returned in 2022 with fresh momentum and even opened for The Who. Their 2024 album Resurrection on BMG blends their trademark style with soul and roots influences, energizing live audiences. Tickets are on sale now, priced from $34 to $69, with Mahaiwe member and youth discounts available.

Grammy award winner Madison Cunningham brings an evening of folk music to the Hunter Center, celebrating Ace, her newest album. The performance draws from a collection that follows the journey of heartbreak and renewal, moving from falling out of love to finding it again. Ace is her third release on Verve Forecast, co-produced with Robbie Lackritz, known for work with Feist, Rilo Kiley, Bahamas, and Peach Pit, and it spans fourteen tracks shaped with candor and heart. Arriving after the Grammy winning Revealer, this project emerged from a spell of writer’s block and shifts from observation to intensely personal storytelling. Cunningham set out to lead with feeling, crafting songs that are tender, lush, and brave. The first single, My Full Name, earned praise from PASTE for lyrics that balance breadth and intimacy, recalling the timeless quality of classical poetry. As co-producer, Cunningham brings piano to the forefront to create a sound that rises and resonates like a summit. The record is alive and richly textured, reflecting the vision she carried into the writing process, and she has shared that she loves every track.

Live buskers perform at the Great Barrington Farmers Market, offering street performances for market-goers.

Relive six decades of Cher’s biggest songs in a high-energy tribute starring Lisa Carter. She channels the unmistakable voice, attitude, and outsized glamour that define the legend, pairing soaring ballads and dance floor favorites with rapid costume changes, bold fashion, and plenty of glitz. A storytelling moment inspired by the iconic Farewell Tour adds an extra wink to fans. With a New York based band behind her, the show brings powerhouse vocals, big personality, and eye catching looks for a lively, bold, and fabulously over the top experience. Feathers, sequins, attitude, and unforgettable hits set the stage to believe in life after love all over again.