Live music
People come into our tavern and say they first played in it fifty years ago. The Berkshires have a rich musical tradition, we’re a little part of it! James Taylor played on the lawn in the summer of 1970; Randy Weston would play here; Arlo Guthrie has come through; there’s a rumor that Bob Dylan was once in attendance. We have a groovy poster from when “Stephanie” played here when it was Alice’s. Johnny Irion revitalized the program a few years ago, and now we generally have a show every night the bar is open.
Upcoming shows
Colby Lewis & Steve Ide
A beloved Berkshire duo, Colby Lewis and Steve Ide bring timeless songs from the ’60s, ’70s, and beyond to life with rich harmonies, soulful guitar, and easy charm. Their performances blend classic favorites with heartfelt musicianship, creating the perfect soundtrack for an evening in the Ostrich Room.
Two Acts! Barbara Stein + The Weird Birds
Join us for two incredible acts! Barbara Stein, and The Weird Birds
Barbara Stein's soulful vocals and masterful guitar work blend alt-rock and Americana blues. Known for her heartfelt originals and fresh takes on familiar songs, Barbara brings warmth, artistry, and a touch of storytelling to every performance—perfect for a cozy night of live music in the Ostrich Room.
The Weird Birds are an acoustic duo from Hillsdale, NY, who've been harmonizing together for over 15 years. Their sound blends soulful vocals with hauntingly uplifting melodies, drawing inspiration from Motown, Rock, Blues, Funk, and beyond. With a fresh twist on familiar favorites and heartfelt original songs, The Weird Birds create an intimate musical experience for anyone ready to listen and feel to.
Katherine Winston
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. Read more.
Andy Wrba & Friends
Andy Wrba & Friends is a dynamic collective led by bassist and bandleader Andy Wrba, known for his work with the Berkshire Jazz Collective. Each show brings together top local musicians for an eclectic mix of jazz, funk, folk, and more—delivering joyful, spontaneous performances that are never the same twice.
More upcoming shows
See Instagram for previews and updates. Email Jenny Rubin at jennyjrubin70@gmail.com for information about booking acts.