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
The Wolves
The Wolves, led by Kara Wolf on vocals and Darby Wolf on keys, bring together some of the Berkshires’ top local musicians. Their setlist spans everything from classic ’60s hits to modern favorites, creating an upbeat, feel-good sound.

Evan Lanoue Band
An independent singer-songwriter and musician from Berkshire, MA, discovered his passion for music at a young age by mastering his favorite Beatles melodies on the piano. Mixing elements of pop and classic rock blues, he crafts soulful and introspective songs that carve out a unique genre. With support from G Winnard on the drums and Dan Esko on the bass, their performances resonate with dynamic energy and depth.

Speakeasy Soiree: MaryAnn Palermo Jazz Trio
Join us for live jazz featuring the Mary Ann Palermo Jazz Trio, prohibition-inspired cocktails, and the thrill of the Roaring ’20s.Your night out supports HomeFarm's work of restoring the historic farm, saving animals, and transforming lives through animal-assisted programs.
Your ticket includes a welcoming cocktail, hors d'oeuvres, and a fun night of live music, dancing, some Prohibition trivia, raffles, silent auction and more! Cash bar.

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.

More upcoming shows
October 2025
November 2025
See Instagram for previews and updates. Email Jenny Rubin at jennyjrubin70@gmail.com for information about booking acts.