Exquisite fireside brunch and fun improvisational music by Diana Herold and her Unsung Heroes.

The Wanda Houston Project is a dynamic quartet bringing the music of the 30s through the 70s... Rhythm, blues, jazz, and soul!

Jazz brunch continues with Berkshire Jazz Blues & Soul legend Bobby MacVeety. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

One-time opportunity to view and purchase Saadia Shaza’s one-of-a-kind, hand-dyed Autumnal dress collection.

Join us at Trailhead Berkshires for a delicious brunch with music from bassist Tarik Shah.

Jazz Brunch continues with the Luke Franco Trio! This is the meanest Jazz Trio around. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

Jazz brunch continues with Berkshire Jazz Blues & Soul legend Bobby MacVeety. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

Jazz brunch continues with Pamela Knowles. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

Join us at Trailhead Berkshires on Sunday, September 14th for delicious food and great music with the Good Vibes Organ Trio.

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

Join us at Trailhead Berkshires for a delicious brunch with music from bassist Tarik Shah.

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

Cozy fireside brunch with live jazz by The Michael Junkins Trio.

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

Jazz brunch continues with Berkshire Jazz Blues & Soul legend Bobby MacVeety. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

A full-hearted experience of original Jamaican Rock Steady style Reggae rooted in rhythm, history, and spirit.

Every Wednesday, Rain or Shine! Community fun and casual food for all ages. Pool, Fire, Games, Dancing, Tacos, Burgers, S’mores.

Monthly gathering remembering the legendary concert venue & community hub throughout the 50s, 60s, and 70s.B ring your stories and enjoy the amazing food and drink at Race Brook’s Trailhead Berkshires pop up restaurant!

Every Wednesday! Community fun and casual food for all ages, featuring music from Brooklyn based Deejay Theory.

Jazz Brunch continues with the Luke Franco Trio! This is the meanest Jazz Trio around. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

Qi Gong in the Backyard with Corey Chapman

Every Wednesday! Community fun and casual food for all ages.

Jazz brunch continues with Chad McLoughlin and his trio. Enjoy food from the new Trailhead Berkshires pop-up restaurant!

Qi Gong in the Backyard with Corey Chapman

Come sing your heart out at Karaoke night in the Trailhead Lounge. 6-9pm on July 18th

Reggae Wednesday Pool Club with Digital Ancient Dub.