Events

There's a particular kind of songwriter who knows how to let a story breathe. AJ Lipton is that kind of writer. Drawing from Bob Dylan, Karen Dalton, and Bobby Charles, the Austin-based artist creates folk and country songs that feel both timeless and lived-in.

Lipton's songs are built from real places—backstage rooms, long drives, kitchens at night. His writing moves at its own pace, favoring feel over flourish. Currently recording with Jim Weider of The Band in the Catskills, he typically performs with his group The Light Aluminum. Tonight's solo performance on acoustic guitar and piano strips everything down to what matters: the songs themselves.

This is songwriting as conversation. This is groove with a story to tell.  When AJ is on our stage, you'll hear exactly why.

Made up of some of the Hudson Valley’s most active and in-demand musicians, the Tillson Jazz Ensemble brings deep experience and easy chemistry to every performance. The group meets weekly to exchange ideas, shape new arrangements, and keep the music fresh — and that shared creative spirit comes through on stage.

Though each member has performed internationally, they’re deeply rooted in the Hudson Valley and love playing for their home community. Expect a relaxed, soulful brunch set filled with swing, groove, and effortless interplay — the perfect soundtrack for a slow, delicious Sunday.

Journey Blue Heaven & Rock City Riders (Craft and Pollard Sunshine) bring the authentic spirit of Woodstock to life. From the legendary fields of Bethel, NY to modern stages, their genre-bending originals and classic covers fuse the soulful sounds of the 60s and 70s with a contemporary edge. Winners of the Woodstock Film Festival’s Best International Video (2018), this is more than a performance—it’s a shared experience of music, love, hope, and community.

Pearl Moon Dinner Show Friday, January 9 | 6–8 PM

Pearl Moon’s 5-Year Anniversary Celebration marks five years of community, cuisine, and live music in the heart of Woodstock. Join us for a special evening featuring Boreal, whose lush bossa nova–inspired sound blends Brazilian rhythms with jazz and global influences. Smooth, intimate, and transportive, their live performance sets the perfect tone for a celebratory dinner experience filled with warmth, connection, and gratitude.

Pearl Moon Woodstock Dinner Show Saturday, January 10 | 6:00–8:30 PM

Saxophonist Jay Collins brings his signature warmth, groove, and deep musicality to this laid-back jazz brunch. A longtime presence on the New York and Hudson Valley music scenes, Collins has performed with artists ranging from Levon Helm to David Bromberg, blending jazz, soul, and roots influences with ease.

Joined by an easy-swinging ensemble, Jay sets the tone for a relaxed, soulful brunch — melodic, inviting, and full of feel. Perfect listening music to ease into your Sunday.

The Hardwoods bring a roots-forward acoustic sound shaped by folk tradition, close harmony, and honest storytelling. Their songs lean into melody and mood, drawing from Americana, old-time, and modern folk influences with a natural, unforced feel.

Perfect for a dinner setting, their music settles into the room with ease — thoughtful, melodic, and quietly engaging. An evening of well-crafted songs, rich harmonies, and acoustic warmth designed to complement good food and good company.

Tree of Life brings an unforgettable blend of R&B, funk, and jazz fusion to the stage, delivering rich grooves, soulful melodies, and masterful musicianship. Their sound weaves deep rhythm with improvisational flair, creating an immersive live experience that’s both relaxing and energizing. Perfectly paired with an evening of great food and atmosphere, this dinner show invites you to unwind, connect, and move to the music.

Pearl Moon Dinner Show Saturday, January 17 | 6–8 PM

Runs until Wednesday, February 11th, 2026

Pearl Moon will be taking a little winter rest from January 19 through February 11 — a chance for us to recharge, dream up new ideas, and get cozy before our next chapter of live music, great food, and beautiful nights together.

We’ll be back soon with fresh energy, new sounds, and lots of magic to share. Until then, stay warm, take care of each other, and we can’t wait to welcome you back in February 💫