Events

Brian Mitchell & Friends — Live at Pearl Moon Friday, December 26 • 9:30–11:30 PM

Get ready for a true musical gumbo as Brian Mitchell & Friends cook up a spicy blend of blues, rock, and funky New Orleans–style R&B.

A five-time Grammy Award–winning artist, Brian Mitchell has brought his unmistakable sound to stages with Levon Helm, Bob Dylan, Bruce Springsteen, Little Feat, and Dolly Parton. Closer to home, he’s a fixture in the Woodstock scene, performing regularly with The Weight Band and The Helm Family Midnight Ramble.

Join us at Pearl Moon for a holiday-season throwdown filled with soul, swagger, and that unmistakable New Orleans groove.  This is our holiday gift to you; no tickets needed for the Dec 26 late night show—just come enjoy the music!

✨ Boreal – Bossa Nova Dinner Show Friday, December 27 · 7:30–10pm Pearl Moon, Woodstock

Transport yourself to the sun-soaked rhythms of Brazil with Boreal, a band bringing the smooth, sophisticated sounds of Bossa Nova to Pearl Moon. Their elegant melodies, intricate harmonies, and gentle, swaying grooves create the perfect backdrop for a relaxed, intimate evening.

Settle in for dinner, sip on your favorite drinks, and let Boreal’s lush, breezy music carry you away to a world of warm rhythms and timeless Brazilian charm.

✨ Jay Collins Gravy Train – Jazz Brunch Sunday, December 28 · 11am–2pm Pearl Moon, Woodstock

Ease into your Sunday with the soulful, upbeat sounds of Jay Collins Gravy Train at our Live Jazz Brunch. Led by the accomplished Jay Collins, whose career spans touring with the Gregg Allman Band, arranging horns for Little Feat, and Grammy-winning work with the Levon Helm Band, this ensemble brings infectious energy and masterful musicianship to every performance.

Settle in for a delicious brunch, enjoy lively jazz melodies, and let the warm, expressive sounds of Jay Collins and his band lift your spirits and get your toes tapping. A perfect Sunday blend of great food, music, and good vibes.

✨ Henry Ferland Trio – Acoustic Jazz Dinner Show Monday, December 29 · 6–8pm Pearl Moon, Woodstock

Close out the year with an intimate evening of extraordinary musicianship as Henry Ferland Trio brings their masterful fingerstyle guitar, rich harmonies, and dynamic interplay to Pearl Moon.

Known for blending melody, rhythm, bass, and percussion simultaneously, Henry’s performances are a mesmerizing mix of technical brilliance and heartfelt expression. Alongside his trio, he delivers a captivating experience that fuses Americana, jazz, and original compositions into an unforgettable dinner show.

Join us for great food, glowing vibes, and an evening of virtuoso music to celebrate the season.

✨ Triad – Acoustic Dinner Show Tuesday, December 30 · 6–8pm Pearl Moon, Woodstock

Wind down your year with the warm, harmony-rich sound of Triad at Pearl Moon. This acoustic folk trio blends heartfelt songwriting, lush vocals, and an organic, intimate style, creating a cozy atmosphere perfect for a relaxed dinner evening.

Their set moves effortlessly between soulful originals and reimagined folk favorites, inviting you to hum along, tap your feet, and soak in the rich, comforting tones of live acoustic music.

Settle in for great food, glowing vibes, and a soothing end-of-year musical experience.

✨ Strangehouse Presents: Nighthawks – Roaring 20s Masquerade NYE Party Tuesday, December 31 · 10pm–1am Pearl Moon, Woodstock

Step into the glamour, mystery, and mischief of the Roaring 20s with Strangehouse Presents: Nighthawks, a New Year’s Eve masquerade like no other. Spin through the decades with DJ Tryst, who’ll keep the dance floor alive spinning through the decades! A journey of music that moves through time and mood!

Dress to dazzle in masks, feathers, and flapper chic, and immerse yourself in an atmosphere of good vibes, moody glamour, and playful decadence. Explore mystical corners with tarot readings and browse unique vendors from Strange Love Shop, offering curiosities and delights to spark your imagination.

Join us at Pearl Moon, Woodstock, for a night of dancing, enchantment, and celebration — ringing in the new year in style, intrigue, and magic.

10pm–1am | Masks encouraged | Good vibes guaranteed

LIVE ON AIR STREAM WITH 98.1 WKZE

DJ Tryst is a sonic shapeshifter who moves effortlessly between decades and dance floors. She’s the force behind some of Woodstock’s and Hudson Valley's most beloved themed parties — from the sweat-slicked, mirror-ball magic of Inferno Disco Funk, to the neon-soaked nostalgia trip of Nightwave: 80s Dance Party.

On top of lighting up the late-night crowd, she also hosts Nighthawks Radio, where her curated blends, deep cuts, and after-dark musings guide listeners through the witching hours.

A mood-maker, a vibe-builder, and a nightlife storyteller — DJ Tryst is where rhythm meets ritual.

Follow

instagram.com/tryst_official