Events

✨ The Hardwoods – Acoustic Dinner Show Tuesday, December 17 · 6–8pm Pearl Moon, Woodstock

Unwind midweek with the warm, intimate sound of The Hardwoods. Their acoustic set blends heartfelt originals with thoughtfully reimagined favorites, creating a cozy, inviting atmosphere perfect for dinner at Pearl Moon.

With rich harmonies, melodic storytelling, and an organic, rootsy vibe, The Hardwoods deliver a soulful, relaxing evening of music that makes you feel right at home.

Settle in for good food, glowing vibes, and a night of authentic acoustic charm.

✨ Henry Ferland – Acoustic Dinner Show Friday, December 19 · 6:30–8:30pm Pearl Moon, Woodstock

Experience a night of extraordinary guitar mastery with Henry Ferland, a fingerstyle virtuoso who seamlessly blends melody, rhythm, bass, and percussion — often while singing — into a mesmerizing performance.

Henry’s expansive repertoire draws from Americana legends like Chet Atkins, Merle Travis, and Tommy Emmanuel, jazz greats such as Fats Waller, Duke Ellington, Jonathan Kreisberg, Julian Lage, and contemporary influences including Paul Simon and Dave Matthews, alongside his own original compositions. His performances are a captivating mix of technical brilliance and heartfelt expression that keep audiences coming back for more.

A Berklee College of Music graduate and Thumb-Picking Double Grand Champion, Henry has shared stages with Tommy Emmanuel, opened for Martin Taylor and Sean Rowe, and made his mark on the Hudson Valley scene both as a solo artist and with his electric jam band Stone House.

Join us for dinner and an intimate evening of virtuosic guitar, soulful melodies, and a performance that celebrates the power of music, resilience, and artistry.

✨ Trinoceros – Jazz Dinner Show Saturday, December 20 · 6:30–8:30pm Pearl Moon, Woodstock

Spend your Saturday evening immersed in the rich, dynamic sound of Trinoceros, a jazz ensemble known for their inventive improvisation, tight grooves, and soulful interplay. Their music blends contemporary jazz with classic influences, creating an engaging and deeply expressive experience.

Whether weaving through complex harmonies or settling into laid-back swing, Trinoceros delivers a performance that’s both sophisticated and accessible, perfect for a cozy dinner setting.

Join us for a night of exquisite jazz, warm vibes, and a memorable evening of music at Pearl Moon.

✨ Peter Einhorn – Christmas Jazz Brunch Sunday, December 21 · 11am–2pm Pearl Moon, Woodstock

Celebrate the holiday season with the smooth, soulful sounds of Peter Einhorn at our festive Christmas Jazz Brunch. A masterful guitarist and composer, Peter blends jazz sophistication with warm, melodic storytelling, creating the perfect soundtrack for a cozy Sunday morning.

Settle in with a delicious brunch, enjoy the seasonal tunes, and let Peter’s expressive playing fill the room with holiday cheer, improvisation, and joyous energy.

A perfect way to savor great food, great music, and the magic of the season.

Sunday, December 21 · 7–9PM · Pearl Moon Free Show — Canned Food Donations Strongly Encouraged

Join us for an evening of heartwarming holiday spirit as Pearl Moon hosts the Woodstock Holiday Hoot — a joyful gathering featuring performances from several of your favorite local musicians. Expect a magical mix of seasonal tunes, spirited collaborations, and the unmistakable charm that only Woodstock’s music community brings to the stage.

This year’s Hoot is hosted by Alex Castle and Charlie Thurman, guiding the night with humor, heart, and a whole lot of holiday groove.

✨ Admission is free, and we invite guests to bring a canned food donation to support our local community during this season of giving.

Come raise a glass, sing along, and celebrate the holidays with friends, neighbors, and the musicians who make this town sing. Festive vibes, great music, and holiday cheer await — see you at Pearl Moon!

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.

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