Events

✨ Santa Barbarians – Latin • Funk • Jazz Fusion Dinner Show Saturday, December 6 · 6:30–8:30pm Pearl Moon, Woodstock

Get ready for a high-energy, rhythm-forward night as the Santa Barbarians bring their electrifying fusion sound to Pearl Moon. This dynamic ensemble weaves together Latin grooves, funk fire, and jazz sophistication, creating a style that’s as vivid as it is undeniably dance-worthy.

Their set flows through vibrant original compositions, all infused with bold improvisation and tight, infectious rhythms — with reimagined jazz standards sprinkled throughout for a perfect touch of familiarity. The result? A rich, flavorful blend of styles that keeps the room buzzing and the night glowing.

Don’t miss this powerhouse group as they light up your Saturday dinner with color, groove, and irresistible musical chemistry.

✨ Tree of Life – R&B • Funk • Jazz Fusion Brunch Sunday, December 7 · 11am–2pm Pearl Moon, Woodstock

Let your Sunday unfold with deep groove and soulful energy as Tree of Life brings their vibrant blend of R&B, funk, and jazz fusion to our Live Brunch Series.

Anchored by Amit Shamir on drums and Mike Colletti on bass, the trio features the extraordinary Scott Brown on piano — a seasoned musician whose résumé spans performances with legends including Roy Ayers, Jaco Pastorius, Luther Vandross, and many more. His rich musical history and masterful touch add a dynamic, expressive layer to the group’s sound.

Expect warm pocket grooves, lush harmonies, and improvisations that shimmer with soul — the perfect soundtrack to a cozy, delicious Sunday at Pearl Moon.

Join us for brunch, community, and a morning filled with world-class musicianship.

✨ Journey Blue Heaven & Rock City Riders – Woodstock Spirit Dinner Show Wednesday, December 10 · 6–8pm Pearl Moon, Woodstock

Immerse yourself in the true Woodstock spirit as Journey Blue Heaven & Rock City Riders (Craft and Pollard Sunshine) bring their uplifting, genre-blending sound to Pearl Moon. From the fields of Bethel to today’s stages, their music fuses 60s/70s vibes with a fresh modern edge — heartfelt, hopeful, and irresistibly soulful.

Expect a vibrant mix of originals and reimagined classics, all delivered with the warmth, freedom, and community energy that define the Woodstock legacy. Winners of the Woodstock Film Festival’s Best International Video (2018), this ensemble transforms every performance into a gathering of connection, joy, and shared groove.

This isn’t just a dinner show — it’s a love-filled, communal experience. Come be part of something extraordinary. 🌙✨

✨ Lali and the Pops – Dinner Show Friday, December 12 · 6:30–8:30pm Pearl Moon, Woodstock

Kick off your weekend with the lively, feel-good sound of Lali and the Pops, bringing their warm Catskill-born vibe to Pearl Moon for a vibrant Friday night dinner show.

The band’s roots trace back to the barn of WDST radio personality Jim Rauter, where their unique blend of soulful vocals and upbeat groove first took shape. Fresh off their packed winter residency at Plattekill Mountain, they’re ready to bring that same energy to Woodstock.

Featuring: Lisa Light – songwriter and former member of West Coast rock band The Lovemakers Alexandra Martin (Lali) – lead vocals, radiating charisma and color George Quinn – longtime Woodstocker on bass and vocals Chris Stearns – trumpet, adding rich, expressive brass textures

Expect engaging originals, bright harmonies, and a joyful stage presence that fills the room with life. Settle in for dinner, drinks, and an evening of music that shines with Catskill charm.

✨ Joelle & River – Music • Movement • Medicine Dinner Show Saturday, December 13 · 6:30–8:30pm Pearl Moon, Woodstock

Step into an evening of enchantment as Joelle & River bring their genre-defying, soul-stirring sound to Pearl Moon. Born and raised in Harlem, violinist/vocalist/bassist Joelle and New Orleans–bred multi-instrumentalist and magnetic showman River first crossed paths at NYU — and the chemistry has been sparking ever since.

Blending influences from classical, hip-hop, Caribbean, and Latin traditions, they craft a deeply rooted brew of original music that industry veteran Larry Devivo calls “timeless ear candy.” Their performances feel alive — spirited, transformative, and rich with the sense that music is more than sound… it’s experience, connection, and medicine.

Joelle’s classical finesse, velvety vocals, and radiant presence meet River’s rockstar energy, percussive movement, and multi-instrumental prowess, creating a spellbinding synergy that pulls listeners in and lifts them up. Their mission: to weave music, movement, and healing into one immersive, catalytic journey.

Join us for a night of beauty, rhythm, and soul as Joelle & River light up the room with their powerful, genre-transcending artistry. This is a dinner show you feel as much as you hear. 🌙✨

✨ The Classics – Funky Jazz Christmas Brunch Sunday, December 14 · 11am–2pm Pearl Moon, Woodstock

Slide into the holiday spirit with a festive, feel-good Funky Jazz Christmas Brunch featuring The Classics. This powerhouse group brings groovy rhythms, jazzy sparkle, and warm seasonal vibes — the perfect soundtrack for a cozy December Sunday at Pearl Moon.

Expect soulful takes on holiday favorites, playful improvisations, and plenty of funky cheer to keep your spirits bright. Grab a delicious brunch, settle in, and let the music wrap you up like a holiday hug.

A joyful, jolly, and jazzy way to spend your Sunday. 🎄🎶✨

✨ 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.

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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