Music Events

The Hardwoods – Acoustic Folk Supper Club

Join The Hardwoods for an intimate evening of rich harmonies and rootsy acoustic folk. Their heartfelt songwriting and warm, down-to-earth sound create the perfect backdrop for a cozy supper club experience. Settle in for an inviting night of live music, comfort food, and good company.

THIS IS A FREE SHOW

Call 845-684-5537 to reserve a table for dinner!

Lali and the Pops – Jazz Supper Club

Step into an evening of elegance with Lali and the Pops, serving up smooth jazz standards, soulful vocals, and playful rhythms that set the mood just right. This intimate supper club experience pairs timeless tunes with a curated menu of delicious dishes and craft cocktails. A perfect night out for jazz lovers and foodies alike.

THIS IS A FREE SHOW

Call 845-684-5537 to reserve a table for dinner!

🎶 Live Jazz at Supper Club 🎶 Join us at Pearl Moon for an evening of timeless jazz with the Straight-Ahead Jazz Trio — classic instrumental standards from the '50s and '60s with a smooth mix of blues, soul, and bossa nova.

Featuring: 🎸 Luke Johnson – guitar 🎻 Eric Marshall – bass 🥁 Glenn Hoagland – drums

Reserve your table: 845-684-5537

Eddy Lee Ryder's album 'Sweet Delusions' is a Bold Debut of Heartache, Humor, and Pop Brilliance

Self-described “demented pop” chanteuse Eddy Lee Ryder makes a memorable full-length debut with Sweet Delusions—a sweeping, genre-blurring album that fuses timeless songwriting with dramatic introspection and sly pop sensibilities.

The alter ego of Woodstock, NY-based singer-songwriter Liz Brennan, Ryder blends chanson, country, indie, and classic standards into a fresh strain of modernist pop Americana. Her sharp wit, classic rock spirit, and emotional depth give the album its distinct voice.

Produced by Dave Cerminara (Father John Misty, Weyes Blood) at the Outlier Inn, Sweet Delusions explores apocalyptic romance, bitter regrets, and flickers of hard-won hope. Ryder crafts vivid snapshots of intimacy and loss with charm, humor, and raw vulnerability.

With standout tracks like “Smoke and Mirrors” (featured in cult horror hit Terrifier 2), Ryder proves herself a singular new voice—quirky, honest, and unmistakably real.

THIS IS A TICKETED SHOW

Presale Tickets on Eventbrite.com

($20 tickets are available at the door the day of the show)

Boreal Bossa Nova Jazz Brunch at Pearl Moon

Let the warm, breezy sounds of Brazil transport you at Pearl Moon’s Jazz Brunch with Boreal, led by Brazilian vocalist Mariana Barcellos. Blending classic bossa nova with rich jazz textures, Boreal brings a soulful, relaxed vibe perfect for a Sunday morning.

Expect a graceful mix of vocals, guitar, percussion, bamboo flutes, and cello, creating a lush, melodic atmosphere that pairs beautifully with Pearl Moon’s signature brunch offerings. Whether you're a longtime fan of Brazilian music or simply looking for a refreshing and elegant musical backdrop, this is the brunch to savor.

Reserve your table: 845-684-5537

🎻🌙 Conor Wenk’s Bluegrass Supper Club – Live at Pearl Moon 🌙🎻 Experience an evening of rich, rootsy bluegrass with Conor Wenk, a rare breed of musician—gifted multi-instrumentalist, skilled luthier, and captivating one-man band. Based in Woodstock, NY, Conor crafts and performs with his own handmade stringed instruments, delivering a sonic tour of American music that blends tradition with innovation

Join us at Pearl Moon in Woodstock for the Conor Wenk Bluegrass Supper Club. Enjoy hearty food, cold drinks, and the soulful sounds of Conor Wenk and friends as he bring's traditional bluegrass to life with tight harmonies and skilled picking. It's the perfect way to wind down and soak up some soul-stirring music in a cozy setting.

Free Show! Call 845-684-5537 to reserve a table for dinner!

🎶 Jazz Brunch with Spellbinder Orchestra 🎶

Join us for a captivating Sunday brunch with the Spellbinder Orchestra, an intergenerational, bicoastal collective known for their unique blend of original folk rock infused with elements of classical, world, cabaret, and Eastern European music. Their performances are lively and theatrical, featuring intricate arrangements that transition from rousing and joyful to thoughtful and dreamy. 

Reserve your table for dinner: 845-684-5537

🌈✨ Queer Icons Dance Party w/ DJ TRYST ✨🌈 Get ready to shine at the Queer Icons Dance Party on Friday, June 7 at 9PM at Pearl Moon in Woodstock! DJ TRYST will be serving up a high-energy mix of queer anthems, iconic pop hits, and dancefloor bangers that celebrate the legends who move us—and the vibrant community that keeps the party going. Come dressed in your best and bring your fiercest self!Let’s dance, celebrate, and light up the night! 💃🏽🕺🏽🌙

NO COVER!

🎷🥂 Jazz Brunch with the Tillson Jazz Ensemble – June 8 at Pearl Moon 🥂🎷 Ease into your Sunday with the smooth, sophisticated sounds of the Tillson Jazz Ensemble at Pearl Moon’s Jazz Brunch on June 8. Enjoy a delicious brunch menu paired with timeless jazz classics, cool improvisations, and soulful melodies from one of the Hudson Valley’s most dynamic local jazz groups. The perfect blend of great food and great music in the heart of Woodstock—don’t miss this relaxing and inspired start to your weekend.

Reserve your table: 845-684-5537

🎶 Joelle & River at Supper Club 🎶

Experience the enchanting fusion of classical elegance and soulful rhythms with Joelle & River. Joelle, a Harlem-born violinist, vocalist, and bassist, brings her classical training and velvety voice to the stage. River, hailing from New Orleans, is a multi-instrumentalist, producer, and poet whose dynamic energy and percussive movement captivate audiences. Together, they blend Classical, Hip Hop, Caribbean, and Latin influences to create a timeless, soulful vibe that's not to be missed.

Reserve your table: 845-684-5537

Santa Barbara Supper Club at Pearl Moon

Join us for a high-energy night of music and flavor with Santa Barbara, an electrifying ensemble that blends Latin, funk, and jazz into a vibrant fusion all their own. Performing a dynamic mix of original compositions alongside fresh interpretations of jazz standards, the band delivers a sound that’s both rooted in tradition and refreshingly modern.

Whether you're a jazz aficionado or just in the mood for something bold and rhythmically rich, an evening with the Santa Barbarians promises a musical journey full of groove, soul, and surprises. Pair it with Pearl Moon’s delicious supper offerings for a night that feeds both body and spirit.

Reserve your table: 845-684-5537

🎶 Peter Einhorn – Jazz Supper Club 🎶

Spend your Friday evening with the warm, sophisticated sound of jazz guitarist Peter Einhorn. A celebrated performer, composer, and inventor, Peter has played with legends like Jimmy Cobb and Steve Swallow, and even backed operatic great Plácido Domingo. His unique approach blends technical brilliance with heartfelt expression.

🎸 Jazz, great food, and a touch of magic—don’t miss it!

Reserve your table: 845-684-5537

🎷 Father's Day Jazz Brunch with Jay Collins & Gravy Train 🎷

Celebrate Father's Day with a soulful and grooving brunch featuring Jay Collins & Gravy Train. Led by saxophonist and vocalist Jay Collins—known for his work with legends like Gregg Allman, Levon Helm, and Little Feat—Gravy Train delivers a dynamic blend of jazz, blues, and New Orleans flavor that's sure to delight!

Reserve your table: 845-684-5537 

🎶 Jazz Supper Club with Trinoceros Jazz Trio 🎶

Join us for an intimate evening of classic jazz standards with the Trinoceros Jazz Trio. This ensemble brings a refined cocktail-hour ambiance, featuring piano, upright bass, and drums. With decades of performance experience and deep roots in jazz tradition, Trinoceros offers a sophisticated musical backdrop perfect for a relaxing midweek dinner. 

Reserve your table: 845-684-5537

🎸🌙 Bennett Harris Blues Supper Club – Live at Pearl Moon 🌙🎸 Join us at Pearl Moon in Woodstock for an evening steeped in the rich traditions of American blues with Bennett Harris. A seasoned musician and luthier, Harris delivers authentic Delta blues and ragtime, channeling legends like Robert Johnson and Blind Blake through his masterful fingerpicking and slide guitar techniques. Armed with vintage instruments, including a 1934 National steel guitar, his performances are a heartfelt homage to the roots of blues music.

Savor a delectable supper while immersing yourself in the soulful melodies and rhythms that have shaped the blues genre.It's more than a meal—it's a musical journey through time.

THIS IS A FREE SHOW

Call 845-684-5537 to reserve a table for dinner!

🎷🥞 The Classics Live Brunch – Sunday, June 8 at Pearl Moon 🥞🎷

Join us at Pearl Moon in Woodstock for a delightful Brunch featuring The Classics. This Hudson Valley-based trio brings a dynamic blend of jazz, funk, soul, and reggae to the stage, offering a vibrant musical backdrop to your brunch experience. Known for their versatility, The Classics seamlessly transition between genres, ensuring a lively and engaging performance that complements Pearl Moon's renowned brunch offerings.

Savor a delectable brunch menu while enjoying the rich, soulful sounds of The Classics. It's the perfect way to relax and recharge as you wrap up your weekend.

Call 845-684-5537 to reserve a table for brunch!

The Hardwoods – Acoustic Folk Supper Club

Join The Hardwoods for an intimate evening of rich harmonies and rootsy acoustic folk. Their heartfelt songwriting and warm, down-to-earth sound create the perfect backdrop for a cozy supper club experience. Settle in for an inviting night of live music, comfort food, and good company.

THIS IS A FREE SHOW

Call 845-684-5537 to reserve a table for dinner!

🎶🌙 The Glass Hours Acoustic Supper Club – Live at Pearl Moon 🌙🎶

Immerse yourself in an evening of soulful Americana and country-folk with The Glass Hours, the captivating duo of Megan Barbera and Brad Armstrong. Blending Megan's Colorado mountain roots with Brad's Southern heritage, their music weaves rich harmonies and evocative storytelling into a tapestry of acoustic sound. Their self-titled debut album, released in March 2024, garnered acclaim from outlets like Americana UK and The Bluegrass Situation, leading to performances at notable events such as NYC’s Underwater Sunshine Festival. Currently based in New York's Hudson Valley, The Glass Hours continue to enchant audiences with their intimate performances and authentic songwriting.

Join us at Pearl Moon in Woodstock for an evening where heartfelt melodies meet a cozy dining experience. Savor delicious cuisine while being serenaded by the harmonious blend of voices that define The Glass Hours.

Call 845-684-5537 to reserve a table for dinner!

🎶 Jazz Supper Club with Trinoceros Jazz Trio 🎶

Join us for an intimate evening of classic jazz standards with the Trinoceros Jazz Trio. This ensemble brings a refined cocktail-hour ambiance, featuring piano, upright bass, and drums. With decades of performance experience and deep roots in jazz tradition, Trinoceros offers a sophisticated musical backdrop perfect for a relaxing weekend dinner. 

THIS IS A FREE SHOW

Call 845-684-5537 to reserve a table for dinner!

Jay Collins' Gravy Train – Sunday Jazz Brunch at Pearl Moon

Spend your Sunday morning with the soulful sounds of Jay Collins' Gravy Train at Pearl Moon’s Jazz Brunch in Woodstock. Led by acclaimed saxophonist and vocalist Jay Collins—known for his work with Gregg Allman, Levon Helm, and Little Feat—the band brings a smooth, groove-filled blend of jazz, blues, and New Orleans flavor that’s perfect for a relaxed brunch setting.

Gravy Train features a stellar rhythm section, including Matt Finck on guitar, Adam Coté on bass, and Lavon “Lee” Collins on drums. Together, they deliver a rich, dynamic sound that pairs beautifully with Pearl Moon’s fresh and flavorful brunch menu.

Come for the music, stay for the vibe. It’s a Sunday tradition!

Reserve your table: 845-684-5537