Music Events

Join us for a special dinner and folk music experience with Rhode Island–based collective Undercover Cameo, as they celebrate the release of their new single “Hands” with a string of intimate performances throughout the Northeast.

Featuring Lucas Neil, Olivia Charlotte, Sandy Allen, and Elizabeth Beisel, this multi-generational group creates an atmosphere of love and healing through ambient arrangements and poetic songwriting. It's more than a show—it's a soul-nourishing evening of connection, comfort food, and beautiful sound.

📍 Pearl Moon, Woodstock

📞 Reserve your table: (845) 684-5537

Join us for an Indie Folk Dinner Show with Max Bartos, a rising 22-year-old singer-songwriter from Lancaster, PA, now making waves in NYC. With a sound often described as “Mumford & Sons meets Green Day,” Max fuses raw punk spirit with soulful folk storytelling. Known for originating the role of Darren in Broadway’s Sing Street, he’s released several projects including the 2023 album Memento Mori. His upcoming EP Waiting at the Crossroads arrives August 2025.

📍 Pearl Moon, Woodstock 🍷 Great food. Soulful jazz. Cozy vibes.

📞 Reserve your table: (845) 684-5537

Ease into your Sunday with the smooth, soulful sounds of the Tillson Jazz Ensemble. This talented local group brings a sophisticated blend of classic jazz, swing, and modern grooves—perfectly paired with Pearl Moon’s beloved brunch offerings.

Whether you're sipping a mimosa or savoring locally sourced favorites, the Tillson Jazz Ensemble sets the mood for a laid-back, elegant afternoon in the heart of Woodstock.

Reservations recommended for best seating.

📍 Pearl Moon, Woodstock 🍷 Great food. Soulful music. Cozy vibes.

📞 Reserve your table: (845) 684-5537

Drawing deep inspiration from the rich musical heritage of New Orleans, Joelle & River craft an intoxicating blend of smooth vocals, dynamic percussion, and heartfelt melodies. Their sound captures the spirit of the Crescent City — lively, soulful, and deeply rooted in jazz tradition while embracing modern grooves.

Joelle’s velvety voice flows effortlessly over River’s rhythmic percussion and movement, creating a mesmerizing experience that transports you straight to the heart of the French Quarter. Their performances are a celebration of culture, music, and storytelling — a perfect pairing for an evening of delicious locally sourced dining and live jazz.

Enjoy a full dinner & drink menu during the show.

📍 Pearl Moon, Woodstock 🍷 Great food. Soulful music. Cozy vibes.

📞 Reserve your table: (845) 684-5537

Experience a genre-bending night of music with Perry Foster, a Hudson Valley-based singer-songwriter and multi-instrumentalist originally from Arizona. Known for blending folk, jazz, rock, and klezmer into a style all his own, Perry brings a deeply creative spirit to every performance—ranging from pub sing-alongs to immersive art installations.

Perry’s work has earned acclaim from the Arizona Commission on the Arts, Phoenix Art Museum, and beyond—don’t miss this uniquely expressive evening. Featuring Jamie Mohamdein on stand up bass!

Enjoy a full dinner & drink menu during the show.

📍 Pearl Moon, Woodstock 🍷 Great food. Soulful music. Cozy vibes.

📞 Reserve your table: (845) 684-5537

Join us for a soul-stirring night of rootsy rhythm and blues with Bennett Harris, a seasoned bluesman known for his smoky vocals, fingerstyle guitar, and heartfelt storytelling. Drawing from Delta blues, ragtime, and early American folk traditions, Bennett brings an authentic sound that’s both timeless and electrifying.

Whether he’s sliding on a resonator or crooning a classic, Bennett delivers a performance that feels like a front-porch jam with a whole lot of soul.

Enjoy full dinner and drink service throughout the show.

📍 Pearl Moon, Woodstock 🍷 Great food. Soulful music. Cozy vibes.

📞 Reserve your table: (845) 684-5537

Transport yourself to the sun‑soaked streets of Rio with the Stephen Johnson Nu Bossa Band, blending classic bossa nova with global rhythms and contemporary groove. Fronted by UK‑born and Berklee‑trained guitarist Stephen Johnson, this trio brings a refreshing twist on the genre—melding jazz, samba, and socially conscious vibes

Beyond his sleight-of-hand guitar and velvety vocals, Stephen is also known as a dedicated artivist, using music with Future350 Nu Bossa to champion social and environmental justice 

Joining Stephen onstage are Michael Colletti on upright bass and Pablo Shine on congas, crafting an intimate yet dynamic sonic landscape that dances between languid bossa rhythms and vibrant percussion. Expect smooth vocals, deep groove, and a meal paired perfectly with each rhythmic twist.

Enjoy full dinner and signature cocktails while the music flows.

Spend your Sunday soaking in the smooth, sophisticated sounds of Peter Einhorn, an acclaimed jazz guitarist and composer whose expressive playing has graced stages around the world. Known for his lyrical touch, inventive improvisation, and collaborations with jazz legends, Peter brings both warmth and virtuosity to every performance.

Enjoy a laid-back afternoon of world-class jazz paired with Pearl Moon’s beloved brunch menu—featuring locally sourced dishes, cocktails, and good vibes all around.

Reservations recommended for best seating.

Join us for an intimate evening of music with RALLO, the musical moniker of acclaimed film director and producer Alyssa Rallo Bennett. With deep roots in storytelling, RALLO blends soulful vocals and evocative songwriting shaped by her early years playing multiple instruments and fronting a rock band.

The daughter of a poet and a theatrical mother, her creative path evolved into filmmaking—where her award-winning films have screened at festivals like Tribeca, Woodstock, Newport Beach, Toronto Independent, and Seattle International Women’s Film Festival.

Now, RALLO returns to her musical roots, inviting you into a world where melody meets meaning.

✨ Dinner & Music in the Heart of Woodstock 📍 Pearl Moon

Enjoy a night of delicious food and genre-bending music with SoulCake—where blues, garage rock, pop, and moody ballads collide in unexpected ways.

Led by NYC singer-songwriter Joff Wilson (The Bowery Boys, Irthlings, Fugitives), who’s shared stages with blues legends like Junior Wells and Joe Beard, the band features Laura Sativa on flute and percussion and Sarafe on bass and vocals. Whether an acoustic trio or full electric set, SoulCake brings surprises, spontaneity, and serious groove.

🍽️ Dinner & a Show 📍 Pearl Moon, Woodstock

Join us for an evening of smooth grooves and soulful energy with Lali and the Pops. Fronted by the captivating vocalist Lali, the band blends jazz, soul, and R&B into a rich, uplifting sound that’s both timeless and fresh.

Known for dynamic arrangements and feel-good vibes, Lali and the Pops bring a playful, heartfelt energy to every performance—perfect for a night of great music and great food in the heart of Woodstock.

🍷 Jazz Dinner Show 📍 Pearl Moon, Woodstock