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The 14th Annual Montauk Music Festival
Presented by the Montauk Sun
May 15-18, 2025
Opening Party on Thursday May 15th at the Westlake Fish House
Enjoy an evening of music, appetizers, cocktails, and dancing. Twenty of the Festival Bands will do a sneak preview of their weekend shows- on three stages: inside and out under the tent.
Tickets- $60- includes appetizers and free sponsor drinks along with over four hours of live music.
Over 400 performances beginning Friday afternoon and running through Sunday evening- there will be shows throughout Montauk showcasing 100 acts at about 40 satellite venues.
On Saturday and Sunday- May 17th and 18th
The MAIN STAGES will once again be on the Green in the center of town.
Bring a Beach Chair and/or Blanket- friends and family-and be ready for 2-days of entertainment. No coolers or outside alcohol. Beer/Wine/Soda, and fun at the sponsor tent available during the event.
There will be an admission/donation fee [$20 for 2-day pass], and children under 5 are free- this will allow you entrance for both Saturday and Sunday’s shows 11am- to 5 or 6pm. {Cash or VENMO only}
A percentage of the proceeds will benefit
Lucia’s Angels & East End Coalition for Women’s Cancers
The Montuak Music Festival APP– or Montauk Music Fesival APP for Android with up-to-date schedules, artists, and venue information will be available in May.
2024 promo video- song
2022 promo video- song by Drop the 4

Original Gossip band
Original Gossip band
"Original Gossip is an all original rock band made up of four seasoned musicians from Long Island, New York. Each member has more than 20 years of experience covering all aspects of music including song writing, performing, recording, sound engineering, and teaching. While Original Gossip was formed 4 years ago, the band has over 40 original songs in their repertoire. They found that an audience of all ages has gravitated towards their music through streaming sites, social media, and live performances in popular clubs on Long Island and in the heart of New York City. Original Gossip remains highly dedicated to creating new music. They look forward to bringing their music to the next level and beyond."

Jim Turner
Jim Turner
In over twenty-five years as an acclaimed guitarist, harmonica player, and recording artist, Jim Turner has shared the stage with such greats as B.B. King and Buddy Guy, among many others. He performs both solo and with his band- The Jim Turner Band. He has also appeared in musicals both on and Off-Broadway.

Hope Darling
Hope Darling
Florida-based rockers Hope Darling have been captivating the alternative rock scene with their unique blend of passionate vocals, blissful melodies, and a richly immersive full-band sound that resonates with listeners. For over five years, they’ve been entrancing audiences with music that strikes a perfect balance between raw emotion and polished artistry.With every performance, Hope Darling pulls you into their world, crafting an experience that is both electrifying and deeply moving. Their sound is more than just a listening experience—it's a journey that leaves a lasting impression on the soul of every alt-rock fan.

Gina Cutillo
Gina Cutillo
Billboard artist from Long Island, NY Gina Cutillo has song placements on TV, commercials and film. Her single "Keep On" debuted at #34 on Billboard Top 40 mainstream charts. She has toured with Katy Perry, Paramore, Gym Class Heroes and others on Warped Tour. Besides releasing new music Gina has been also producing rock bands and solo artists.

Calliope
Calliope
Calliope's mission in music is to break all barriers and boxes in which music and their genres carry. She is a Long Island born and raised solo singer/songwriter, recording artist, advocate for mental health & the LGBTQ Community, specializing in all genres from pop/rock, rNb, rock, and pop.

Craig Greenberg
Craig Greenberg
"Craig Greenberg has been hailed as NYC’s most acclaimed post-millennial piano man. Over the past 15+ years, the native New Yorker has been a staple on the city’s music scene, capturing and building on the spirited ivory traditions of greats like Billy Joel, Ben Folds and Randy Newman with sparkling, soulful new musical twists, a larger than life personality and his insightful, dramatic sense of storytelling. Craig has independently released 5 albums (his most recent EP, Between the Sea and the Sky, released in Dec 2022), with new releases slated for 2025. He has performed upwards of 1000 shows, since his start playing in bars while living in Chile, and later Spain, in the early 2000s. His songs have received praise in American Songwriter, the Huffington Post, Relix Magazine, and have been played on radio stations all around the country and internationally (as well as locally on WFUV)."

Diane Gentile
Diane Gentile
Diane Gentile is a New York Singer Songwriter and Producer. Her last album, The Bad and the Beautiful, contributed to large increase in Spotify listeners, YouTube fans, and garnered her tours with ex-Replacements founder Tommy Stinson, and support slots with Alejandro Escovedo, with whom she released a critically acclaimed duet titled "Walk With Me". Her last foray was co-producing the benefit album Silver Patron Saints for artist Jesse Malin, who suffered a rare debilitating spinal stroke. The album contains covers of Jesse's songs from 26 artists, that also culminated in a 2 night sold out benefit show at NY's Beacon Theater, where she performed a duet with Jesse. Diane is currently recording new songs for a fourth full length.

Jay Shepard Band
Jay Shepard Band
Jay Shepard is a multi-faceted guitarist, performer, songwriter, and recording artist. Living on the North Fork via South Carolina, his guitar playing and professionalism are always in high-demand in the studio with Grammy winning producers and on the stage with rock and roll legends. Jay can currently be seen preforming with his band "The JAY SHEPARD BAND" from Montauk to Manhattan, and on the hit Broadway musical “Rock of Ages.” Visit www.JayShepSounds.com to see, hear, and read what all the buzz is about.