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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

Annalyse & Ryan
Annalyse & Ryan
Annalyse & Ryan are a NY-based Americana duo. Their sound and songs take listeners on a soulful, rootsy journey, “resounding from the hollers with a haunting beauty” (Jeff Biggers, Huffington Post). The sweetness and severity in their music echos a cross between The Civil Wars and Tedeschi Trucks Band. Annalyse & Ryan’s strong harmonies melt together seamlessly, with an undeniable edge: a symbiotic clash reminiscent of their differing senses of place, yet their ironically parallel styles of seeing the world. Their music has been featured on CBS, BBC, and in multiple documentaries. The duo is touring this spring in support of their new EP Trilogy. The album features a phenomenal group of musicians brought together for this 3-song project.

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.

Drop the 4
Drop the 4
The retro-future post funk fusion phenomenon. Complete with horns, vocals, and a rhythm section that will keep you dancing the entire time.

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.

Charlize Tuozzo
Charlize Tuozzo
"Charlize was born on 11-11-11 in Long Island NY. She is a 11-year-old actor, singer songwriter. Charlize was a finalist at the famous Amateur Night at The Apollo NYC, where she received a standing ovation for her rendition of Sara Bareilles “She Used to be Mine”. Most recently she opened for Tommy DeCarlo lead singer of Boston at Tanner Park NY. Charlize will be releasing her first original single in March of 2023 At just 10 years old, Charlize is the organizer of the sold out “Charlize Tuozzo’s Ukraine Relief Concert”, featuring several professional singers, including special guests Sal Valentinetti golden buzz winner from Americas Got Talent and former Miss Connecticut Olga Litvinenko. The concert took place at the famed Paramount NY, raising over $2900, which was donated to Bethenny Frankel’s BSTRONG Ukraine Relief. "

Nora Conlon
Nora Conlon
Nora Conlon just finished her Junior year at the Clive Davis Institute of Recorded Music at NYU. Growing up in Springs, she has been playing solo gigs around the East end of Long Island for years now. At school Nora has been working on her craft as a songwriter and audio engineer and during her Fall semester abroad, she dropped her first single “Cut it Out” on all streaming platforms. Nora’s sound is inspired by artists, Mitski, Jeff Buckley, Hozier, and Madison Cunningham and she is excited to play some new songs at the Montauk Music Festival this year.

Melody Rose
Melody Rose
"Melody Rose attributes her unique vocal and songwriting style to her various musical upbringings. The daughter of a singer and a music industry executive, she spent her childhood in the studio, or backstage at Madison Square Garden, observing the inner workings of the world of Rock & Roll. Her operatic training and vocal jazz training surpass a decade. Upon receiving her M.A. in music composition, Melody continued to work on her craft as a singer-songwriter, and subsequently released her debut, self-titled album in 2015. Melody’s live performances have taken her to Europe and to various music conferences and festivals along the east coast. She is currently performing as a member of the Manhattan Band for Norwegian Cruise Lines. Music Magazine UK raves, “Soul is definitely one thing that Melody has no shortage of, and you’ll be sure to listen again and again to gain an insight in to this young up-and-coming artist.” Stay tuned as Melody Rose plans the release of her sophomore album, ‘Inside the Skies.’ "

Chelsea Takami
Chelsea Takami
Chelsea Takami (acoustic guitar & vocals) is a soulful, charismatic, and dynamic singer-songwriter from Long Island, NY. She recently opened up for Pat Benatar at The Paramount in Huntington, where she also performs every Sunday at their art gallery/bar called Spotlight. Takami performs full-time on Long Island. She's known for her dynamic range of both cover and original songs, and is always on-point with her fun, energetic performances.