Combining violin, guitar, percussion, and vocals, multi-instrumentalist Chris Tedesco weaves together unique versions of popular songs in a variety of genres. From Coldplay and Sting to Taylor Swift and Usher, Chris uses live looping to create a layered musical soundscape that sets the right mood and vibe.

June 7th

Hamptons native, Alessandro Giangola is a singer/songwriter who has been playing music since he was young. Though his versatile style ranges from pop, to indie, to rock, he always aims to uplifting the crowd with positivity. He’s released several singles and loves playing original music at his shows. Bring friends and family and us for a night of unique and upbeat vocals.

June 14th

Jay Shepard is a multi-faceted guitarist, performer, songwriter, and recording artist. Living in New York City, his guitar playing and professionalism are always in high-demand in the studio and on the stage. Most notably renown for his written works sung by Aerosmith "Livin' On The Edge” 

June 21st

Get ready for an unforgettable night as Audawind takes the stage. This three-piece band brings a bold fusion of country rock, pop, and hip hop that will have you dancing ‘til the last chord. Join us in the Tavern for great music, craft cocktails, and Shelter Island vibes.

June 28th

Jay Shepard is a multi-faceted guitarist, performer, songwriter, and recording artist. Living in New York City, his guitar playing and professionalism are always in high-demand in the studio and on the stage. In addition to being an “A-level” sideman, Shepard’s own music has been described as having commercial appeal while possessing an endearing personal quality with an eclectic feel.

July 5th

Combining violin, guitar, percussion, and vocals, multi-instrumentalist Chris Tedesco weaves together unique versions of popular songs in a variety of genres. From Coldplay and Sting to Taylor Swift and Usher, Chris uses live looping to create a layered musical soundscape that sets the right mood and vibe.

July 19th

Deanna Hudson is a Long Island based singer/songwriter with a moody pop/rock vibe. She specializes in Classic Rock, Top 40, Pop & Punk. Teaching herself to sing and play guitar at 25 years old, she's commanded the stage across Long Island, expanding from Long Beach to Montauk, Queens to Greenport.

July 26th

Don’t miss the incredible Julia King as she brings her soulful voice and magnetic stage presence to The Chequit Hotel. Experience an evening of powerful vocals and captivating melodies in an intimate, seaside setting.

August 9th

Get ready for an unforgettable night as Audawind takes the stage. This three-piece band brings a bold fusion of country rock, pop, and hip hop that will have you dancing ‘til the last chord. Join us in the Tavern for great music, craft cocktails, and Shelter Island vibes.

August 16th

Combining violin, guitar, percussion, and vocals, multi-instrumentalist Chris Tedesco weaves together unique versions of popular songs in a variety of genres. From Coldplay and Sting to Taylor Swift and Usher, Chris uses live looping to create a layered musical soundscape that sets the right mood and vibe.

August 23rd