Gershwin Lake
Gershwin, named after the famous composer George Gershwin, has always had an insatiable appetite for music. This was manifested early in his childhood. When kids were running around playing marbles, he found himself trying to build band stands out of old biscuit tins and nylon. One day, Gershwin so happened to be in the presence of Anguilla's legend Bankie Banx. The image and swag of this musician never left his mind. He started to emulate this rock star character by placing an unused mop on his head to imitate dreadlocs while playing his tin guitar.
Today, Gershwin now follows the teachings of Rastafari and has etched his way into the music scene. He has performed throughout the Caribbean and Canada and has produced two albums along with several singles. He is an avid songwriter and producer who continues to pursue his musical dreams. He is not after fame or fortune but believes that he is Jah's messenger and is here to do Jah's work.
Tyree Peters
Tyree Peters is a vocalist and performing artist with a passion for music and live entertainment. With over five years of experience performing within the tourism industry, he has developed a dynamic stage presence and an ability to connect with diverse audiences through engaging, memorable performances.
His musical journey has been shaped by his dedication to vocal performance and music education, earning him third place regionally in the CSEC Music examinations. He has continued to refine his artistry through live performances and his involvement with Anguilla’s entertainment scene as the male lead vocalist of Mystic Vybz Band.
Beyond music, Tyree works as a Sales and Marketing Assistant at Cap Juluca, where he combines creativity and storytelling to personalise guest experiences. Whether performing on stage or creating meaningful experiences through his work, he is driven by a passion for connecting with people and using creativity to inspire, entertain, and bring audiences together.
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Andy Mathew
Andy Mathew’s musical career spans over thirty-five years, beginning when he was featured in school programmes at age eight. In 1995, a demo project for BET Television owner Bob Johnson on Anguilla helped define his unique musical direction.
Merging R&B, soul, and reggae, Andy innovated “regg-oul”—a genre blending soul's passion with reggae's playful rhythms. His discography includes albums such as The Score (2015), My Redemption (2025), and Glory (2026). A versatile performer, Andy spent years entertaining international audiences in Europe under Valtur, earning a Bachelor Degree in Music Practice and Technology from the University of London in 2010. Fluent in Italian and Spanish, he is currently penning his next album.
Who's Performing!?
Tina Rogers
Tina’s musical journey began at the age of 12, sparked by singing in church and discovering a deep, enduring passion for music. Over the years, singing evolved from a cherished hobby into a defining part of her identity. Known for her rich and powerful alto voice, she has recently lent her talent to the Anguilla National Choir. Now at 31, Tina continues to grow, learn, and share her extraordinary gift with the world through the power of music.
Disruptors Steel Orchestra
Disruptors Steel Orchestra is a dynamic, youth-driven musical ensemble dedicated to celebrating the rich traditions of steelpan music while pushing the boundaries of creativity and performance. Founded and directed by Casey Richardson, the orchestra evolved from Fusion Beat Steel Orchestra, established in 2025, and comprises talented young musicians united by their passion for music, culture, and artistic excellence.
The ensemble has made its mark through vibrant performances at major cultural and national events, including the Anguilla Summer Festival’s Grand Parade of Troupes, showcasing the energy, versatility, and talent of Anguilla’s next generation of musicians.
Disruptors Steel Orchestra is committed to youth empowerment, musical development, cultural preservation, and redefining the steelpan experience locally.
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Roxanne “Queen Roxxy” Webster is one of Anguilla’s most celebrated and decorated calypsonians, with over two decades of experience and an impressive collection of 21 major crowns across the Caribbean. Beginning her musical journey at just ten years old as “Lil’ Roxxy,” she has evolved into a powerhouse performer, renowned for her commanding stage presence, lyrical prowess and versatility across calypso and soca.
Over the past decade, she has dominated the Anguilla Senior Calypso Monarch competition, capturing the coveted title seven times. Her remarkable achievements also include two Leeward Islands Calypso Monarch titles, three Groovy Soca Monarch crowns and one Power Soca Monarch title. In 2019, she made history by simultaneously holding three prestigious titles: Groovy Soca Monarch, Senior Calypso Monarch, and Leeward Islands Calypso Monarch.
Queen Roxxy continues to champion Caribbean music and heritage, cementing her legacy as one of Anguilla and the region’s most accomplished female calypsonians.
Queen Roxxy
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Hailing from the vibrant island of Saint Lucia, Teddyson John is a captivating vocalist, songwriter, and cultural ambassador whose sound transcends genres and borders.
Blending the soul of the Caribbean with infectious rhythms, rich melodies, and an electrifying stage presence, he creates a musical journey where Soca, Reggae, Soul, and World Music collide.
An internationally recognized performer, Teddyson brings something rare to the global stage: the heartbeat of the Caribbean, delivered with the soul of a storyteller and the energy of a showman.
From intimate musical experiences to explosive festival stages, his performances are more than concerts—they are celebrations of life, culture, and human connection.
One voice. Many rhythms. A world of possibilities.
Teddyson John
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