In the first years, the Festival was held in November and October, dates chosen to fulfill the objective of increasing visitor arrivals to the island during the soft tourist season. In 1999 there was no Festival as this proved to be a decision year as to the future of the Festival. Rain had haunted the event year after year, resulting in either cancellation or shortening of performances, and this combined with the worry about decreasing sponsorship for the event, created grave concerns for the organizers. Hence, after serious consideration the decision was made to postpone the Festival.
In 2001, the Festival was lured back to Montego Bay by a group of hoteliers and the move was made to what was soon to become the favorite venue for the event, Cinnamon Hill golf course. For five years, many unforgettable experiences were created under the magical Jamaican skies on these precisely manicured lawns surrounded by hillside bonfires. Patrons were thrilled with the performances of Kenny Rogers, Air Supply, Dionne Warwick, Alicia Keys, John Legend, Nora Jones, Bo Diddley, Monty Alexander, Third World, Shaggy, Pattie Labelle, Al Green and others. They sang and the people came, and under the guidance of Walter Elmore, the current owner of the event who took over the reins in 2004, it became Jamaica’s largest Festival, bringing thousands of visitors to the islands and thousands of Jamaicans to Montego Bay.
As the reviews about the Festival got out both locally and internationally, the attendance grew to over 35,000, forcing yet another move and in 2006 the Aqueduct at Rose Hall became the new home. At this venue patrons were treated to legends such as Earth Wind and Fire, Diana Ross, Chicago, Lionel Richie, Anita Baker, Spyro Gyra, Randy Crawford, Koko Taylor, plus new entrants such as Nikki Yanofsky, Matisyahu, Estelle. The new home of the festival once RELAUNCHED drew in Hall and Oates, Joss Stone, Machel Montano HD, Jon Secada, Babyface combined with crowd favorites Gladys Knight, Monty Alexander, Third World and Billy Ocean.
For its 15th Anniversary, the Festival welcomed Maroon 5, Natalie Cole, Diana King, Tavares, SWV, Regina Belle, Alison Hinds, Laura Izibor, Taurus Riley and Committed, winner of NBC’s Reality show The Sing Off, to its stage.
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