The John T. Memorial Cycling Race was founded in 1999 by avid cyclists with the Hon. Evan Gumbs and Carl Avery Thomas (both past presidents of the cycling association) being the main founders. The race which is held annually in July is hosted in memory of the late John Thomas who was affectionately known to all as John T.

John T. was a lover of cycling and was very instrumental in the development of the sport in Anguilla. Many cyclists from that era still tell the story of how John T took them overseas to compete and did so with his personal funds. This gave the cyclists exposure and raised interest in the sport and created bond between Anguilla and many of the islands in the region, especially with islands such as Antigua and St. Maarten. Bonds which still stand to this day.

John T. died in 1991 and to carry on his legacy the John T. Memorial Race was created and has grown tremendously.  The John T. Memorial Cycling Race is now one of the Caribbean's largest and most anticipated cycling competitions. Cyclists from various Caribbean Islands travel to Anguilla each year to compete in this prestigious race .