We are committed to providing our local athletes with the best cycling events and opportunities.
Race Calendar 2026
Fit Check #1
TT Series
April 26
May Classics
4 race series
May 10 - 24
National Championships
ITT & Road Race
June 20 & 21
Cayman Cup
Road Race
October 18
Pirates Week Crit & Kiddies Dash
Crit Race
November 9
National Championships
Open to all athletes in the Cayman Islands, the Championships offer a stage that brings together the best riders in the Cayman Islands, all competing for the highest cycling honour.
May Classics
A 4-race, categorised cycling series encompassing circuit, road and time trial races across the island
Cayman Cup
Cayman premier cycling event crown the best cyclist on Cayman’s roads in an all-out road race experience!
FitCheck Series
4 time-trial style races per year, hosted each quarter by Cayman Cycling, with the results acting as your “fit check” to see how much you are improving.
Pirates Week Criterium
A high adrendaline Criterium race around the nation's capital
