Skip to main content

May Classics

West Bay Circuit

10 May 2026 | 7:00am

South Sound Time Trial

17 May 2026 | 6:30am

East End Road Race

18 May 2026 | 7:00am

CostULess Circuit

24 May 2026 | 7:00am

Courses Info

Categories

Juniors
Cat 1-4
Women
Masters
Super Masters

Entry Fee

Series | CI$100.00
Single Race | CI$30.00

Registration

Online ONLY

Race Partners

An array of cycling prowess is needed to conquer the 4 races – the technical West Bay Circuit, the Queens Highway individual time trial, the grueling East End Road Race and the speed of the CostULess Circuit.

Open to ALL Cayman-resident athletes, category winners will be crowned in Category 1-4, Masters (40-49), Senior Masters (50+), Elite Women and Juniors (under 18). Overall winners with pull on the Red Jersey as the May Classics champions!

Full Series

CI$100/series

Single Race

CI$30/race

The Green Jersey rewards the rider who is leading the points classification at the end of the Classics. Sprint points will be allocated across the series and the riders with the most total sprint points in each category after race 4 will be crowned the Sprint Champion!

West Bay Circuit (Race 1)

The opening race of the weekend, the West Bay Circuit, is the most technical of the races, combining the speed of the straights on the Bypass, with criterium-style corners through West Bay.

Distance

24.8 miles

All categories

Laps

8

3.1 miles/lap

Category Points

1st - 5th

10-8-6-4-2pts

Sprint Points

Laps 2, 4, 6 & 8

3-2-1 pts

Course

Flat, Technical

South Sound Time Trial (Race 2)

The 2nd event, the South Sound ITT will cover 9.6 miles – the same for all categories – with athletes setting off at pre-determined intervals.

Distance

9.6 miles

All categories

Laps

1

4.8 miles out/back

Category Points

1st - 5th

10-8-6-4-2pts

Course

Flat, Fast

East End Road Race (Race 3)

The East End Road Race will feature a mass start for the athletes, with staggered starts & distances of the East End Circuit course for the various categories.

Distance

18.7 miles

Juniors

Distance

37.4 miles

Women, Category 4, Masters, Super Masters

Distance

56.1 miles

Category 1 - 3

Category Points

1st - 5th

10-8-6-4-2pts

Sprint Points

Laps 1 & 2

3-2-1pts

Course

Most Flat, some inclines, high temps

CostULess Criterium (Race 4)

The CostULess Criterium course will close out the series with what has traditionally been a fan-favorite – a fast, exciting race on a quick looped course.

Distance

45 mins + 3 laps

All categories

Laps

18-21 (estimate)

1.2 miles

Category Points

1st - 5th

10-8-6-4-2pts

Sprint Points

Laps 3, 6 & Final

3-2-1 pts

Course

Flat, Fast, Roundabouts

  • Registration for the event will be online only via the form below.
  • Your racing age is your age on the 31 December of the current year
  • NO race day registration will be available.
Name
Membership/License
If you need to sign up for membership visit https://www.caymancycling.org/membership/
Registration Type
Submissions less than 24 hours before each race commencement will not be processed.
Racing Experience

Agreement
1. I ACKNOWLEDGE THAT Cycling is a potentially hazardous activity and carries with it the risk of injury or death. I, the undersigned, hereby assume the risk of participating in the cycling event.
2. I CERTIFY that I am physically fit and have not been advised against participating by a qualified health professional.
3. IN CONSIDERATION of the following and of your accepting this entry, I hereby agree on behalf of myself, my executors, administrators, heirs, next of kin, successors, assigns, and any other person who may claim or sue on my behalf, the following:
4. Agree to abide by the Cayman Islands Road Rules and Regulations. (Roads remain open to Traffic) Abide by the Instructions provided by the event Organizers, Marshals, and volunteers
5. To WAIVE, RELEASE and FOREVER DISCHARGE from any and all claims, losses, economic or otherwise, or liabilities for death, personal injury, partial or permanent disability, damage to property, all payment relating to medical costs or costs of hospitalization, theft or damages of any kind, which may arise as a result of or relate to my participation in the said Cycling event the following persons or entities: CAYMAN ISLANDS CYCLING ASSOCIATION, THEIR DIRECTORS, MEMBERS, AGENTS AND OFFICERS, EVENT SPONSORS AND VOLUNTEERS, EVEN WHERE SUCH CLAIMS, LOSSES OR LIABILITIES ARE CAUSED AS A RESULT OF THE NEGLIGENT ACTS OR OMISSIONS OF THE PERSONS OR ENTITIES I AM HEREBY RELEASING OR ARE CAUSED BY THE NEGLIGENT ACTS OR OMISSIONS OF ANY OTHER PERSONS OR ENTITIES;.
6. To confirm that I am SIXTEEN years (16) of age or older, that I have read the Waiver and I understand its contents and agree and accept to be bound by the terms and conditions contained within the Waiver.
7. To assume the risk of cycling on roads/land that may not be fit for purpose, including but not limited to falls, contact with other participants, effects of weather including but not limited to heat and/or humidity, defective equipment, road condition, water hazards, any hazards that may be posed by spectators or volunteers, all risks being known and
8. To further acknowledge that these risks include risks that may be the result of the negligence of the persons or entities mentioned above for any of the claims, losses, liabilities that I have waived, released or discharged herein;
9. To agree not to sue any of the persons or entities mentioned above for any of the claims, losses, liabilities that I have hereby waived, released or discharged herein;
10. To indemnify and hold harmless the persons and/or entities mentioned above from any and all expenses incurred, claims made, or liabilities assessed against them including but not limited to attorney’s fees and litigation expenses arising out of or resulting directly or indirectly, in whole or in part, from (i) my actions or inactions (ii) my breach or failure to abide by any part of this Waiver Including but not limited to my covenant not to sue (iii) any breach on my part in abiding by any rules provided by the organizers or (iv) any other harm caused by me;
11. Submission of properly completed registration form, presentation of required documentation, payment of chip rental fee and acceptance of race number is acknowledgement of the acceptance of full responsibility for his/her participation in the event.