History Of The Bermuda Day Cycling Race

[Written by Stephen Wright]

Cycling in Bermuda achieved a landmark moment in 1987 when the island witnessed the first Heritage Day cycling event.

Previously, the race was somewhat of a procession, with cyclists prevented from properly ‘racing’ by the Police and Heritage Day organisers.

That all changed when the authorities finally relented after tireless efforts from cycling enthusiasts, most notably Sinclair Packwood.

In his honour, the race was renamed The Sinclair Packwood Memorial Race following his untimely death in 1999.

Greg Hopkins, who rode to a solo victory that year, told Bernews: “Sinclair was a major influence on getting the event officially recognised as a ‘race’, which is why we decided to name the event after him following his untimely passing.

“He was a true character and highly respected. I was very fortunate to win the first year the event was named after him. It was a very emotional time for everybody.”

The race has grown into the most prestigious event on the local cycling calendar since Buddy Ford outsprinted Packwood to become the first-ever winner in 1987.

A look at the race back in 2004

Packwood also missed out on a maiden title in 1991 when he and Mike Lee collided at the top of Cedar Avenue to hand victory to Carlos De Silva, a two-time winner.

Undeterred, Packwood, who had placed second twice and fourth once, showed the perseverance of a champion by winning back-to-back titles in 1992 and 1993.

Then the race was renowned for pack finishes on Cedar Hill, where the best sprinters would come to the fore and battle for victory.

Jeff Payne, however, signalled a shift in strategy when he shocked everyone in 1997, forming a breakaway with Aaron Schindler at Somerset Bridge and, with the peloton nowhere in sight, pushed on to finish the race a minute ahead of the next group of riders.

Payne became the oldest winner at 59 and the first person to win the cycling race and the Bermuda Half Marathon Derby, in which he triumphed in 1980.

His ploy of attacking early has been emulated by several winners since, notably by MacInnes Looby, a winner in 1995 and 1998, and Hopkins in 1999.

Kris Hedges reigned supreme in the early 2000s, claiming three successive titles in 2000, 2001 and 2002 – a feat yet to be matched.

In 2002, the 13.1-mile route switched to finish in front of the National Stadium on Frog Lane, with Jean-Nicholas Bertrand securing the victory; however, the finish line returned to Cedar Avenue in 2006 when Ricky Sousa Jr grabbed the headlines by crossing the line first.

Wayne Scott claimed the first of three titles in 2008, following up with wins in 2010 and 2014 to equal Hedges’ record of three victories.

A look at the race in 2011

2021 saw a rider surpass the achievements of Hedges and Scott, with Dominique Mayho securing a fourth title, having also triumphed in 2012, 2013 and 2018 – and he also won in 2022 and 2023.

16-year-old Matthew Oliveira joined the list of winners when he stormed to victory in 2016, and a year later, another teenager stole the show, with Kaden Hopkins, then 17, becoming the first son of a champion to win the race. His father, Greg, had triumphed 18 years earlier.

In 2024, Australian Matt Boys claimed his first title with a dominant performance.

Female participants had raced alongside the men until 2007 when Ashley Robinson won the first women’s race.

As of 2022, Nicole Mitchell is most the successful women’s rider, having been crowned champion in 2011, 2018, 2021 and 2022, while Zoenique Williams has a pair of titles after wins in 2014 and 2015.

Alyssa Rowse, then 17, took the title in 2017, Caitlin Conyers won in 2019 and 2024, and Panzy Orlander claimed top honours in 2023.

Mayho, the most dominant men’s rider, said the legacy of Packwood lives on through the race, which he described as “the one everyone on the island wants to win”.

He said: “It’s great the race is named after Sinclair Packwood. He played a vital role in getting us cyclists to compete on Bermuda Day.

“For years, they were fighting to get it, and he was one of those who really helped make it happen.”

Past winners of the Cycling & Sinclair Packwood Memorial Race