First held in 1987, the Sinclair Packwood Memorial Race is a longstanding part of Bermuda Day and one of the island’s most prestigious cycling events. It has taken place annually, with the exception of 2020, when the COVID-19 pandemic forced its cancellation.

Originally known as the Bermuda Day Cycling Race, it was renamed in 1999 in honour of Sinclair Packwood, a respected Bermudian cyclist whose efforts helped establish the official race. Packwood was himself a two-time winner, taking consecutive victories in 1992 and 1993.

 
The event is sanctioned by the Bermuda Bicycle Association but developed as a part of the activities held on Bermuda Day.  Planning meetings for the day include representatives of the half marathon derby, junior classic and the department of culture (responsible for the parade).  These meetings are run by Bermuda Police Service and include St. John’s Ambulance, Bermuda Regiment, BPS, Corporation of Hamilton and several other agencies.