The race gained a degree of notability in 2005 when Matha Stewart announced her intention to participate. While her pastel-coloured pumpkin did appear in the race, Ms Stewart could not participate as permission to enter Canada was delayed after her release from incarceration in the ImClone affair; when permission was finally granted, weather prevented her from reaching Nova Scotia on time. Various other celebrity participants have raced, notably local member of parliament Scott Brison, who has appeared in several of the races.
Windsor was not the first to feature a giant pumpkin as a water-borne craft. That distinction falls to Wayne Hackney of Winchester , New Hampshire who paddled in a pumpkin he grew in 1996. However, the regatta has inspired several other pumpkin regattas, including one at the University of Wisconsia -Madison and on Lake Champlain .