On a rainy November 19, 1905, the first Dipsea Race was held, on a 7.4-mile course, with 110 runners, by members of the San Francisco Olympic Club, from the Mill Valley train depot to the then-new Dipsea Inn, on a sand spit now called Seadrift, in the Bolinas Lagoon between Stinson Beach and Bolinas, taking place annually, only being cancelled a few times in its history: 1932-1933 due to the race not being able to earn enough funds to be financially viable due to the Great Depression, 1942-1945 due to World War II, and 2020 due to the COVID-19 pandemic. In 1977, the race was almost cancelled as the previous year saw an overwhelming number of participants due to the running boom of the 1970s - the local government was worried about overcrowding and also did not want to close down nearby streets. The Marin County Board of Supervisors voted 3-2 to cancel the race until changes could be made. The race ended up being delayed and held in October instead.