The 7.5 mile (12 km) long Dipsea Race has been held annually almost every year since November 19, 1905, starting in Mill Valley, and finishing at Stinson Beach, in Marin County.

In 1904, the Dipsea Inn[4][5] opened on a sandspit north of Willow Camp (later Stinson Beach),[6] built in anticipation of tourists arriving on proposed rail extensions.

Coney and Boas, took up the challenge, setting off on a day in 1904, with bets placed by Club members (Fastest from the train depot at Lyton Square in Mill Valley, to the newly opened Dipsea Inn).

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 Dipsea Trail is the most direct route connecting the town of Mill Valley, located near the northwestern shores of Richardson Bay, with the village of Stinson Beach, situated along the Pacific coast.

Stinson Beach is a popular tourist destination, located about a 30-minute drive north of San Francisco on Highway 1, via the Golden Gate Bridge.

Among the challenges facing participants are the Dipsea Trail's uneven footing, single-track footpaths, and almost invariably steep terrain, featuring about 2,200-foot (671 m) elevation gain and loss over the course.

The uniqueness of the Dipsea Race course owes largely to the opportunity for competitors to choose from any of several alternate routes on diverging and converging trails, adding a competitive premium for strategy, experience, and familiarity with the course.

The Dipsea's handicapping system often produces younger or older winners, which adds to the unusual intrigue and suspense created by the race's permissible shortcuts, like 'Suicide' and 'The Swoop'.

Now organized by the Dolphin South End Running Club, San Francisco icon Walt Stack put together the first Double Dipsea race in 1970.

It is often described as the race where you are "either the hunter or the hunted" where mental toughness is required to overcome not only the 700 steps, the drop into Muir Woods, the Suicide shortcut, and Dynamite and Cardiac hills, but also the handicapped times.