National Register of Historic Places in Marin County
The Dipsea Trail has been used by recreational hikers since the 1890s.
The trail traverses 7.44 miles between Mill Valley and Stinson Beach. Altitudes range from sea level to 1,360 feet. Most of the trail is on public land, including Mount Tamalpais State Park, Muir Woods National Monument, and the Golden Gate National Recreation Area. Many segments have names that sound like ski runs: Dipsea Steps, Suicide, Dynamite, Cardiac, The Swoop, Insult, and The Moors.
The trail is the location of the annual Dipsea Race, the oldest cross-country trail race in the United States.
The race began in 1904 as a friendly competition between Charles Boas and Alfons Coney, two members of the Olympic Club, which is the oldest athletic club in the United States, founded in San Francisco in 1860.
Boas and Coney, while hiking Mt. Tamalpais, came upon the Dipsea Inn, a newly built hostelry by the Bolinas Lagoon. They challenged each other to a foot race from the Mill Valley depot to the inn. The course followed an established series of trails. After the race, Boas and Coney and other members of the Olympic Club formed the "The Dipsea Indians." Adopting Indian mascots in sports was common at the time. Indians were considered athletic and close to nature without the burdens of civilization.
The Dipsea Indians decided to establish an annual race along the route Boas and Coney had run. The first race, held on 19 November 1905, was expected to attract a few dozen runners. It drew over one hundred.
The first race set as tradition two distinctive aspects of the Dipsea Race: a handicapping system and an open course.
Handicaps, or measured head starts, date back to the original Greek Olympic Games. Handicaps allow runners of all capabilities an opportunity to win. One winner was seventy years old. One winner was nine years old. Jack Kirk, the Dipsea Demon, finished seventy-three consecutive races and ran his last race at the age of 97.
The open course allows runners to choose any route they please as long as they start and finish in the right places. For the most part, runners followed the established route. More recently, runners have been restricted in sensitive areas to specific trails to avoid environmental damage. Some portions of the original trail are only open on race day.