The Country’s Oldest Trail-Running Race Is a Grueling Trip Through Beautiful Parks

In 1904, two friends in a San Francisco-based running club came up with an idea so fun and challenging, it would prove popular for decades to come: to race through the wild, wooded landscape of Marin County, California, just north of their city.

At that time, Marin County was only accessible by ferry — the Golden Gate Bridge would not exist for another three decades — although a new train service allowed visitors to travel from the ferry landing in Sausalito north to the Mill Valley region, near what is now Muir Woods National Monument. The area was becoming increasingly popular with tourists looking for a retreat from urban life. One of the running club members owned a cabin near Muir Woods, and some of the men in the club enjoyed hiking in the area on weekends and spending time at the Dipsea Inn, a new business that had just opened on the Pacific Coast.

Distance running was experiencing a boom at that time, inspired by the first modern Olympic Games in 1896 and the first Boston Marathon in 1897. The two friends decided they would run from the Mill Valley train depot out to the inn, which was located on a beach at what is now Golden Gate National Recreation Area. Much of the course would include parts of what is now Mount Tamalpais State Park, in the shadow of the area’s notable peak.

The friends made a bet on who would finish first and set off on a summer day to tackle the steep, strenuous course. The competition was so exciting, the club decided to make it an annual event and named it after the inn that served as the finish line. The following year, club members organized the first official Dipsea Race and expected that a few dozen people might compete; more than 100 men showed up. The tradition has continued nearly every year since.

These days, the race is a bit shorter, eliminating a final trek across the sands of what is now Stinson Beach. The competition is also much larger — capped at 1,500 participants. Women were officially allowed to compete starting in 1971, though they had participated unofficially well before then and had raced in a separate all-female Dipsea from 1918 to 1922. Even with these changes, the overall route is not significantly different from the first challenge 115 years ago.

The trail is not for the faint of heart. Today, the course features three flights of stairs with a total of 700 steps, a series of steep hills and drops, and narrow paths with brambles and poison oak.

Part of what makes the race unusual, however, is the fact that it has never had a strict course. Participants are permitted, with a few restrictions, to take shorter paths through more challenging terrain (with nicknames such as “Suicide” and “the Swoop”) in their attempts to pass other runners.

And passing runners is something that happens regularly in this race due to the other notable factor that makes the event unusual. Most formal races organize participants so that the fastest runners are in the front and the slowest are in the back, attempting to move crowds of people in the most efficient way from start to finish. The Dipsea intentionally reverses this approach, allowing the runners who are typically slowest — boys 6 and under, girls 7 and under, men 74 and older, and women 66 and older — to begin first, while 19- to 30-year-old men, the fastest statistically, start last. The winner is person who finishes first — not the runner with the fastest time.

Organizers intentionally scrutinize past race times based on age and gender with the goal of giving people in every group an equal chance of winning — although no one in the fastest group, known as the “scratch runners,” has won the race in decades. Winners over the past 15 years have included a 72-year-old man, a 64-year-old woman and an 8-year-old girl, however. This twist also explains why there is a whole lot of passing, as each minute for the first 25 minutes of the race a new wave of progressively faster runners is let loose on the course.

“It is like unloading a zoo’s worth of animals in reverse order of mobility and releasing the cheetahs at the end,” New York Times journalist John Branch wrote after finishing 580th in the race last year.

The competition has attracted some well-known contestants over the years, including the late comedian Robin Williams (who ran it in 1984 and said, “Besides the hills, the stairs and the downhill, it wasn’t bad”) and federal prosecutor Robert S. Mueller (who participated while working in the office of the U.S. Attorney in San Francisco in the 1970s). It also has a dedicated following of fans who volunteer and compete year after year. One participant, Jack Kirk, ran 67 consecutive Dipsea Races, his last at the age of 95, earning the nickname the Dipsea Demon.

The 109th Dipsea Race will take place on June 9. Learn more at www.dipsea.org and see a map of where you can run or hike the Dipsea Trail at your own pace on the Muir Woods National Monument website.