If you’re an outdoors enthusiast who’s lived in the Bay Area for any amount of time, you’ve more than likely heard about the Dipsea Race. The approximately 7.4-mile trail race is one of the most competitive and quirky in the local running scene, and its history is unparalleled: First held in 1905, it’s the oldest trail race in the country and the second-oldest footrace in the country, second only to the Boston Marathon.
It was started on a bet in 1904 among a group of hardy young men from San Francisco's Olympic Club, who wondered what was the quickest route from Mill Valley to Stinson Beach. The winner would be the first one who got there, no matter what the route; the tradition has evolved into one of the most well-known races of the trail running community.
But make no mistake, this is no ordinary run through the woods. Like the Bay Area itself, the Dipsea is a one-of-a-kind race that makes up its own rules, starting with its old-school registration process. It’s done entirely via snail mail—no online registration—largely to give locals an advantage (and bribing for one of the coveted 1,500 spots also is encouraged). Then, there’s the course: a brutal, up-and-down grinder that’s infamous for both its elevation gain (nearly 2,000 feet) and terrifying terrain (singletrack, steps, footbridges, and steep, gravelly sections with names like Suicide, Insult, and Cardiac).
Finally, the Dipsea is unique in the fact that it has a handicapping system based on age. The oldest and youngest runners start first, with each age/gender wave following each minute after. Male runners between 19-29 start as “scratch runners,” meaning they have to pass every runner on the course ahead of them to earn top finishes.
This system can mean that the fastest course time doesn’t guarantee a win, and women and older runners (and young ones) have a good shot at winning. For example, in the 2015 race, 58-year-old winner Brian Pilcher took home the title in 56:56, which was 1:58 minutes ahead of the second-place finish. The fastest time, 49:11, was logged by the third-place finisher, 34-year-old Coloradan Rickey Gates.
But even if you’re not gunning for one of the top finishes—or one of the storied black T-shirts given to the first 35 runners across the finish line—simply participating in the Dipsea is a rite of passage for any Bay Area trail runner. (And for those true gluttons for punishments, there’s also a Double Dipsea, in which runners complete an out-and-back of the entire course for a grueling 13.7 miles and some 4,500 feet in elevation gain.)
Here, insider tips for running the Dipsea Race, whose 106th running will take place on Sunday, June 12 this year.
1. Mail in your registration ASAP.
Every year, about double the entries pour in for the race’s 1,500 spots. Doing well in the previous year’s Dipsea is an almost guaranteed way to get into the next race as an invitational runner, but what about those eager first-timers? They compete for the remaining 750 spots in a number of ways, such as trying to snag one of the first 500 first-come, first-served entries.
Which means that first-time hopefuls make a mad dash for the post office right after registration opens up (this year, it’s on March 15, at 4 pm PDT). Check the website for more details on the entry process, but race organizers recommend USPS’s overnight service (no FedEx or UPS, however, which do not deliver to the race’s P.O. box). And don’t be afraid to get creative with an accompanying letter to the race committee (more details on that below).
For those who don’t get one of the first-come, first-served spots, take heart: Another 300 spots are chosen at random. Finally, anybody with deep pockets can attend the Annual Dipsea Race Foundation banquet on the Friday before the race. The event includes an auction of Invitational race numbers to the highest bidders, starting at a bid of $500.
Those who make it into the race are mailed a confirmation card (about 4-5 weeks after registration opens) and have to pick up their race number in person with a photo ID.
2. Don’t be afraid to include a sob story or a bribe.
A big part of the Dipsea’s lore is all the “sob stories” that race organizers encourage applicants to send in along with their entry fee. According to Dave Albee, race committee director, committee members all read the letters—some of which are accompanied by gifts like a bottle of wine or chocolate—and collectively decide which ones deserve preference. The kind of story that catches the committee’s eye, Albee says, is from someone “who has had adversity in their life and wants to overcome it, and this race is meaningful for them in terms of overcoming those challenges.”
In addition, there’s the not-so-discreet strategy of making a monetary donation (which, if the entries are accepted, go toward trail maintenance). “I don’t want to use the word bribe, but if someone sends in more than the entry fee, that gets our attention,” Albee says.
Barry Spitz, author of Dipsea: The Greatest Race and the race announcer for 34 years, offers another tip: “If you show that you have contributed to the running community, you should definitely mention that.” Spitz adds that he's heard situations where race organizers have put some top runners into the invitational category. “So people should not be shy about including their results and say all the great things you’ve done running.”
3. Start hill training now.
The wild, rugged course is one of the most infamous in the trail running community, and you can minimize your suffering by getting in as much hill work as possible. You’ll need it to tackle such challenges as climbing 688 steps almost right past the start (the equivalent of a 50-story building), as well as hills such as Cardiac, the top of the 1,110-plus-foot climb from Muir Woods to the highpoint of the Dipsea Trail at 1,368 feet, and Insult, the final short but steep hill that comes at around 6.2 miles. Practice going up and down: Your descending skills are equally important to avoiding injury and, if you're gunning for a strong finish, to cutting your time.
And if you don't get into the Dipsea? Well, then you'll be in great shape for another hilly race this spring or summer.
4. There’s a good chance you’ll take a tumble.
As the race announcer, Spitz sees firsthand the carnage the race produces every year. “About a quarter of the runners show evidence of a fall or injury, which is staggering,” he says. “They clearly show blood and dirt.”
Beyond the treacherous course, another factor that ups the injury quotient: the handicapping aspect of the race. Because the faster runners start at the back, they spend the entire race passing the rest of the field—on tight singletrack, which inevitably leads to pile-ups, traffic jams, and jostling galore. It’s all part of the fun and frenzy, but it’s not exactly the recipe for staying on your feet. Says Spitz: “The course itself is all ups and downs, but when you add in the elements of handicapping, where there’s so much passing going on, it takes [the danger] to another level.”
While some veteran racers opt for regular running shoes to help them slide, sturdy trail running shoes are recommended for newbies.
5. Be careful about the shortcuts you take.
In the past, much of the hype around the Dipsea has been its race-approved shortcuts: the secret routes coveted by top runners. In recent years, however, race organizers have restricted the course. Even so, there are three main shortcuts that are approved, generally known as Suicide (at around the 1.6-mile mark, a seriously steep section that’s only open on race day); the Swoop (a narrow, steep descent through a grassy ravine between miles 5 and 6); and a spot near “the Moors” (located after mile 6, along the Dipsea Trail; staying on the trail is more scenic and simpler, but taking the road is faster though it requires knowing where to re-enter the trail twice).
It’s generally a very well-marked course, but if you find yourself running solo and unsure of exactly where a shortcut is, it’s best to stay on the main route.
6. Take a practice run with someone who knows the route.
If you’re not very familiar with the trail, taking a few practice runs before the race can go a long way in easing your nerves on race day. Just keep in mind that some of the shortcuts are only open on race day—and that you’ll be sharing the trail with hundreds of other runners as determined as you are to reach the finish line.