Running the Dipsea: America’s Oldest Trail Race

Get full access to Outside Learn, our online education hub featuring in-depth fitness, nutrition, and adventure courses and more than 2,000 instructional videos when you sign up for Outside+.

As we drive to the start line of the 100th Dipsea race, my dad launches into one of his inspiring father-daughter pep talks. “It’s a shame you couldn’t run faster last year,” he says to me, smirking, as he pulls into Mill Valley, California. “If you’d laid off the chalupas, you could be in invitational with your old man.”

It’s a sore spot. After my slow performance last year–a 7.4-mile death march is more accurate–I’d been unceremoniously demoted from invitational to the less prestigious runners' division. My training then–a strict regimen of gummy bears and strolls to the grocery store–had not especially paid off on the steep grades and jagged singletrack. And while I’d prefer not to go into details, by the time I’d staggered across the finish line, pictures show I bore a striking resemblance to Whistler’s Mother

Once I recovered, I vowed this year would be different. I’d trained my ass off at high elevation, kept my chalupa count down, and minimized my couch time, all for the sole purpose of seeing my dad’s face when I crushed him at the finish line.

The Dipsea is the oldest trail race in the U.S., and since its beginnings in 1904, it's had a history of fierce competition beneath its sunny veneer of family, friendship, andfun. It began as a grudge race between two buddies, Al Coney and Charlie Boas, who started at the Mill Valley depot and ran off to see who could clear Mt. Tamalpais faster. It didn’t matter which route or shortcuts each used, so long as both men ended up at Stinson Beach. Boas won. Naturally, Coney wanted a rematch. Most historians will tell you the race proved so “exciting” over one hundred men signed up to compete the following year.  But this ignores the greater, more complicated question. Why such a draw?

A newcomer to Dipsea might mistake the tame-looking Sunday crowd of affluent elderly types, parents, and small children for a bunch of harmless Marin hot-tubbers. But don’t be fooled by the facade; this pack of competitors is one of the saltiest in the lower 48. Run enough Dipseas and you’ll soon recognize the cherubic seven-year-old as the veteran road warrior who will burn you in the chute. And that smiling grandpa stretching in the purple jumpsuit? He’s really sizing up the crowd with vulture-like intensity. These people aren’t here to mingle. They’re out for blood.

A unique system in place since 1983 varies starting times according to age and gender, so racers as old as 70 and as young as eight have claimed victory here. There are also two waves of competitors–invitational and runner–and the race allows participants to take short cuts throughout the course. All of this makes for one of the kookiest, most suspenseful races in the country.

When the gun sounds, I’m off. Whether its the altitude training in Santa Fe or my wounded pride, something is working and I'm covering ground fast, like a moderately graceful, somewhat stocky mountain goat. After 15Dipseas, the course is etched in my mind, starting with the more than 680 stairs that look to be from an M.C. Escher drawing, to the root-riddled climb through Muir Woods, and the slow grind up Medevac-worthy Cardiac. And then, for a moment, there's the dazzling, hazy, salt-perfumed greatness of the Pacific Ocean spread out underneath like a dream. Butit quickly disappears on the way to the ankle-snapping potholes of Swoop’s Hollow and Steep Ravine. Even as I fight the urge to puke, I know I’m the closest I’ll ever get to flying. And that's when I understand. I've found what Dipsea runners have sought since the beginning; proof I am worthy of the mountain. I catch the briny smell of  kelp and go for the final push down Highway 101 to the parking lot of Stinson Beach. At the chute, among the  crowds my dad is waiting for me. I show him my stopwatch.

“No way,” he says, before swearing. I’ve beaten him by six minutes. When I tell himhe should lay off all those PBRs, his eyes darken. It’s the indignant look of a beaten fighter, the kind of look that, at another point in time, might have launched a hundred years of racing. His expression tells me I’d better celebrate now, while I still have the chance. Because next year is a whole new story, and I’ve awoken my competition.

–Shauna Sweeney

Top photo: The coveted Dipsea black shirts that go to the first 35 runners; middle photo: Reilly Johnson, 8, youngest winner ever of the Dipsea, and seven-time Dipsea winner Sal Vasquez; bottom photo: Runners gather for the awards ceremony at the foot of Mt. Tamalpais (Photos by Shauna Sweeney)

Filed to:

promo logo