First held in 1905, The Dipsea Race is the longest running trail race in America. Stretching 7.4 miles from Mill Valley to Stintson Beach, CA, The Dipsea snakes over Mt Tamalpais offering a beautiful perch over San Francisco. Known for its stairs and vertical challenge, The Dipsea is a classic for trail runners worldwide. Local standout and johnny come lately, Jeffrey Stern looks back and looks to put a stamp on the race.

Words by Jeffrey Stern:
I ran as a kid, but never seriously. A few laps around Boyle Park in Mill Valley was probably my first mile, at age 5 with Coach Jim, our Park School Elementary PE teacher. As I got older, we ran loops of Bayfront park along the fingers of marshland stretching out from the San Francisco Bay. I tried middle school cross-country for a year, but it never stuck.

Running didn’t captivate me as a kid. I was good it at, I had natural speed my coaches always told me, but baseball and in particular, stealing bases was my thing. There’s nothing like the thrill of sprinting towards a base and diving head first in attempt to gain 90 feet, a whole 25% closer to scoring a run. During the 2005 season, my senior year at Tamalpais High, I did snagged a perfect 26 of 26 bases in 25 games.

I hung up the spikes, dusty uniforms, and ball caps of my youth for boards; surfing, skating and snowboarding, I essentially carved my way through college. By my last semester, I began to commute by bike to class, and even recall lacing up my shoes for a handful of jogs around local trails. Perhaps the Dipsea was calling already and I didn’t know it.

Soon after, I was bit by a cycling bug so strong that I threw my whole existence into the sport — my time, my life and friends, travels around the world, even my jobs. For a few years, it felt like my life was to get paid to ride bicycles, eat good food in prolific amounts, and interact with other cyclists in some of the worlds most beautiful places. First the mountain bike, then along winding coast roads from Mallorca to Taiwan. It was awesome and I felt lucky. I followed my heart and I called it my passion, for a time.

I felt a new urge to pursue something different. I had achieved a lot of goals on two wheels and it felt like anything further was unrealistic. A high speed bike crash was enough to convince me to step away. I was compelled to get back to the trails with just my own two feet. I had casually jogged to the tune of 100 or so miles per year for the last decade. Trail running to be more specific. The one element of baseball that I loved and excelled at so much in my teenage years, combined with my endurance from thousands of miles on the bike and ultramarathons just made sense.

In the past 12 months I’ve run nearly 2,500 miles and ran four ultras, sandwiched between another ten foot races; not that much when compared to the greats of the sport, but quite the change for me. Over the last seven years I’ve ridden my bike 50,000 miles but run just 500. Those 500 miles, enough to just survive the Dipsea and stagger around in crippled with pain for days afterward.

This year that all changed. I hired a coach for the first time, I’m cross-training with intent, and take nutrition and recovery very seriously. I know the benefits of wholesome eating as much I do interval training and proper rest. My athletic pursuits appear to have finally come full circle in the last quarter century. Something I’d never predicted, definitely not down a linear path, but along a sinuous path just like the Dipsea itself.

One of many sections of stairs found throughout the Dipsea.

On Sunday, June 10th for the first time in my life and on my 10th consecutive attempt, I’ll line up at the 108th Annual Dipsea Race finally feeling like a real runner — I feel is my true calling as an athlete.

Running now means so much more because I waited. I know that everything I’ve experienced has prepared me for this exact moment, the day I realize a dream I’ve had for a decade. It marks the start of a new chapter of Dipsea streaks, achieving goals never thought possible, and coming back with the drive to keep reaching for more.

Family, friends, dogs, health — there are really only a few things more important to me than the race itself. It’s likely more than coincidence that those are the same elements that make the yearly pilgrimage back home and then onto the starting line in downtown Mill Valley all the sweeter with each year. All in hopes of creating my own personal Dipsea dynasty, even if I started at it a little late, I think there is plenty of time to make it happen.