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I can’t pinpoint exactly when  I caught wind of the fabled Dipsea trail and its eponymous point-to-point race from Mill Valley to Stinson Beach, but it was before I moved to San Francisco, and I knew that it’d be one of my first challenges after I relocated.  The statistics alone fascinated me:

  • 103 annual runnings and counting
  • 7.1 milles
  • 2300′ feet of climbing
  • 688 stairs (the equivalent of a 40 story building)

If a single Dipsea crossing isn’t enough, the race also comes in Double and Quad variants – classifications Taylor and I typically reserve for Belgian beers.  The latter is particularly grueling: four passes that include 160 stories worth of stair climbing, the same number of floors as the Burj Khalifa – the tallest manmade structure in the world.  Clocking in at 28.4 miles, and 9276 feet of elevation gain, the Quad is technically an ultramarathon, and if the course isn’t punishing enough, the race falls on the Saturday after Thanksgiving.

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Never one to shy away from a challenge, I registered for the Double Dipsea not long after I moved to San Francisco from New York City.  I ran on the Dipsea several times a month to train for Escape from Alcatraz and Boulder 70.3, and figured that sandwiching the Double Dipsea in between both races was only fitting.  Having never run a trail race, I was nervous about making my debut on a strenuous course, let alone a local-dominated race where many of the entrants utilize the allowed shortcuts.

It was during that race that I learned the value of picking my battles (hills) and only running up hills that wouldn’t spike my heart rate to the point of no return.  I soaked in the scenery, was encouraged by the camaraderie, and reveled in the low-key atmosphere surrounding the race.  By the time I crossed the finish, the pain rivaled my first road half-marathon where I couldn’t fathom doubling the distance one day.

Double Dipsea 2011 - my first trail race.  Still wearing my North Face Single Tracks.

Double Dipsea 2011 – my first trail race.

That day is now, and only months after breaking the tape at the Double Dipsea again with Taylor in June, I’m 30 days out of my first Quad Dipsea.  A week later, we’ll be making another crossing as part of the North Face Endurance Challenge 50K on 12/6.  Few things are for certain, but my massage appointment on 12/2 is one of them.