Running & Good Times

Running the Dipsea…Trail

History of the Dipsea

 According to, “One summer day in 1904, several members of San Francisco’s venerable Olympic Club set off for the Dipsea Inn, which had just opened on the Pacific Ocean sand spit now called Seadrift. They took the ferry to Sausalito, then the train to their starting point, the depot in Mill Valley. A wager was made as to who could make it to the Inn first. The challenge proved so exciting that Club members decided to make an annual race of it.  The first race took place on a rainy day on November 19, 1905 with more than 100 runners lining up at the starting line waiting to etch their name into the history books.”

Dipsea Stairs.JPG

I first heard of the Dipsea Race about four years ago when I was visiting my in-laws.  Someone had mentioned I should run the Dipsea.  Their description of the race sounded really crazy and I was intrigued at the potential opportunity.  After doing some research, I discovered this is a very difficult race to gain entry.

The race is capped at 1500 runners – trail preservation.  Their entry process has not changed with the times – they require a postmarked application.  A select number of runners from the previous year’s race are automatically eligible, leaving the remaining slots open for all sorts of entry qualifications…first come, silent auction, and finally, a lottery.  Entry into this race might require the handshake of a secret society!

My Journey on the Trail

The morning began before the sun had a chance to peak through the Bay Area fog.  This is a dense layer of cloud cover that envelops the San Francisco Bay area.  I was not sure what to expect as I readied my running gear.  I packed minimal running gear during my quick trip to San Rafael, and the two most important items were my Pearl Izumi shoes and my Ultimate Direction handheld.  What more does one need, right?


Nearing the infamous steps, I stood in a small park surrounded by ginormous California Redwood trees.  I found myself looking skyward at these ancient giants, and marveled at their beauty.  Making my way up the hill and out of the park, I could start to see a few of the bottom steps.  The closer I got to them, the more of them I could see… they appeared to be a stairway to heaven.  As I prepared my watch, I took off bounding up every other step.  My strategy before seeing the staircase was to run a couple minutes and walk a minute, and so forth.  Feeling a bit too excited, I was smoked after the first set of stairs.  Every breath I inhaled and exhaled felt like I was breathing fire.  All I could think was, “Shit, what have I done to myself?”  We do not have hills on the East Coast let alone a vertical staircase to the heavens.  It was all I could do to catch my breath and continue the journey.

For the most part, each of the steps was of equal proportion in height and size, but nearing the top, a small section was made rock pieced together forming a step.  I came across another section that was built of wood and with the low light, the steps blended into the surrounding landscape making it difficult to judge their distance.


All along this path were houses that appeared to cling to the hillside.  The locals refer to them as tree houses.  Each one was unique in its own right.


Clearing the final step, I quickly made my way to the actual trail portion.  The trail was not very wide – single-track – and was eroded down the center in some places.  Since it does not really rain during the summer months, and the trail is frequently used, a thin layer of fine powder covered the trail’s surface. That being said, my shoes required a bath afterwards.


More Stairs.JPG

Because of the terrain, there were really no flat areas.  I was either running or walking uphill, or trying to see how fast I could go down.  As I discovered afterwards, certain sections of the trail have been given names over the years (see photo below).  I only went as far as the High Point – hoping to see the beautiful scenery below.  Unfortunately, that was not an option with all of the fog.  Maybe next time.  I traveled approximately six miles before I turned around and headed back.


The route to the top, including my side trek to view the “tree houses,” only took me 1:15:07.  My return trip was much quicker at less than one hour.  The trail record, I found, is 00:42:03.  This would require lots of hill training, something I am not privy to in my current running environment.



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