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The Dipsea is the 2nd oldest foot race in the United States. It was the result of a wager of San Francisco's Olympic Club that was made as to who could make it to the Dipsea Inn first. The challenge proved so exciting that club members decided to make an annual race of it. The first one was held on November 19, 1905.

The course begins in downtown Mill Valley with a sprint down Throckmorton to the Old Mill Park, then up three flights of stairs as tall as a fifty-story building, and up some more through an old horse ranch to Windy Gap. Then it plunges down into Muir Woods across Redwood Creek and begins a tough grind up through the trees over trails named "Dynamite" and "Cardiac." At the top of Cardiac, the course levels out before it plunges down through the "Swoop", over the rocks and roots of "Steep Ravine" and the discouragingly steep climb up "Insult Hill." Finally, as the course follows the relatively gentle slope of The Moors toward the ocean, Stinson Beach is in sight a mile ahead. This is where experienced racers resort to secret shortcuts and where others racers will sprint the last quarter mile in an effort to move up a couple of places in the final results.

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