America’s Premier Trail Races

Dipsea Race

June; Mill Valley to Stinson Beach, Calif.

The oldest trail race in the U.S. delivers a winning trifecta of a challenging course, awe-inspiring scenery, and a quirky vibe. First run in 1905, the route includes climbs up steep steps, rolling trail through redwood and fern forests, tight singletrack and a roller coaster–esque descent to the finish line. Due to course limitations, only a lucky 1,500 entrants get to run the race each year (registration opens in late March and will fill quickly). Podium contenders are anybody’s guess due to a unique handicapping and starting wave system that sends the slowest runners off first and the fastest runners last. This race also accepts “sob stories” from runners eager to be accepted.

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