Forget starting guns and flat pavement — the Dipsea Race kicks off with 688 stairs and a grudge match dating back to 1904, when two San Francisco pals bet on who could reach Stinson Beach first. A year later, on a rainy November day in 1905, more than 100 runners lined up for the first official race — and 17-year-old J.G. Hassard of Oakland High School crossed the line first, aided by a 10-minute head start. Cornelius Connolly, one of only two “scratch” (no head start) runners, actually posted the fastest time but still finished second, two minutes behind — a fitting start for a race that’s been rewarding underdogs ever since. It’s been held almost every June since that first running, making it the oldest cross-country trail running event in the country. The 7.5-mile course climbs out of Mill Valley, cuts through Muir Woods, scales hills nicknamed “Cardiac” and “Insult,” then drops runners down a knee-rattling descent into Stinson Beach — a single-file bottleneck so tight that racers end up jockeying just to get around each other on the way down.
What makes the Dipsea legendary isn’t just the terrain — it’s the handicap system. Slower runners and kids get a head start, faster runners chase from behind, and whoever crosses the line first wins, regardless of actual time. That quirk has let 8-year-olds and 70-somethings beat elite runners outright, and it’s why only 1,500 runners are allowed to toe the line each year for safety and environmental reasons. Grab a spot early if you want in — this one sells out fast, and the stairs, as one veteran 12-year-old racer put it, “are demons.”
The Course
Old Mill Park, Mill Valley (Start) — mile 0
Muir Woods National Monument — mile 2.1
Cardiac Hill, Mt. Tamalpais — mile 4.4
Steep Ravine descent — mile 6
Stinson Beach (Finish) — mile 7.5
Notable Champions
Year(s) Champion
1905 – J.G. Hassard (first-ever winner)
1982–1985, 1990, 1994, 1997 – Sal Vasquez (7 wins — race record)
1993, 2000, 2001, 2004 – Shirley Matson
1998, 2002, 2005 – Russ Kiernan
1999, 2003, 2006 – Melody-Anne Schultz
2010 – Reilly Johnson (age 8)
2012 – Hans Schmid (age 72, oldest winner ever)
2013, 2014 – Diana Fitzpatrick
2015, 2016, 2019 – Brian Pilcher
2017, 2018, 2024, 2026 – Chris Lundy
2021 – Mark Tatum
2022 – Eddie Owens
2023 – Paddy O’Leary
2025 – Audrey MacLean
Address: Throckmorton Ave, Mill Valley, CA 94941
Website: https://www.dipsea.org
