The Best Sports Moment of My Life

The 2025 Dipsea Race

Jun 11, 2025

I’m flabbergasted, astounded, thrilled and humbled by the fact that I broke the Dipsea course record for 90-year-olds yesterday that was set by the legendary Jack Kirk, the “Dipsea Demon” in 1997. Jack’s time then was 2 hours, 16 minutes, 49 seconds. My time yesterday was 2:15:15.

Not only that, but they awarded me the Jack Kirk “Dipsea Demon” award. I couldn’t (and cannot) believe it.

Jack ran the Dipsea 68 times, from 1930 until 2002 — from ages 24-96 — and won it twice, and is the race’s patron saint.

The Dipsea Race is the oldest trail race in America: it starts in Mill Valley with 671 steps up the mountain, an elevation gain of 5-600 feet, then a run downhill to Muir Woods, across a creek, and then — up and up and up, boulder-hopping, root-dodging, onward toward your goal of Stinson Beach.

It’s tough, beautiful, difficult, local, and romantic event. It’s called by Dipsea historian Barry Spitz “The Greatest Race.” There are hundreds of people who are into it on a deep level.

Handicapping for the race is unique. The older you are, the earlier you get to start; women get to start earlier than men. For example, a 74-year-old man gets a 25 minute head start, as does a 66-year-old woman. Scratch runners — 20-25-year old guys — get no head start minutes. Women ages 26-39 get a 9 min. head start. *See chart in NOTES below.

** There was an article on me in the San Rafael Independent Journal by DerekWilson the day before the race. (See NOTES below.)

Black Shirts

The top 35 runners get a black shirt each year, and they are much sought-after and prized.

In the old days, I was heavy for a trail runner (156 pounds at 5 ‘-7”) and my uphills were slow, but I learned some good downhill techniques that allowed me to run fast (and have fun!) on the downhills and steps. This got me 10 black shirts in the 19 times I ran the race (from ages 52-75).

Getting Into the Race This Year

It’s not easy — they get about twice as many applications as there are spaces in the race (1500). Plus, I had not run it in 15 years.

I sent off my application, referring to the black shirts, and lo, they let me in.

I didn’t really train other than pushing it on weekly hikes with Tomas (and a couple of brisk 6-mile walks in SFO with Joe).

I got some good Hoka trail shoes and ran the course 3 times in 2-week intervals, and man was it hard! 3 hours, 10 minute the first run, and I was wrecked. The Dipsea trail just kicks your ass (although at the same time, it rewards you with mountain beauty).

Apparently what I did was right this year — I rested between workouts. (Jeff Galloway says the best way to improve your running time is to avoid getting injured.)

As incentive, I had Jack Kirk’s times posted above the kitchen sink:

2:16 at age 90 seemed an impossibility. I thought maybe at age 92 I could catch him.

I started with a bunch of other people in the AAA Group (75 and older men), with a 25-minute head start.

Tomas told me I would run faster in the race because of all the people, and it was true. Jakub showed up and coached me down the Moors and I did some of my old downhill cruising in a scaled-back mode.