The Dipsea Experience

Will Chase

The sand stung our faces as the first helicopter touched down on the beach. Its red fuselage dipped below the horizon of the small stand of trees between us and the beach, and the paramedics ducked, turning their heads to avoid the whipping sand. Once the raging rotors slowed to a tolerable level, they hustled the first of the competitors into the gaping side door of the medivac, taking care to keep the stretcher steady. Having secured the patient into the helicopter’s gurney, and with the IV bags hung, they slammed the door shut, gave the thumbs up, and ran. The rotors roared to life, sending a fresh blast of projectiles our way.

This process was then repeated … seven times.

I shook my head and thought to myself, “this is just a race. Eight medivacs for a running race?”

The Dipsea

My girlfriend and I recently ran one of the oldest and toughest races in the US … The Dipsea Race. I’d heard about this race over the years, and chalked it up to a bunch of nut-balls trying to kill themselves on an otherwise nice hiking trail.

Living in the San Francisco Bay Area, you’re bound at one point or another to become familiar with the Dipsea Race … it’s the second oldest running race in the US, after the Boston Marathon. It’s also one of the more coveted races in which to participate. And with all the potential for personal bodily harm, strong competition, storied history and odd rules, it garners some press.

The race is 7.1 miles, give or take (more on this later). Now, 7.1 miles is no big deal … it’s what happens in the course of that 7.1 miles that’s the hitch. First off, you’ve got 2,200 feet of elevation gain. This includes 676 stairs (that’s a 50-story building to you and me); sickeningly steep, winding, dusty single-track; quad-killer, never-ending, debilitating climbs up root- and rock-strewn trail; and spine-crunching downhills on rocks, roots and stairs that would make chiropractors smile with anticipation of putting their kids through college.

In short, this is not a running trail … it’s a hiking trail. The only things that should be running on this trail, realistically speaking, are deer. And yet, this is my all-time favorite trail to run. With so much variety to the course, and unadulterated beauty, vistas, challenge, mystery, options, twists, turns, and bushwhacking, it’s pure entertainment the whole way. Sometimes you feel like you’re flying, sometimes you feel like you’re mogul skiing, sometimes you feel like you’re a marine blitzing through enemy territory, and … well … sometimes you pretty much feel like you’re going to either pass out or puke. And that’s what turns a run into an adventure.

Race Format

Assuming you’re able to wrangle your way in, you’ll find that the race itself has what you might call a non-standard format. Now, here’s where things get complicated, so buckle up. The race is run on a staggered handicap basis, according to age and gender. The older and very young participants go off first, followed by successively “faster” age and gender groups in one-minute increments. The last to go out are the strapping young men in their 20’s, a full 22 minutes after the first group goes off. The whole idea here is that the race gives equal opportunity to all runners, despite your age or gender (a 12-year old girl won it once; 3-time winner Shirley Matson is 61). And as always, first one across the finish line wins.

There are two sections to the race: the Invitational Section and the Runners Section. The Invitational is for those who were invited back because they performed exceptionally in previous years, where the Runners Section is for the rest of us. In the race, the Invitational group goes first, all starting off in order of their handicaps. Then, the Runners Section goes, in the same handicap order.

So, if you do the math, I (a 34-year old male) was running in the second-to-last group in the Runners Section, a good 44 minutes after the first group took off for the finish line. I had to come in the top 750 overall to qualify for the Invitational next year, and I was starting from the caboose. I had over 750 people to pass. I was screwed.

Race Day

Running the course is one thing… running it with 1500 people in front of you, 750 of whom are officially in your way, is altogether another thing. On race day, we headed out from San Francisco up over the Golden Gate Bridge to Mill Valley. We parked on a secret side street, took a secret short-cut alley to the start line, and made good use of a secret Port-a-Potty along the way. The line to the Port-a-Potties at the start line was daunting – this race is all about insider information.

After munching down an energy bar, I tossed my backpack into the big yellow truck that would take it to the finish line. Suddenly, I turned to see Jack Kirk standing next to me. Jack (known as “The Dipsea Demon”) has run this race for 67 consecutive years. At 95 years old, he runs – well, walks – the course in about 4 hours or so, but damned if he doesn’t get it done. As the oldest runner in the race (in case that’s not patently obvious), and a 2-time former champion, he starts first in the Invitational Section. So, basically, everybody in the race – 1,500 people – passes him at break-neck speeds on this vicious course. The race instructions actually request that you don’t pat The Dipsea Demon on the back as you pass him.

Jenny and I turned to get a look at this man, this 5’2″ phenomenon. He was dressed in old khaki pants secured about his fragile-looking waist by a knit cloth belt. His white button-down shirt offset his white hair, and his simple Keds-like sneakers rounded out the curious package. He was just kind of hanging out, with his hands dug into his pockets, smiling affably. Somebody said to him, “Say Jack, we’ll let you go first today, OK?” Jack replied without missing a beat, “Doesn’t matter to me,” and everybody within earshot got a good chuckle out of it. Let’s just say I’ll consider it a monumental accomplishment if, at 95, I’m able to say the words “Doesn’t matter to me”, about anything besides the color of my coffin … let alone run the Dipsea.

The Start

I watched the Invitational racers taking off, group by group. It was a pretty interesting cross-section of runners, young and old, all manners of attire and attitude. Team uniforms, shirtless, water bottles, bandanas, trail shoes, running shoes, racing flats. Some serious, some at-ease, some having the time of their lives as their friends, family and neighbors lined the start chute, cheering wildly as each group took off, minute-by-minute.

With the invitational runners off, it was our turn. Jenny lined up with her group, and she was off. Soon enough … well … 8 minutes later to be precise … it was my turn. I lined up, the yellow rope hovering before my chest dropped, and I took off, thinking: “You have to pass 750 people. Leave it all on the trail.”

The Stairs

I started to feel the nerves shaking off, as I focused on my running – down the road, around the corner, through the little Live Oak Park, and up the short road to the stairs. I looked up. From the bottom, you can see the entirety of the first flight of about 300 or so stairs. They were jammed *solid* with people, three wide, top to bottom. Everybody was walking them, one at a time. Now, there’s a very small 6-inch sliver of extremely steep, slippery, leaf-covered dirt right next to portions of the stairs. Any chance I could get, I’d jump onto this little strip, and grip with all my shoes could muster, and just keep my head down and RUN.

I was passing bodies by the hoard. One guy actually shoved me off the stairs entirely, and drew the ire of those around him. All’s fair, I thought, well, now it’s my turn … as I ducked under the arm of one guy and squeezed between two people to pass. And again. And again. There’s a hole, get into it, run harder. Duck your shoulder, slide your arm through, then your head, go low, and lift your hand up to squeeze through. These were not people anymore, they were anonymous, faceless body parts that were IN MY WAY. It was like running through a meat packing factory, with sides of beef hanging on runners, and I’m keeping my head down, watching the ground, and pushing through everything I hit. This was more akin to football than it was to running. So be it.

I did this for the three flights of stairs, and somehow managed to not fall once. Giving a quick thought to how many people I probably just passed (though it was nearly impossible to tell for sure), I turned right on the Panoramic highway and headed up through the neighborhood — formerly a horse farm in the early days of the Dipsea – on steep paved road, transitioning into fire road. I could get into a rhythm up to the first peak, and catch my breath a little. The words “pass people” kept drumming in my head, over and over. See somebody ahead of you, pass them. Don’t get complacent. Don’t settle for sitting behind them. Pass.

Windy Pass

I peaked out at the top of Panoramic, crossed the road, and girded myself for the first downhill blitz through Windy Pass, a steep winding downhill singletrack interspersed with series of short steps. Rule one: stairs slow you down; avoid them. I had learned exactly where I could skip off to the side of the stairs and scurry down the slight patches of dirt to the next set of steps. Two steps, single track scurry, one step, single track, two steps, scurry, repeat. At the bottom, leap the ditch back onto the pavement.

So I hit Windy Pass, and this time, of course, it was crowded. If I stayed in my pattern, if I went with my gameplan, I’d be stuck behind people the whole way. Had to improvise.

I started the “On Your Left” chant, trying to get people off to the side so I could blaze through. Many don’t listen, or assume they’re as fast as you are, and ignore you. So it became less of a kindly request as a panicked “I’m out of control and I’m going to take you with me” screech, which got their attention. The main problem running this kind of trail in a crowd is that you cannot see those steps are until they’re under your feet. Be flexible, absorb the shock. Keep your feet moving fast. Stay balanced. Take it, however you can, whatever it takes. Skid down a few of them, hold onto somebody’s back and pray they don’t lose it. Feel the guy’s hand on your back, and hope he doesn’t lose it, too. Try to remember where those steps are, when they’re coming. Remember what I said about mogul skiing? That’s mogul skiing … wearing a blindfold.

At the bottom of the Windy Pass section, where the trail meets up with the Muir Woods Road, you can take a quick left down a set of about 8 stairs that lets you out nicely onto the road, or you can go straight and jump the ditch and (hopefully) land on the far side. As always, I took the ditch, timing my jump, and pushed hard to make it in stride – and without blowing out a hamstring. Just as I planted my launch foot, I felt a hand on my back. Uh oh.

Anybody with their hand on my back when I’m making my plant to jump is simply not going to make it … they’re too far away … they’re dead meat. This guy was following me without a clue as to where I was headed. As I lifted into the air, I could feel this hand scrape desperately down the length of my back, and hit the heel of my shoe. As I landed and quickly turned right onto the road, I heard a sickening splatch sound. I whipped my head around to see him sprawled face-first on the pavement, and thinking “ow”, I accelerated down the road. This was every man for himself.


Muir Woods Road winds down a gradual hill into the Muir Woods National Monument. You run on this for about a half mile, where you turn back onto singletrack. Half way down the singletrack, you see a couple signs. One sign points right and says “Easier” in green, while the other points left and says “Suicide”, in red.

I chose Suicide, the steepest, dustiest and most slippery stretch of trail on the course. At high speed, you’re pretty much out of control, moving your feet as fast as you can, keeping your balance as centered as possible, and trying not to cartwheel into the thick brush around you. I somehow managed to pass a couple people (this was not part of the plan) as I tore down it arms flailing, grabbing the outstretched branches of bushes to slow me down, or keep me upright, or something. One guy in front of me panicked at the sound of me bearing down on him, and scooted to the side to let me by. Rule 2: you can use other people’s sense of self-preservation to your advantage.

Muir Woods

The trail let out onto the lower parking lot of Muir Woods, a park known for its beautiful redwood groves. This was the bottom of the course, a brief and rare stretch of flat before pounding up another 1100 feet of elevation. Turning onto the last set of stairs down to the bottom of the trail, the creek came into view. The creek is about 12 feet across, and ankle-deep. There is a one-foot wide footbridge across it that everybody takes, and it’s renowned for getting clogged up with runners. After the footbridge, the trail takes a sharp right turn before heading up Dynamite Hill.

My girlfriend and I had studied the creek earlier, and realized that we could just blast through the water, avoiding the backlog on the bridge, and cutting the corner on the right turn. Every little bit counts. Our only concerns were whether this was a legal shortcut (if you’re seen taking an illegal shortcut, you will be disqualified), and whether we’d snap our ankle on the loose, grapefruit-sized rocks just below the water’s surface.

After some practice the day before, I knew every step to take. I had resolved to look for park rangers or race officials when I got to the stairs, and if I saw any, I’d take the bridge; otherwise, I’d go for it. Turning the corner, I didn’t see anybody, so I blasted through the water, splashing loudly. I heard somebody on the bridge exclaim “Whoa! What the hell?! Did you see that?” as I passed 10 dumbfounded people.


The adrenaline spurred me as I started the brutal climb up Dynamite Hill, which was absolute gridlock. Dynamite Hill is about 1 mile of double-track trail strewn with precarious rocks, roots, stairs, twists and turns. And it’s really steep. People were trudging up two and three across on it, and no amount of “on your left”-ing would get them to move. But I was impatient, if not panicked. Whenever I could, I employed my newly learned football techniques. Unlike the stairs, people on Dynamite were afraid to move out of the way, because they might step on some harrowing terrain. As a result, Dynamite felt more like a rugby scrum.

Every chance I got, I jumped on small side strips, clamored over low bushes and grasses, ducked under people’s chugging arms, yelling “on your left” every few steps. At this point, I was feverishly determined to qualify … if not for the thrill of accomplishment, but because I sure as hell never wanted to go through this again.

Dynamite is an absolute grind, and it psychologically wounds you, since you know there’s still worse terrain to come. There isn’t much to look forward to, and at this point you’re starting to fantasize about water as your mouth turns to cotton.

At the top of Dynamite, the course levels out a bit onto the Hogsback, a mixed bag of fire road and single track, often both running in parallel. Now and again you can catch beautiful glimpses of the ocean across the rolling fields of golden grass, tantalizing you from afar. When the sun’s out, it beats down on you without remorse, and it was particularly bad the day of the race. The heat was suffocating.


There’s a sort of elation as you approach the base of Cardiac Hill. The long, slow climb to the base levels out, and gently dips down into the cool forest, giving your suffering quads a short but welcomed respite, as you are cooled by the shade of the trees.

Cardiac is a relatively short hill, yet it’s the most technically challenging. Here the roots are massive, the trail extremely winding, and the rocks treacherous. Several series of steep steps provide some sanity in an otherwise piecemeal terrain. Here, you focus on placing each step, and doing so with concentration, confidence and power. A false step could take you down before you knew what hit you. It’s a crushing hill.

Rounding the corner to reach the top of the course, a nice-sized crowd cheered runners (and walkers) cresting the hill in various states of disrepair. I grabbed water from an outstretched hand, my eyes raking the crowd in an almost hallucinatory state, pinched the cup and stumbled grotesquely as I tried to drink it down. It’s all downhill from here.

The Swoop

Usually, I hit the downhills of The Swoop strong. But I was pushing as hard as I could today, and my legs just weren’t going. My stomach felt a bit queasy and my legs were a bit rubbery. Putting it out of my mind, I threw my legs out in front of me as fast as I could, and headed into the steeper, rockier downhills with my usual lack of caution, allowing my feet to run out Road Runner-ish below me, pulling forward with each footfall.

Down and around the twisting trails of the Swoop, I reached one of the key shortcuts. It’s a left turn, identifiable by a 3-foot high wooden fence that you must climb, clamor, or jump over, dropping you into treacherous, fast deer trail. Being careful to keep my feet going fast, one in front of the other (this trench of a trail is only about 8 inches wide, and sloped on either side, so a misstep will turn your ankle in a heartbeat), I somehow managed to pass a few more people.

Steep Ravine

The bone crunching stairs of Steep Ravine, taken at speed, will shake the teeth out of your head. It’s smart to run with your mouth closed and your tongue inside, lest you bite it off. These are small, winding, varying, 5 inch railroad tie stairs, with pockets of dirt just inside the railroad ties. This makes for a precious little landing area on each step, and the potential for skittering down several steps at a time, turning your ankle, or worse is … well … very high.

I take these steps 2 or 3 at a time, as fast as possible, teeth clenched tight to prevent my brain from rattling against my cranium, and crunching my abs to keep my organs from getting scrambled. Every bone-jarring footfall pounded my wrenched stomach.

I passed several more people, who were intelligently taking these perilous stairs with caution, and equally intelligently, were staying out of the way of the nutballs hurtling down towards them from behind. “On your left” became a polite aside on the steps, since it was vastly apparent to these poor hapless people that they were in some serious danger. I actually felt sorry for some of them … it can’t be fun being constantly shoved around on the trail.

I crossed the footbridge over the creek at the bottom of Steep Ravine and headed up Insult.

Adding Insult to Injury

The aptly named Insult Hill is a short but steep climb that comes on the tail of the bone-crunching downhills of Steep Ravine. It’s the final insult that the Dipsea throws at you before spitting you out the end of the trail. It’s the last psychological barrier to overcome, and it feels like the trail is laughing in your face one last time.

OK, so remember way back when, I mentioned I ate that energy bar before the race? OK, so this is where it comes back into play. After cresting Insult, I took the right turn onto the fire trail, huffing, heat nailing me, stomach churning, making those old familiar statements of protest. “Ohhh no,” I prayed to the running gods. “Not now. Please not now … not after all this work.” No choice. Without breaking stride, I aimed right and wretched into the bushes alongside the trail. “Augh. What’s this going to do to me?” I thought, fighting to keep my pace up. I was not going to let this beat me.

The trail again meets up with Panoramic Highway here, and heads down the final pitch towards the beach. I made the turn onto the road, which was split down the middle by orange traffic cones so that car traffic could have half the road. As I reached the road, I threw up again. I was groaning an apology to the poor guys behind me when I noticed a car to my right, the driver staring at me, mouth agape. I got a good chuckle over what he must have seen: guy running onto the road from a trail, staggering, throwing up, and running harder. Niiiice. Poster child for running.

Panoramic Shortcuts

With that out of my system, I felt better and pushed my pace. I shot left off the road and onto the 8-inch wide deer trail that acts as a shortcut, shooting straight down and linking up the winding switchbacks of Panoramic Highway.

Down through the last bit of twisty, rocky, rooted singletrack, I followed close-on a few guys, and managed to pass them by jumping down the final sets of stairs while they took them one at a time. At the footbridge at the bottom of the trail, I was faced with some race officials telling us to stay to the left of the bridge. Somebody had taken a pretty serious header and lay sprawled on the bridge, making unhappy sounds as the paramedics huddled over his contorted body.

Down the Stretch

Down around the corner, and onto Route 1, I was on the final sprint down to the finish line. I turned towards Stinson Beach, and saw the final 300 yards lined with people, 10 deep, cheering on the runners as they passed. I had no idea how many people I had managed to pass, no idea of where I was in the pack. So I forgot it for a moment and just enjoyed the adrenaline from the cheering crowd as I cruised down the straightaway towards the big “Dipsea Finish” banner ahead.

There was a group of gloved volunteers, catching people as they came through the finish. I looked up at the guy who caught me. He read the question in my eyes and said “I think you qualified.”

There are simply no other words that could have been more welcome at that moment. I kid you not, tears welling up in my eyes, I damn near kissed him. I still couldn’t believe it, though … I wanted to see it in writing, on an official list, before I could really get my hopes up.

But regardless of what the results might be, I knew one thing for sure. I sure as hell didn’t want to do that again.

The Aftermath

We wandered through the finish area, grabbed any liquid we could get our hands on, donned our official Dipsea Survivor T-shirts (highly ironic today), and shared stories with friend after friend. There had been excessive heat that day, and both experienced competitors and neophytes alike had succumbed to its grip. There were twisted ankles, broken legs, concussions, heat exhaustion, and the usual assortment of bruises, scrapes and scratches. A former Dipsea champion had crumpled to the ground just before the finish, and had to be carried across the line. It was a brutal day for most competitors.

As for me, a little worse for wear, I came in #721 overall. I qualified. I still don’t know how I did it. Somehow, though, I did … with 29 people to spare. And so next year I will run in the Invitational.

And after all the awards were given out (including the coveted black shirts for the top 35 finishers), all the speeches given, and most of the food consumed — almost 4 hours after the whole thing got started — Jack Kirk made the turn onto the last stretch to the finish line. The entire crowd ran to line the full 200 yards of that stretch, to laud this indomitable man as he ambled towards the finish line. Smiling and waving, he made his way through the cheering crowd, and grinned at the innumerable flashbulbs, as he shook the hands of little kids whose parents pushed them out to touch this legend who made his name in this incredible race.

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