The Dipsea is a special race for lots of reasons. For one thing, of course, it’s old. Started in 1905, the Dipsea is the oldest trail race in the U.S. For another, the race covers an odd distance of 7.4 miles and traverses a wildly varying mix of terrain and surfaces as it travels from Mill Valley to Stinson Beach. Then there’s the intricate Headstart system, put in place “so that people of all ages can compete in this race on a more or less equitable basis.” Not to mention, the course itself is more of a suggestion than a requirement. A whole menu of shortcuts and alternative paths is available to savvy racers, with significant time and places to be gained by making the right decisions.

 With the race capped at 1500 runners, it takes considerable resolve just to get in. Indeed, like most aspects of the Dipsea, the entry process is unique and potentially frustrating. For a first time entrant like our friend Tyler Hansen (gray shirt), getting in required enlisting the assistance of a Bay Area relative. By emailing his application to his wife's uncle in San Jose, and having the uncle drive it to a specific post office in Sunnyvale for mailing, Tyler was able to ensure that his was among the first applications to reach an all-important PO Box in Mill Valley. With 500 entries allotted on a first come, first serve basis, prompt arrival to the PO Box is the best bet for a newcomer to get in. In Tyler’s case, the work paid off and both he and his wife received entry to this year’s race.

For a returning runner, like rabbit’s Community Manager Jeffrey Stern (green shirt), the story is different. By finishing among the top 450 runners in the Invitational Section in 2016, Jeff automatically earned himself entry to this year’s race, which will be his ninth consecutive running. As a Mill Valley native, Jeff knows the Dipsea inside and out and has a special passion for the race, often proclaiming that he knows where he’ll be on the second Sunday in June (when the race takes place) for the rest of his life. In fact, Jeff’s love of the race is a large part of what inspired Tyler to sign up for the Dipsea.

Tyler is what you would call an accomplished runner. Last month he ran a 2:36:57 at the Boston Marathon for a PR in tough conditions. He is a champion on the trails, having won Santa Barbara’s brutal Nine Trails race, and a crusher of 5ks. Tyler is a smart and disciplined runner, a high school cross country coach who knows the sport intimately. For all of these reasons, Jeff thinks that Tyler has a great shot to win the Open Section in which he will be running. The Open Section is for runners who have not earned their way in with a prior performance, and Open Section runners face the disadvantage of starting at the very back. In order to place high enough to earn their way into the Invitational Section, Open Section runners must pass the large number of runners who will have started ahead of them.

 For Invitational runners like Jeff, the situation is somewhat better, although passing remains a key skill. As a 30 year old male, this is Jeff’s last year in the scratch group, which receives no head start. Everyone in the section who is not a man between the ages of 19 and 30 will already have started the race, some with a head start as large as 25 minutes. If you have an ambitious race goal like Jeff does, you’re going to have to pass hundreds of people to get there. Jeff spends a lot more time racing bikes than running, but he runs pretty well for a dabbler. His Dipsea time has steadily been dropping and last year he placed 99th in the Invitational Section, which earned him the honor of a preassigned number for this year’s race. In 2017, with 99 on his chest, Jeff is looking to one-up that accomplishment by finishing in the top 35. That would earn him a coveted black shirt and nearly unsurpassed bragging rights among his Marin County friends. While it may seem like a big jump, Jeff has been running more than ever this year and a recent 5k PR of 17:06 points to the fact that he is in the best running shape of his life.

Because the Dipsea is such a specific race, Jeff and Tyler both believe that it demands some specific training. Early in the course, racers encounter long, steep staircases. The runner who is not prepared for this will face quite a shock to their legs. Likewise, staircase descents are treacherous but must be run quickly. The stadium workout you see here provided the perfect opportunity for the guys to practice both skills. They did 10 x 400 meters at a moderate effort, with one hard set of stairs between each lap, in a total of about 34 minutes. Both agreed it was a solid workout and Jeff pushing the pace on the way down was an eye opener for Tyler about what a fast run at the Dipsea will require. 

We’ll catch up with the guys next week for another workout and more about this fascinating race, and we'll follow their stories through race day on June 11 to see how it all turns out for our friends. If you're already starting to get Dipsea fever, be sure to keep an eye out for invaluable insider tips from Jeff in the weeks to come!