Even when things don’t work out the way you planned, Vashon’s Passport to Pain, the P2P, is one heck of a ride. As the big ride approached, I realized I had not trained nearly as much as the year before and was poised for a classic sophomore slump. With just a week to go what could I do to improve my chances of finishing? I could shave my legs. I have never adopted the smooth look of a hard core cyclist but thought, “What could it hurt?” I found out. As I stepped out of the shower, I thought I might have to miss the ride due to blood loss. Then the next day I decided to get in a bicycle wreck just in case I’d forgotten how to do that.

So at 7:30 a.m., with one leg scraped and bruised and the other sporting a weird mohawk from my inept shaving, I set off to ride my second P2P. What makes this ride unique is its decidedly irreverent attitude. For instance, when you select which ride you want to do the choices are “The Weenie,” “The Weasel” or “The Idiot.” I was an “idiot” last year and signed up for the same this year.

Then there was Burma Road. As anyone who has attempted to ride it knows, this is the steepest road on the island if not the planet. Right before the climbing starts, the P2P organizers had a sign posted, “This is where it gets ugly.” Another sign on parking lot hill reads, “Welcome to the wall.” You can’t help but smile through gritted teeth.

The P2P even had Jim Marsh from the Chamber of Commerce as its own “Red Devil” to inspire riders up the hills. The real Red Devil is a German spectator named Didi Senft who for the last 20 years has dressed in a devil’s costume and has famously jumped and yelled alongside the most elite cyclists in the world. I have been to a lot of organized bike rides and have never seen a homegrown Red Devil. It was the perfect surprise after biking up Burma Road.

I was one of the last riders to leave Jensen’s Point, which worried me because I knew I would need all the time I could get to complete the course. About five and a half hours in, I realized I was in trouble when I kept seeing the same guy in a red truck behind me. He was picking up the P2P signage! He told me the people in the checkpoint up ahead were just waiting for me before they could go home. After a very short internal argument, I decided to be magnanimous and have them go home. I would, with great reluctance, ride straight to the picnic and start drinking beer.

And what a sumptuous picnic it was, with great local food, wonderful support from the community, including bike repair, massage and stretching stations. Local businesses were even offering discounts to P2P participants, but what really makes this event one to remember is the tireless work of the volunteers. When it became clear to me I wasn’t going to reach my goal, I was feeling pretty glum, yet at each checkpoint I was greeted by a friendly face and good dose of encouragement. So for all the P2P volunteers, you have my sincere appreciation. I hope to see you again next year.

— Chris Austin works at The Beachcomber and is also an author.