Well past dusk with the clock ticking ever closer to 8pm, just before the traffic light turns green I cinch my backpack a hair tighter and clip in. The Saturday night pedestrian revelry is teeming along the San Francisco Embarcadero and given that our first pedal stroke was at the very pre-dawn hour of 5am nearly fifteen hours ago, I’m guessing my reaction time is at least mildly compromised.
This particular Saturday morning is the morning of Milan San Remo, the longest race on the UCI calendar by a sizable margin. The nearly 300 kilometers race stretches from Milan directly south to the Mediterranean coast and then westwards to San Remo. There are three notable climbs covered over the entire race — the Passo del Tuchino is smack in the middle of the route and generally doesn’t factor into the overall result, while the Cipressa and Poggio arrive in the final few minutes of the race and everything hinges on these two peaks. While not a terribly interesting route, the superlative title of longest offers incredible prestige to MSR.
Having now called the Bay area home since only January and having retired just a month prior to that, my immediate circle of friends and the community around me are all one degree removed from cycling. This sport defined the previous decade of my life as I lived overseas and always operated at the beck and call of my team. Camps, races, and an absurd travel schedule dictated virtually every day of the past ten years of my life. Now retired from racing, I have a more astute perspective for the broader spectrum of that word that defined my life, cycling. Racing is one acute facet of cycling that now falls under the “Been there, done that” category, whereas the general world of cycling — social empowerment, youth leagues, cycling to relieve health woes, social stresses, traffic and a laundry list of other benefits — encompasses so much more. Look, racing is cool and all, but riding is purely fun.
There are few things I like more than collecting a group of friends and setting out on some adventure revolving around the bicycle. San Francisco cycling culture is incredibly strong and the three impressive peaks dotted around the city, Mount Tamalpais to the north, Mount Hamilton to the south, and Mount Diablo to the east, each have a distinct profile and subculture in their respectful areas. I’ve raced eight of the ten Tours of California’s as a professional, so these are all mountains I’ve raced up or pulled a peloton across. Linking all three peaks into a single day via bike, however, is such a geographical stretch that it seems impossible.
Enter my friend Nate, a longtime friend from the inGamba cycling family, he orchestrates cycling routes professionally with an atlas-like knowledge of local roads. Better yet, his predilection for full day adventures on bikes is matched by mine and the hodgepodge new network of friends in San Francisco. What immediately seems impossible is suddenly tantalizingly easy. Nate has been juggling this idea for years, so he and I began scheming, vetted a motley crew, and settled on nine people crazy enough to consider it. Every single one replied to our scull and crossbones invitation to the effect of “That sounds ridiculous. Okay, I’m in.”
The route begins in Mill Valley and rides up and down Tam(alpais); it spans across the Golden Gate Bridge, and then along the north edge of San Francisco to the… train station. A seven dollar train ride shuttles you 90 minutes south to San Jose where you’re back on the bike soon climbing up and over Hamilton across a lengthy expanse with Diablo looming in the distance for hours. From there and riding on fumes, it’s onto a nearby train station, a mere three dollar train ticket sends you back into the city, and a relatively short but precarious spin takes you — at dusk and with the clock ticking ever closer to 8pm — through the Embarcadero and back into Mill Valley. All told 276km (171 miles) are pedaled with over 5,500 meters (18,000 feet) climbed. Mind you, that does not include the more than two hours ridden in a train.
Closer inspection reveals some cozy nuances. This is a public train, for example, so hopping on for an hour and a half in kit that’s just been worn to summit a near-one hour climb is certainly a possibility, but the person sitting next to you likely won’t recommend it. 170+ miles is a noteworthy distance for any cyclist so parsing out nutrition, factoring in ever-changing Bay area weather and the changes of clothes, mechanical hiccups, as well as purely for a sense of security makes the addition of a follow car a convenient addition. To stop for three minutes to top up bottles, swap into dry socks, or grab a bite to eat saves more than just the ten minutes of hunting down a gas station or planting a backpack in the woods with fresh clothes — right, provided you have a friend psyched to drive the entire day.
Plus this now involves bikes, trains, and a rover car; multimodal is just cool.
When my 3:30am alarm sounded, I jumped out of bed like a five year old on Christmas. I’ve always loved cycling but for me it’s now fun again. Admittedly it’s not just anyone who will hop on their bike and grind out 175 miles, but divided into three segments, given the unique twist adding public transport, and sharing the journey with a bunch of friends, some old and some new, makes a day like Three Peaks suddenly very tangible for any intrepid cyclist. Besides my retired self, our group of nine contained no one with pro cycling heritage; everyone has normal jobs, a Strava employee included, and eeks in training whenever possible.
Watching Milan San Remo on TV is a long grind with all the action coming in the final moments of a seven hour race. There’s a gargantuan disconnect for a monument like that; they’re there and we’re here, that’s a race few civilians would care to complete. Covering that same distance on your home roads with friends, however, celebrated toasting beers, some very relieved hugs, and high fives at the finish, that’s what makes a ride fun. I’ve ridden and raced thousands upon thousands of days. The Three Peaks ride is a superlative as one of those rides that will forever live in my mind. We’re already buzzing for the next one.