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A ride into the hills

on November 3, 2009

For Bay Area cyclists, November is the cruelest month. Night falls earlier and earlier, and winter winds and rains prompt many of us to place our two-wheeled conveyances into hibernation for the next few months.

November 2009 has been different so far, however. The region’s Indian Summer has lasted more than a month into autumn. Clear skies, 70-degree temperatures, and abundant sunshine have greeted us outside our windows over the last several days. You’d think it was Easter, and not Thanksgiving, that waits just over the horizon. For people who love to ride their bicycles, it’s as though the meteorological judges have issued a stay of continuation from the bench.

My first perceptions of Oakland came not on a bicycle but from a 1981 Oldsmobile Cutlass Cruiser station wagon, with faux wood paneling on the sides. I was 8, and my father and I were coming down from suburban Sacramento to an Oakland A’s game at the Coliseum. The A’s of Ricky Henderson, Dwayne Murphy and Carney Lansford—a few years before the World Series champion Bash Brothers, Mark McGwire and Jose Canseco—took on the Kansas City Royals, who wore their peculiar powder blue road uniforms. Baseball fashion was still working its way through its baroque phase.

On the way to the game, the view of Oakland from rush hour traffic on the Cypress Freeway, which collapsed a few years later in the Loma Prieta Earthquake, was one of old Victorian houses and long avenues splashed in sunshine. The buildings were imposing in their height and number—it would be years before I would see New York—and “Jack London Square” had, to my young ear, connotations of adventures in the Alaskan wild. My family had just moved to California from Michigan, and palm trees seemed to be everywhere. From above, Oakland impressed me as a hive of activity—a place where grownup people conducted their grownup lives.

I moved East as an adult, but then moved back to the Bay Area five years ago with my wife. We live in Berkeley, but my acquaintance with Oakland has grown through my bicycle rides over the last few years. North Oakland has to be one of the best urban areas to ride, with long, flat thoroughfares like Market, Broadway and Telegraph. I’ve wandered in and out of Temescal, Golden Gate and Bushrod, picking up hints of the rhythms in different neighborhoods. Occasionally, I stumble across something I would never seek out, like the Chapel of the Chimes—Oakland’s crematory and columbarium—in Piedmont or the Coffee Mill & Bakery, Oakland’s “oldest coffee shop” on Grand Avenue. Often after work during the summers, I would hop on my bike and head down to Lake Merritt, where Oaklanders comes to walk, cycle and jog away the early evening hours.

There’s always been one Oakland bike ride, however, that’s eluded me. The ride into the hills behind Rockridge, with their achingly beautiful views of Oakland and San Francisco below, has been the White Whale of my Oakland cycling horizon. But with November days that feel more like summer than fall, the hills finally called my name this morning. And, like those first impressions I gathered of Oakland from the Cypress Freeway, there’s still something about me that longs to see Oakland from above.

"Keeping it wheel" above North Oakland

Keeping it wheel above North Oakland

There’s a reason I’ve never made it to Upper Rockridge on my bicycle before, of course. The incline up Ashby Avenue near the Berkeley-Oakland border is preposterously steep. I nearly had to stop at the Claremont Hotel for triple-bypass surgery and then half-expected to see Sherpas on the last stretch of road leading up to the Caldecott Tunnel above Highway 24.

After a much-deserved rest stop, I finally made it to the summit, crossing over from Berkeley into Oakland near College Preparatory High School. For a few moments, life in Oakland unfolded as though it were a toy, a series of dolls’ houses or an electric train set. Lake Temescal glistened in the early morning light. Traffic moved swiftly across the elevated stretch of Highway 580. And behind a veil of light fog, San Francisco beckoned over the horizon.

Down below, the busy world seemed hushed. At this remove, everything appears serene. Yellow busses carried children to school. Husbands and wives traded kisses before grabbing their coffee and heading off to work. And, for a few minutes at least, I was small once again and Oakland was a place where grownup people went about their grownup lives.


  1. Andy K on November 4, 2009 at 10:37 am

    So, did you make it all the way up to Grizzly Peak Dr.? The climb up Tunnel Rd. is doable. Only one short section of steep road. Well worth the effort.

  2. John on November 4, 2009 at 12:44 pm

    Hi Andy,

    Have yet to make it to Grizzly Peak Dr. Maybe this spring!


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