Last weekend, as I slogged up a dirt path in Glen Canyon Park, framed by granite boulders and impenetrable brush, I wondered for the first time whether I could even finish the Crosstown Trail.
Two close friends and I had already traversed seven miles of earth and asphalt, and were nowhere near the halfway mark. Once upon a time, I embraced the thrills of hiking insane distances to the summits of 10,000-foot peaks. But now, after weeks of sitting on a couch to rewatch The Sopranos, I had to face my penance for impulsively agreeing to a 17-mile trek across San Francisco.
The trail serves as a backdrop for a lesson on SF history and diversity, guiding you through parts of town that you may have passed by over the years. It unveils the well-hidden green spaces that dot every corner in town. And it shows the full breadth of city life, from the working-class shops of Visitacion Valley to the eye-watering capitalist excesses of Seacliff, where 17-year-olds park their Range Rovers in the driveways of $7 million homes.
Yes, the length of the trail is daunting, but it is doable for a reasonably fit person. Some people even split it into two parts over two days, but for me, tackling the entire seven-hour journey left a memorable, if painful, reminder that SF might be the most interesting city in the world.
We emerged from greenery onto busy Portola Drive and began the second push uphill, toward Twin Peaks. As we approached the highest point of the trail, I gazed up and saw a finger of sunlight, spotlighting the trident-like arms of Sutro Tower.
The city sprawled ahead of us. We could almost see our destination: Lands End. I tightened the laces on my boots, as if it would help with the next 10 miles.
The Crosstown Trail debuted on June 1, 2019, after years of planning and discussion by volunteers and the nonprofit San Francisco Parks Alliance. It weaves across the city from Candlestick Park to Land’s End, connecting the bay to the sea with a patchwork of sidewalks, parks, and hiking trails.
Five years later, the journey remains wondrous and challenging, offering intrepid walkers an all-day experience unlike any other. Much of the credit goes to the inherent geography of SF — a captivating little dollhouse of a city compared to other urban sprawls.
Part I: Settling in
It’s been nearly a decade since Candlestick Park, former home of the Giants and 49ers, was demolished and morphed into a recreation area along the coast. It’s a fitting place to begin the Crosstown Trail early in the morning, when all is quiet save for bellowing seagulls, the hiss of fishing reels, and some happy chatter from families lighting charcoal grills.
A soft fog on the water made the bay look endless, with water and sky blending into nothingness at the horizon. But after traversing the loop around Sunrise Point Pier, the trail took a bizarre vibe shift, running through a collection of office buildings just alongside the 101.
We returned to beauty when we hit the Visitacion Valley Greenway, a loose collection of gardens and community parks linked by an uphill path. I couldn’t help but marvel at the flora, so carefully tended by neighbors. The monarch butterflies and hummingbirds were out in force, too.
Next came John McLaren Park, the first proper challenge of the hike. We gained about 400 feet in elevation while trudging up the hillside, painted in shades of mahogany and black by a brush fire sparked by fireworks in July. At the peak, I was greeted by some middle-aged Chinese aunties, stretching in meditative fashion while soaking in the views.
Part II: Climb, and climb again
We hoped to get a break after that first little climb, but tough luck: The next three miles comprised a steady climb to the highest point of the trail. Thankfully, Glen Canyon Park is gorgeous, resembling a proper mountain hike more than any other section of the trail. What was really surprising, however, was the muddy path that winds around Laguna Honda Hospital. It was off-limits to the public until 2019, and still feels like a portal into a random forest. (Also, why was it so wet when everything else was dry?)
We walked up the suburban streets of Forest Hill and past Rocky Outcrop Park on 14th Avenue. We were greeted by a well-fed coyote, which trotted along the blacktop before slipping away into a crack between two boulders. Up next was one of the city’s most iconic photo ops, the 16th Avenue Tiled Steps. Beautiful as they were, my attention now went to my hamstrings, which throbbed with every step I took down that gigantic staircase.
Part III: The “easy” part (yeah, right)
Once we were down in the avenues of the Sunset neighborhood, I assumed we were in the clear, even if we had eight more miles of flat ground to go. We celebrated with a leisurely lunch at Saigon BBQ, complete with cold beers. The three of us even bragged about how we were ahead of schedule.
When we first got back on the trail, that big lunch felt earned. I damn near ambled through Golden Gate Park and up Park Presidio Boulevard, but by the time we hit mile 13, my body began protesting the demands of the journey. My calves rippled with pins and needles. My lower back ached. The arch of my left foot began to cramp in short spurts. (Clearly, the power of rice noodles had worn off.)
Listen, the Presidio is picturesque. The cute “boardwalk” path that led us to China Beach, as well as the obscenely desirable mansions of Seacliff, were genuine aesthetic highlights of the trail. But dear God, I could barely register that we were standing outside of Robin Williams’ house. My body had entered survival mode.
There is a great irony in finishing this journey in Lands End, one of the most beautiful parts of San Francisco, only to stare at the ground, wincing with each step and muttering curses as happy dog-walkers wonder what the hell your deal is. Each (admittedly tiny) uphill segment here felt like a monstrous insult to my being. When we reached the end of the trail by the Sutro Baths, I practically fell to my knees in the parking lot.
Deepest gratitude to our Uber driver, who took three stinking, dirt-stained travelers into his gleaming BMW with nary a comment.
We sat in silence, too exhausted to talk. Then, something beautiful happened: I began to feel the first true swell of accomplishment.
We really had walked across the entire city. And it made me never want to leave.
