Crosstown Train (part 1)

A field trip to San Francisco's epic new urban trail

Climbing through John McLaren Park

New England is where this newsletter started, but I never said it would remain rooted here exclusively. While hiking with a more localized mindset can open up familiar landscapes in ways that can be surprising (“I didn’t know there was an old weedy trail behind the Price Chopper”) there’s something to be said for immersing yourself in a different locality—whether it’s an unfamiliar mountain range or a major city that you’ve never really poked around by foot, beyond the usual tourist haunts.

So this week, I’m reporting to you from San Francisco’s Crosstown Trail.

This 17 mile trail across the city’s under-sung green spaces and economically stratified neighborhoods is the ultimate urban hike—replicating the experience of hiking in the backcountry in the middle of a city. How does the Crosstown Trail pull this off? By taking you through a dizzying range of curious environments. Briny coves, primeval woodlands, sun-baked hillsides, hidden community gardens and footpaths, and gusty cliffs are just a handful of the places that I experienced while hiking on the Crosstown Trail. To demonstrate the power of this hike, I’m going to show you what I saw, in two newsletter installments.

But first, a little history. The Crosstown Trail was created by San Francisco residents who felt that an epic trans-city trail might be a possible thanks to the proximity of the city’s ample green spaces. By “simply” connecting the green spaces through carefully selected street walks, restored paths, and some newly built trail segments, one could hike from Candlestick Point to Land’s End. While the trail concept was sanctioned by the city government, the mapping and connecting was performed by a hearty coalition of volunteers. (In this way, it’s actually pretty similar to how the Cohos Trail of New Hampshire was greenlit by the state but built by the volunteers who dreamed it up.)

The Crosstown Trail opened in 2019 and since then, a handful of stories about the trail have propagated this idea that the trail could be something of a tonic for the horrifying inequality which has played out on the streets of SF. (More than 8,000 people here are currently unhoused.) While this sounded a bit trite when I first read about it—upzoning and building dense affordable housing would go a lot further—I was still moved by the concept of an epic trail that takes you from a relative working class neighborhood like Visitacion Valley to the seaside mansions at Land’s End and the Presidio. A long trail might not “fix” San Francisco but it could at least chip away at the privacy of the rich and take visitors into storied communities that most folks probably aren’t aware of.

Old water tanks in the Laguna Honda eucalyptus woods

With the help of maps and written directions from the Crosstown Trail website (these maps highlight transit stations and bathroom facilities) I planned to hike the trail over two days, using the city’s public transit network to access trailheads. You could crush the whole hike in one long day, but as we’ve discussed in prior newsletters, one of the perks of urban hiking is being able to detour into coffee shops, family restaurants, and libidinous-looking bars. In the mountains, your option for a trailside reprieve is often just a boulder or a log. So I didn’t want to rush my Crosstown journey. I wanted long mileage days with enough room for following scents and chewing on some scenery.

Thankfully, the Crosstown Trail is divided into five segments, so a “section hike” of the trail is easy to plan. I printed the maps, tossed some protein bars in my daypack, and went to bed the night before my hike in a budget hotel on Fourth Street (appropriately enough, the joint was called The Mosser.) I was so excited that I woke up at 4am.

SECTION 1 - CANDLESTICK POINT TO GLEN PARK

The traditional way to hike the Crosstown Trail is to start from its southern terminus on the bay and finish at the Pacific overlook at the trail’s northern end. From the city center, I caught two early morning buses—the 8 and the 29—to reach a quiet, foggy expressway that leads to Candlestick Point State Recreation Area. Candlestick Point is often cited as the former location of the city’s Major League Baseball stadium, but it’s also one of the city’s most marginalized neighborhoods, where the working poor have been relegated after decades of redlining and soaring housing prices. Bayview, the larger community to which Candlestick Point belongs, was once a historically Black neighborhood of San Francisco, but many residents have now been displaced.

The recreation area is used by fishermen who cast their lines in the lapping surf from the grassy shore and a handful of piers that jut into the water. But I got here so early that my only companions were a flotilla of chattering seagulls that reminded me of the civilian boats at the end of Dunkirk, crossing the English Channel. I saw them just a few minutes after I entered the park by hopping over a concrete barrier (to avoid walking along the sidewalk-less expressway to the main entrance.) Soon, I could also hear the sound of chattering men on fishing boats, somewhere nearby in the fog.

Setting off from Candlestick Point

I expected to find a marker or beacon announcing the start of the Crosstown Trail but there’s not much physical signage along the trail: just a couple stickers affixed to sign posts here and there. This might be intentional. One of the main visionaries behind the trail, Bob Siegel, didn’t sound particularly keen on the idea of the trail blowing up when interviewed by the New York Times back in 2019. The Crosstown Trail is as much a rustic orientation exercise as it is a hike, and I appreciated that. I spent most of the hike with a paper map in one hand and my phone in the other, set to camera mode.

I set off along a little-used coastal path past fragrant marshes and lonely condos that materialized through the morning fog as the trail curved northwest, leaving the ocean behind and climbing into the foothills of Visitacion Valley. The apartments and houses around here are home to many of the city’s Asian and Latinx residents, and one of the most inviting small businesses along this stretch of the trail is Mission Blue, a coffee nook that sells Crosstown Trail apparel and art made by locals. With just shy of three miles under my belt, I rested here with a cortado and a “morning bun” (a churro muffin, basically) and I tried to ignore the nagging ache in my soles, knowing I had six miles of walking to go. The Crosstown Trail is half dirt and half concrete. Shoes with good cushioning are an essential if your feet become tender after hiking on rock surfaces.

The gates of the Visitacion Valley Greenway

Almost immediately after the trail passes by Mission Blue, things get very verdent and scenic in dramatic fashion. The Visitacion Valley Greenway takes you up through a charming greenway of blooming gardens tucked between hillside houses (the final leg of this greenway features some a cool wheelchair-accessible switchback trail.) Then, as the grade intensifies, you suddenly emerges from the residential area and climb even higher into John McLaren Park up an exposed sunny hill. It’s steep enough to get you sweating, but the views of Southern SF are thrilling and the trail soon levels out, venturing into a forest featuring redwoods. Through the towering arbors, looking northward, I could glimpse labyrinthine rows of houses closer to the city center, and some of the other mountain-like hills that I’d be slogging up further along the trail.

While it would be pretty lush if the Crosstown Trail were just green, it wouldn’t be truly representative of San Francisco. The reality of an urban hike is that you’re going to be doing some solid “street walking” between the green. To that effect, the makers of the Crosstown Trail have chosen some interesting manmade areas for directing the trail. After leaving McLaren Park, I entered a residential neighborhood called Excelsior and ambled past street art-festooned buildings to a long fenced-in footbridge over the 280 freeway. A quick push up another hill past a dog park and a longer sunnier stroll amid more upscale houses with roses bushes delivers you to the BART subway station in Glen Park. This was the site of my next trailside meal (a big ass carne asada burrito from La Corneta Taqueria) and it’s also the end of the first Crosstown Trail section.

From here, things escalate.

Crossing the 280 freeway

SECTION 2 - GLEN PARK TO FOREST HILL

San Francisco is full of “places in between” that have been transformed into heavenly greenways and the one near the Glen Park subway station delivers you to the entrance of Glen Park Canyon. The place is something of a shrine to civil disobedience. A small group of women known as the “Gum Tree Girls” stopped a highway from being built in the canyon back in the 1960s and the Crosstown Trail follows a semi-paved path that was named after the activists, entering the scrubby woods in the canyon. From here, the route gets rockier and brushier, seguing to a second hiking trail that was cut by a teacher and his students. Nearby homeowners didn’t want this trail to be built, citing their privacy, and the trailblazers basically told them to fuck off. Nellie Bowles wrote about this in a Crosstown Trail story for the New York Times. I couldn’t help but grin as the trail took me up to the sunny rim of the canyon, past elegant houses on stilts.

Heading deeper into Glen Park Canyon

But Glen Park Canyon was just the salad in a smorgasbord of earthly delights. After a bit of road walking up Panorama Drive to one of the highest points of the trail (with a fittingly panoramic view of the city) I reached the main course of my day—the Laguna Honda forest. I recently wrote about these forgotten woodlands and the relatively new hiking and biking trails here that the SF Urban Riders built themselves. The Crosstown Trail follows their sidewinding paths down through the eucalyptus woods, past the Laguna Honda hospital and into a leafy ravine that used to be a garbage dumping zone. I kept an ear open for the grinding of mountain bikes (the trail here gets pretty narrow and is often flanked with poison oak, which makes diving out of the way of a bike more troublesome) but I scarcely encountered another soul. The green ravine, in particular, felt like something out of The Land Before Time, even as the large hospital grounds rattled and hummed less than a quarter mile away from this serene space.

The ravine in the Laguna Honda woods

It was now 2pm and the array of scenery along the first half of the hike had been so enlivening that my feet were now less sore than they had been earlier in the day (the dirt paths at Laguna Honda and Glen Park Canyon surely helped.) But as I descended a more illuminated hillside toward the Forest Hill light rail station—the Crosstown Trail route visits many convenient public transit stops—I could feel a strain of anticipation for what lay ahead the next day: a long, punishing ascent to higher grounds and then, a meandering pilgrimage to the edge of the land on which San Francisco was built. I reached Forest Hills station having walked 8.5 challenging miles and called it a day. I would take the light rail back to my hotel, get horizontal on the bed for an hour or so, attempt a brief recovery walk to the Lower Haight, and hopefully walk into some half decent tonkotsu ramen with extra BBQ pork. (When in San Francisco, live deliciously.)

The next morning, the hike would go on.

Trailside at Mission Blue