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The Upper Market Stairway Walks Trail Is a Sumptuous Love Letter to San Francisco Scenery – thebolditalic

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Matt Charnock
6 days ago·7 min read
One of the joys of hiking the San Francisco Crosstown Trail — an almost 17-mile passageway that weaves through the city, beginning at Candlestick Point and ending at Lands End — is being able to sponge up SF’s numerous superb viewsheds. But again: that path is more than twice as long as the Bay to Breakers race course. From past experience, it takes close to seven hours to complete the trail at a brisk walking pace… sans any water breaks or scenic pauses.
Alas, tackling the SF Crosstown Trail is a commitment I’d wager not too many of us are eager to adopt on a consistent basis. I know I’m not. But the thought of introducing a five-mile hike (that serves up several of the same panoramas) into my regular, pandemic-born walking routine seems more realistic.
As I recently discovered, hiking the Upper Market Stairway Walks trail fits that above-mentioned descriptor to a capital T.
At the base of Corona Heights Park, I was confronted with what would later become the first of over twenty individual stairways along the passageway. Unlike San Francisco’s more ostensibly lavish staircases, the ones which make up the Upper Market Stairway Walks trail are unapologetically utilitarian. They exist as a logistical means to an end; a collection of steps solely designed to help hikers get to and from urban summits. This first one — a staircase dusted with a thin layer of red clay — led me to and above the Randall Museum.
I often forget how impressive San Francisco is, especially when viewed from a few hundred feet above sea level. Most of my days are spent tapping away at a keyboard inside my poorly lit Tendernob studio. My apartment faces a concrete pillar; the occasional wild parrot will grace me with its sentient presence, squawking as if to taunt me with the tangible splendor that exists outside of my Google Drive.
Perched 520 feet above sea level, a view of downtown San Francisco backdropped by an aqua-blue sky, it struck me that I should heed that avian teasing more often. Fortunately for me: the Upper Market Stairway Walks trail would put me in the way of three other SF peaks — those found on Mount Olympus, Tank Hill, and Kite Hill — over the next five miles.
The short jaunt from Corona Heights Park to Mount Olympus is sprinkled with gentle delights. I passed the park’s namesake dog run, which that day saw two corgis waddling to and from their owner; I had the chance to visit the Lower Terrace Greenspace, one of San Francisco’s best-kept secret gardens; I ran into an old acquaintance who noted my taste in running sandals hadn’t changed since we met about two years ago — basically naked at 2019’s Folsom Street Fair.
Mount Olympus, aside from giving off big bonsai tree energy, appears precariously tucked away in Corona Heights. Sandwiched among million-dollar condos, the hill — once considered the geographical heart of SF and the former home of the massive statue titled “Triumph of Light,” from 1887 to the late 1950s — offers a stark juxtaposition between new and old San Francisco. Although the picturesque views are now obstructed by tall buildings, it’s still a magnificent place to find yourself on a weekday afternoon. And unlike Twin Peaks: You won’t have to fret about people, quite literally, getting in the way of your momentary contentment.
Tucked away off Upper Terrace, I found the Monument Way Stairs. It’s, admittedly, a dilapidated (but structural sound) concrete staircase that’s shouldered by greenery. Taking it down led me to 17th Street, allowing me to take Clayton Street down to where it merges with Twin Peaks Boulevard — placing me at the base of Tank Hill.
Trudging up Tank Hill — which, fun fact, got its name for housing a water tower from the late 1800s to 1957 — yields breathtaking panoramas of San Francisco, maybe even more so than those seen atop Corona Heights Park. Depending on the time of day, Karla The Fog will make an appearance to the northwest, blanketing the Golden Gate Bridge in her misty haze. But because of the climate crisis, her atmospheric film continues to thin, year after year. To the northeast, the Bay Bridge and Oakland, as well as parts of Berkeley, sneak into the frame.
But these sweeping views of the Bay Area were almost obscured by a developer in 1977, who wanted to build a 20 unit apartment complex on top of this unique slice of San Francisco. Had Tank Hill not later been bought by the City shortly after and designated as a park, there’s a good chance that these otherwise rocky outcrops would’ve been leveled to make way for condominiums.
Getting myself down again to Twin Peaks Boulevard, the city appeared to soften before my own line of sight. Living in the TenderNob, my impression of San Francisco is one populated by siren sounds, disgorging City-operated trash cans, and sidewalks that may or may not smell of stale urine. But in front of my eyes, there was a genuine stillness present, though a calm still soundtracked by the familiar tone of combustion engines revving to climb a steep grade. SF’s cityscape at this exact moment was refreshing in its mundaneness.
It was also during this pause that I, too, was appreciative that I had the AllTrails app to guide me through the Upper Market Stairways Walk trail. Without it, I might have very well missed what is now one of my favorite stairways in San Francisco: The Pemberton Steps.
Comprising 194 individual steps that span over three separate staircases, the entire footpath is enveloped in hanging greenery. The steps toward the bottom are mossy and cobbled; the gardens there are also better tended and more elaborate than those that shoulder the start of the steps. As someone who cuts their incisors writing about San Francisco’s lesser-known hiking paths, it was a treat to learn that uncovered gems like this still exist for my individual discovery.
As with most urban SF hikes — the Crosstown Trail being no exception to the following reality — it was inevitable that I’d find a long, less exciting stretch of the Upper Market Stairway Walks trail that had no distinct charm. The next two miles proved exceedingly normal as I marched up and down, to and from one sidewalk to the next. However, coming up Douglas Street, I noticed the cafe window at Neighbor’s Corner was mere feet to my right.
Mind you: I’m not one for serendipity. But having earlier pondered about how nice it would’ve been to consume an espresso sometime on this hike, there was some level of kismet at play when I drank that purchased espresso. Perhaps this was manifestation at work. Either way, the jolt my endocrine system craved was satiated.
Walking toward Kite Hill, which would be the last notable ascent on the trail, I made my way through the Seward Mini Park. One local — a longtime resident of the neighborhood, whose flouncy gray hair exuded both glamor and wisdom — who I came across reading on a nearby bench told me she comes to the park most weekday afternoons for respite. She and others who call the area home tend to it regularly — “it’s our token of affection to the city and our community.” The smattering of vibrant flowers, each plant carefully nested in an individual pot, exudes that sentimentality.
Kit Hill, however, exists as an antithetical to Seward Mini Park. Its terra firma is mostly a sprawl of sand and dirt and dust, juxtaposed by leaves and trees and flowers surrounding its peak. Unlike the aforementioned mini-park, there is no tall, shrouding foliage that offers relief from the punishing sun. Shade, however, is traded for moments of picture-worthy pause that allow you to view much of downtown San Francisco. Some of the Castro’s Edwardian architecture can be seen cresting in the distance as if to remind onlookers of the city’s moniker as the gay capital of the world.
Barring a brief glance at a community garden off Market Street — one that was incredibly thick with agave plants and other succulents — the trek from Kite Hill back to Corona Heights Park was, above all else, a familiar communion with San Francisco.
I knew I had about a mile left on the hike at this point. I knew I wasn’t going to have the chance to walk the Upper Market Stairway Walks trail in the glory of the midday sun for some time. I knew, especially having just entered a new decade of my life, that all things (good and bad, ambivalent and otherwise) are fleeting. I knew all of this.
Catching one last look over the city on a bench outside the Flint Street Tennis courts, an immense wave of gratitude washed over me. How this born-and-raised Texan managed to find himself in San Francisco still endures as a pinch-me kind of concept. But I guess you could ostensibly deduce that did, in fact, get here… one step at a time.
Find more information on specific locations and access points to the Upper Market Stairway Walks trail on AllTrails.com
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SF transplant, coffee shop frequent; tiny living enthusiast. iPhone hasn’t been off silent mode in nine or so years. Editor of The Bold Italic.

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