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San Francisco: The city of pioneers

For all its shiny Silicon Valley gloss, the Californian powerhouse of San Francisco is still pioneer country — an undulating urban frontier ruled by extremes

By Sarah Barrell
Published 8 Apr 2019, 23:42 BST, Updated 15 Jul 2021, 15:13 BST
Soaking up the view from Tank Hill.

Soaking up the view from Tank Hill.

Photograph by Kris Davidson

Bay, city, mist-backed bridge… Twin Peaks' panorama is perfection, albeit fairly hard won, preceded by a lung-busting hike up from the Castro just as the morning's sun starts to burn off the fog and fry the hillsides. The climb up San Francisco's second-tallest peak follows a trail where successive hairpin bends open out to reveal a string of excuses to stop, breathe, and take in The View: ocean, skyscrapers, harum-scarum switchback streets. Then it's off again, following the sure-footed lead of Val Hendrickson, a guide at Urban Hiker San Francisco.

This local outfit's mission: to make an aerobically challenging playground out of the peaks, woods and stairways that populate patches of San Francisco's undulating urban map, uncovering historical titbits en route. It's steep. At points, I'm forced to grab handfuls of scrub — which rejoice in such Wild West names as lizard tail and coyote brush. At the top, we stop for a couple of obligatory summit photos and a breather, then I nod to Val and we're off again, scrambling over the guardrail onto Twin Peaks Boulevard — named for the pair of adjacent hills it traverses — jaywalking swiftly across then dropping into woods flanking a fenced-off reservoir.

They might recall the David Lynch TV series but the peaks aren't related in any way to his surreal creation. "The name derives from one given by Spanish settlers," says Val. "Los Pechos de la Choca ('The Breasts of the Maiden')." We leave the hallowed mounds to round the reservoir and climb towards Sutro Tower. The antenna-topped peak — at 1,811ft, the city's highest point — provided hilly San Francisco with its first decent TV reception back in the '70s, before becoming an icon for kitsch-cool T-shirts. We tramp through Mount Sutro Forest — an old eucalyptus wood on its last legs. It's a pungent, shady retreat that rolls down towards Haight-Ashbury.

"The trees came with Australian Gold Rush settlers," Val explains. "They were valuable windbreaks on farms. This was all grazing land back then." It's wet underfoot from fog drip and, further along, a spring seeping out of the ground. "It's hard to imagine people would've once trekked all the way up here with buckets and carts to fill with water," says Val.

In many ways, the story of how the West was won is not one of gold but of water. "Franciscan friars came here for the water source," says Val of the Spanish order that gave the city its name in 1776. It's a source that's since struggled to meet the demand from San Francisco's ever-expanding population. I note the reservoir we just passed. "That's mostly for the Fire Department," says Val. "After the 1906 earthquake and fire that followed, the city realised it needed huge reserves of water to stay safe. People literally ran for the hills to survive back then."

Today, most of San Francisco's water is pumped in from Yosemite, 200 miles away. With droughts and wildfires a regular plague, locals are resigned to a water shortage one day crippling California. It's not a case of 'if' but 'when', they'll tell you — the same phrase they use when discussing the next big earthquake.

Between the woods and the peaks, San Francisco's roads run at impossible inclines — the grand, Gold Rush-funded mansions and townhouses seemingly oblivious to their precipitous settings. At the corner of Douglass Street and Caselli Avenue — where the two streets plunge into what was once known as Upper Eureka Valley — we find Nobby's Folly, a hulking, white-turreted construction dating from the Gilded Age of the late 19th century. "Alfred 'Nobby' Clarke was an Irishman who didn't do so well in the Gold Rush, so he joined the police," smiles Val. "He was also a loan shark with missing knuckles who apparently used to scrap in the street with his competitors — notably his neighbour Behrend Joost, who ran the city's rival water company." The source of their conflict was the spring Joost used, which flowed from his own mansion down through Nobby's, riling the latter to such an extent he set up his own water company, so beginning the tit-for-tat 'water wars', which ended up with both businesses suffering. 

Water: the rags-to-riches resource that saw both men reduced to fist fights and funded 'folly' mansions too big for their respective wives to countenance living in. "Nobby's is now divided into about 15 apartments," says Val. "You can rent the gardener's shed — literally a shack — for about $2,000 per month, I believe. I took a tour of the city when I first arrived here from the East Coast and the guide said San Francisco was founded by thieves, liars and scoundrels. I thought that was a bit harsh, but she was right."

To allow easier access to his mansion, Joost and his two brothers installed the city's first electric streetcar in 1892, nearly two decades after the world's first cable-car was invented in San Francisco to conquer the impossibly hilly grid plan.

Peaks & troughs
Where streetcars and cable-cars can't climb, San Francisco has stairways — hundreds of them, many officially classed as streets, and named accordingly — some giving access to houses, many flanked by glorious patches of flora; pretty much all set in narrow gullies offering sudden glimpses of the city below. Just off a cartoon-steep stairway — suitably named Acme Alley — lies Corwin Community Garden, where I meet Bill and Kathy, custodians of a heroically hilly plot planted with Technicolor lupines, spiky succulents and shrubby perennials. "We're on the north face of the biggest mountain in the city," says Bill, a self-confessed recluse who spends his spare time watching reruns of the UK's Chelsea Flower Show. "I hate wind," he says with a shrug, gesturing at his breeze-ruffled flora. "And it's all clay soil," adds Kathy, completing the against-all-odds picture.

I leave these two taming their precarious patch of Wild West and walk on to Seward Mini Park, a kids' play area built in 1973 on a plot saved from the developers by activist parents. Created by a 14-year-old girl, who won a competition to design the park, it centres around a polished cement slide that runs the entire of the hillside at a breakneck gradient.

A hammering, crashing commotion soundtracks our walk (houses being torn down to be rebuilt). "There are no real preservation rules here," says Val. He explains you have to be ready to fight tooth and nail to keep the developers' wrecking balls at bay here in San Francisco — with everything from gardens to playgrounds and historic buildings up for grabs. It's always been thus. In the 1860 inaugural edition of San Francisco's Overland Monthly magazine, the 'new' architecture was condemned as 'cheap and tawdry' — a snooty condemnation of the florid Victorian homes mushrooming across a city enriched by miners' gold and largely insulated from the costs of the Civil War way out East. It's these hilltop houses — and successive incarnations built on their footprints — that are now being snapped up by the dotcom millionaires currently charged with making San Francisco a place of tawdry gentrification. We pass a Craigslist founder's mansion here, a Zuckerberg house there, and the conversation inevitably turns to data — the modern resource being scrapped over. "I wonder, will future generations be agog at what we gave away for free?" says Val of today's digital identity issues.

I note the irony of my latest app find, a digital poop map of San Francisco. Faced with a fourfold rise in complaints about human waste on city streets in the past 10 years, software engineer Jenn Wong created Human Wasteland, highlighting the plight of the homeless who — in the face of wildly escalating property prices, the mayor's mass evictions from inner-city encampments, and shiny new-era restaurants and bars making restrooms patrons-only — literally have nowhere to go.

While I'm in town, there are reports of Apple and Google staff buses bound for Silicon Valley being rerouted. The aim: to avoid violent clashes with protesters in the city who see the huge influx of tech money as 'toxic techsploitation', inflating house prices and making a chasm of the income gap. San Francisco — America's most expensive urban area to live in — has always been a hothouse city; a place where Gold Rush money — and its modern equivalents — have forced both rapid growth and gross inequality.

With fast growth comes fast living. A city built by gold diggers, gamblers and gluttons for the good life, San Francisco's is a bohemian blueprint. We walk down into the Castro, the mid-morning breeze fragrant with wafts of pot. Yerba Buena, the original Mexican name for the city, means 'good herb', recalling the mint that used to perfume its hillsides. Today, it seems particularly apt, since California recently legalised marijuana. "Have things changed much since the ruling?" I ask Val. "Nah, I don't see much difference in behaviour," he shrugs. "Stoners have always been here."

San Francisco Pride weekend is imminent and Castro is flying its colours. Shop owners deck their displays in rainbow flags, ribbons and balloons; from muscle outfits to butt plugs, things are looking festive. I spot the words 'keep clear' painted on several shop doorsteps and step gingerly around them. "It's to keep people moving," says Val. "Until the '90s, Pride was held in the Castro. It was chaos. These narrow Victorian streets aren't made for crowds. The parade is mainly focused on Downtown now, but the Castro is still where it starts and ends — although there aren't any clubs or venues for shows here," Val adds. "Not like, say, New York's Village." Then he remembers that the ornate old Castro Theatre usually puts on a Pride-related double bill — its Wurlitzer pipe organist still playing on a platform that rises up from the floor during intermissions, just as it's done since the theatre's 1920s heyday.

There's a calm-before-the-storm feeling in the Castro this morning. "Lots of the older generation leave the city for the weekend," says Val. "These days, Pride has such a young demographic, and there's tension between them and the older crowd, who feel they fought for civil rights now being taken for granted; that Pride is just an excuse for another party." In Twin Peaks Tavern — said to be the first openly gay bar in America — I pass a couple of old timers nattering over a glass of white; they're seated at the out-and-proud bay windows; a brazen act in 1935 when the tavern opened.

Fusion flavours
I bid goodbye to Val, and head around the corner to Kitchen Story, where brunch comes with a party punch. 'Eye-opener' cocktails include mimosas, Millionaire's Mary (with bacon), and the Castro Michelada (Thai beer with Bloody Mary spices). The Cali-Asian fusion extends to the food menu, and the lively crowd: Hispanic boys in rainbow feather boas, transgender and lesbian couples, and pan-Asian groups with kids.

I walk off my Belly Rancheros (slow-braised Kurobuta pork belly, avocado, rocket, kimchi pico de gallo, guacamole, corn tortilla) along Mission Street, which traces the old Camino Real — a road that once linked California's 18th-century Spanish missions. Apart from the white adobe church Misión San Francisco di Asís — San Francisco's oldest intact building, dating back to 1776 — there's little trace of this pioneer pathway.

It takes me 20 minutes to walk from a place with a key role in San Francisco's origins to one of it's latest happening hoods. Bordering Japantown, the Fillmore District is where I find the recently opened Merchant Roots, an artisan market-cum-cafe. The shelves are stacked with pasta, the walls adorned with locally woven art, and salads and Californian wines are served at its communal table.

It's the newest opening on Fillmore's fastest-developing stretch — also home to Fat Angel (beer and comfort food) and new, self-styled 'elevated' Asian eatery, Avery. Opposite, the long-abandoned Fillmore Heritage Center is slated for imminent revival as a theatre and event space. A few blocks away, long-standing landmark Miyako Old Fashion Ice Cream survives; I stop to select a couple of its 100-plus flavours. Meanwhile, the Boba Guys bubble tea parlour nearby seems to be catering to Fillmore's entire — sipping and selfie-ing — 18-30 demographic.

Despite its handy location, between leafy Golden Gate and Presido Parks, Downtown and Fisherman's Wharf waterfront, so far Fillmore has few hotels. Mine, the Kimpton Buchanan Hotel, is all dark, moody paint and bright city views. I can't find a suitcase stand but the wardrobe has a yoga mat and tie-dye robe — a nod to the city's hippy heritage.

Just to the north, in Fillmore's already-gentrified core, I find more tie-dye, as well as combat jackets, acid-hued platforms and more at charity shop Crossroads. "We've been here 25 years," says the shop assistant. "I think we're the only original business left." It's still doing a roaring trade between new neighbours that include slick Italian SPQR (where I dine on salumi) and perfume store Le Labo (where I sniff a fragrance inspired by San Francisco: Limette 37 — apparently the city smells of bergamot and jasmine with a little tonka bean thrown in).

Heading south east to SoMa (Downtown's fastest-changing hood), I make a beeline for August 1 Five, a restaurant serving modern Indian — the city's ethnic cuisine de jour. Here, a cardamom-scented bison keema (ground bison, caramelised onion, bacon, quail egg) and a vivid green Jaipur Emerald cocktail (tequila blanco, coriander, green chilli and toasted coconut) are sensory standouts, after which I could do with a walk. Sadly I'm a few weeks too early to enjoy the elevated delights of SoMa's Salesforce Park. San Francisco's 20-years-in-the-making answer to New York's High Line isn't yet ready for visitors. Shortly after I leave, it opens, then closes again due to cracks in steel support beams — prompting speculation the problem might be related to the ongoing crisis at neighbouring Millennium Tower, the city's tallest residential building. Opened in 2009, the 58-storey Downtown skyscraper is slowly sinking and developing a Tower of Pisa-like tilt (a worry, given the city's earthquake zone setting).

My final stop is at the latest outpost of glass-ceiling-busting chef Dominique Crenn — the only woman in America to head up a two Michelin-star restaurant. Atelier Crenn's new neighbour, Bar Crenn, recalls a 1920s Parisian salon. "Lately, they're all the same," says Crenn of the city's current crop of slick designer restaurants. "I was missing romanticism and history. When I arrived here from France six years ago, I felt such freedom of creativity," she says. "There were no barriers; I could do anything I wanted. If I'd tried Atelier Crenn in New York it wouldn't have worked." Crenn bemoans how tech money is changing the 'essence' of San Francisco — an essence she believes has a foundation in solid, supportive community. "It's this that allows people, no matter where they come from, to enable their voice, to find their creativity," she says. "And this is what San Francisco is about."


Getting there & around
British Airways, United Airlines and Virgin Atlantic have direct flights from the UK to San Francisco International Airport. Norwegian flies from Gatwick to Oakland International (similar distance from the city). 

Average flight time: 11h.

More info
Urban Trails San Francisco, by Alexandra Kenin (Urban Hiker founder). RRP: $16.95 (£12). (Mountaineers Books)

Where to stay
The Kimpton Buchanan

How to do it
America As You Like It offers a three-night package travelling to San Francisco from £1,190 per person, including return flights with Virgin Atlantic, and three nights accommodation at the Kimpton Buchanan Hotel, room only. Price is based on two adults sharing a Standard King room. 

Follow @travelbarrell

Published in the December 2018 issue of National Geographic Traveller (UK)

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