Exploring San Francisco’s ritzy, raffish heart has never been more interesting

Related: Market Street’s best bets


Market Street is San Francisco’s grand boulevard. It links a briefcase-toting lawyer at Justin Herman Plaza to tourists waiting for the cable car at Powell Street to a resident walking his terrier under the sycamores in the Castro District. Angling 4 1/2 miles across town from the Ferry Building to the slopes of Twin Peaks, Market is the one irreplaceable thread in the city’s urban fabric.

Strangely, it’s also taken for granted. Maybe Market Street is too long, too diverse, too obvious. Drivers searching for a left-turn lane curse it; pedestrians used to avoid it.

But over the last few years, Market has come into its own. Chic restaurants and hotels line its lower blocks; the Castro, at its upper end, remains the capital of kitsch and cool. Historic streetcars roll its length, and the Ferry Building is readying itself for a grand reopening. In short, Market Street has never looked better.

“On Market, you feel the history of the city,” says San Francisco architect Earl Wilson. And he’s right. For all its present-day bustle, Market is redolent of the past. Its pavement ties a journalist strolling its sidewalks in the 21st century to 1940s office workers in fedoras at the Flood Building to waterfront gamblers of the 1840s. It’s where San Franciscans have always come to protest and parade.

“It’s our celebratory street,” says the Market Street Association’s executive director, Carolyn Diamond.

An afternoon, a day, or a weekend spent exploring Market yields the fullest possible portrait of San Francisco. The street offers a 100-year tour of Western architecture and some of the city’s best shopping and dining. Travel Market’s length and you’ll get a slice of the city, rich as a layer cake.

The path of gold

Start your Market Street day at the street’s northeastern end―specifically, at the Ferry Building, the classical structure with a dramatic white clock tower that has been a city symbol for nearly 100 years. Take a look down the long, grand stretch of pavement ahead of you. The 120-foot-wide street has been called everything from the “Path of Gold,” for the prospecting hopefuls that rushed in from the bay, to the “Pathway to Propinquity,” for the streetwalkers who showed up a short time later.

From here, you can march into San Francisco history. Building names announce players of the city’s past: Southern Pacific, one of the builders of the transcontinental railroad, which brought so many settlers here; Matson, the shipping company that connected San Franciscans to Hawaii and other Pacific destinations; Pacific Gas and Electric, the power empire that fueled the West.

When it was laid out by Jasper O’Farrell in 1847, Market was surrounded by 80-foot sand dunes―soon leveled and used to fill in the bay―but nonetheless was conceived as the main route from the docks to the city’s original center near Mission Dolores. The diagonal route created a seam that zips together the city’s two skewed grids, one tilted 45 degrees from the other. In 1860, Market’s first steam train rolled down its tracks.

The post-earthquake fires of 1906 destroyed most of San Francisco’s Victorian buildings, but the city was rebuilt amazingly fast. By August 1907, 6,000 buildings had been replaced―and 3,000 more were underway.

In the 1930s, two new bridges into the city meant that fewer people were using the Ferry Building, and, when combined with the effects of the Depression, Market went into decline. It was an indication of the street’s fading prominence when designers of the 1959 Crown Zellerbach Building turned their back on Market, locating the main entrance on Bush Street.

Then, construction of a tunnel for Bay Area Rapid Transit (BART) and San Francisco’s Muni Metro virtually shut down the street. With Muni’s light rail vehicles now running beneath Market for much of its length, some city officials wanted to rip out the streetcar tracks on its surface.


A street both homey and chic

The middle portion of Market looks to its past as better days. The section between Fifth and Seventh Streets used to be a lively theater row, but it has since declined into a collection of pawn shops and adult theaters. “It’s ironic that when they put in BART, the Market Street Beautification Project was launched. And that’s what really began the skid of mid-Market,” says Gray Brechin, urban geographer at UC Berkeley and author of Imperial San Francisco: Urban Power, Earthly Ruin. Just west of Van Ness Avenue, auto showrooms give way to a two-block district of design studios and antiques stores. Nearby, Zuni Café is a quintessential California restaurant—like Market Street, it blends homey and chic in its decor and food. (Other Market Street standouts range from glossy One Market Restaurant, down by the bay, to the 70-year-old It’s Tops Coffee Shop, with tabletop jukeboxes and dinner available until 3 A.M.)


The new gay, lesbian, bisexual, and transgender community center marks the gateway to Upper Market and the Castro, called Eureka Valley a generation ago. The neighborhood has a cozier feel, in contrast to downtown’s looming architecture. And the district’s revelatory, be-yourself air gives the place spirit. “Even the trees thrive here,” says Brechin.


A sunny morning draws crowds of post-gym tank-top wearers and serious newspaper readers to the woodsy patio of Café Flore. Victorian homes rise up the hills, looking down on the storefronts and sleek restaurants that pack this neighborhood.


Across the street, assassinated city supervisor Harvey Milk and victims of AIDS are honored in a colorful mural, a visual reminder of wounds that run through this community.


“Castro isn’t just a neighborhood, it’s a suburban village,” says Market Street Railway’s Rick Laubscher. “The cable car shaped this place. A village grew up at the end of the line.” At Castro Street, the streetcars loop around Market to change direction and head back toward the Ferry Building.


Living on Market time

Laubscher, whose great-grandparents opened a deli on Market in the 19th century, worked to retain Market’s streetcar tradition when planners wanted to demolish the tracks in the 1970s. “These were tracks that had been there since 1860. And I thought, 120 years of transit tradition is coming to an end?”


Vintage streetcars ran as an experiment in 1983. A permanent line, the F-Market, opened in 1995. The colorful vintage cars—from Hiroshima, Melbourne, New Orleans, and Philadelphia, among other cities—have become a signature of the street.


Now president of the nonprofit Market Street Railway, Laubscher describes the landmark Flood Building on Market at Powell, as “one of the great office buildings of the 20th century.” The stately structure is triangle shaped to fit the odd angles created by Market’s orientation. Nearby, chess tables line the sidewalk’s edge and a dreadlock-wearing duo pounds out rhythms on plastic tubs. Behind them, an orange streetcar from Milan delivers a ponytailed girl laden with shopping bags.


Across the street from the Flood Building, the 20-foot-tall Albert Samuels Clock has four time-telling faces, its inner workings swinging to mark the seconds. “I listen to that old street clock,” Laubscher says, “and think how many entire lives have ticked away in its vicinity. When Dashiell Hammet was writing, he walked under that clock every day.”


Another streetcar, a blue and yellow one that first ran in San Francisco in the 1940s, rattles past. And the clock keeps ticking, in time to the streetcar’s distinctive rumble.

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