Walking San Francisco

There is little disputing that San Francisco got off to a spectacular start. By all accounts, the city was thrown up with the purposeful chaos of a carnival pulling into town in the dark of night. For decades the atmosphere in many parts of town pulsed with a stridently lawless spirit. The area between the main plaza and the wharves managed to distinguish itself as particularly rough and became known as the Barbary Coast.

The name suggested a likeness to the pirate-infested coast of North Africa, where European sailors risked being captured and enslaved on corsair galleys. The district functioned like an angler fish preying upon sin-seeking sailors. For its lure it had block after block of gambling dens, whorehouses, music halls, saloons, and boardinghouses. Serious consequences awaited those who were outsmarted here. The neighborhood was rife with swindlers and shanghaiers. For the unwary miner or shore-leave sailor, the path of least resistance generally led to a knock-out blow in the back room of a saloon.

The district began to form with the arrival of the first forty-niners and thrived until the devastating quake and fire of 1906. Ironically, the buildings in this haven of heathens were largely spared by that catastrophe. Some buildings were torn down later, but the district is now listed on the National Register of Historic Places and thus protected. Most of Pacific Street—popularly known as Terrific Street when it was the main stem of the Barbary Coast—is now a quiet row of distinguished antiques dealers and architectural firms.

Walk Description

Start in

Portsmouth Square, which during the gold rush was the city’s main plaza. City Hall stood on Kearny Street from 1852 to 1895; it occupied the former Jenny Lind Theater, so named in honor of the Swedish Nightingale, who never performed in San Francisco. Next door was a grand gambling hall called El Dorado. The legendary Bella Union, the most popular of the city’s music halls, stood on Washington Street, just above Kearny.

The square itself was a barren patch of earth with crisscrossing footpaths converging in the middle. This is where important things happened in early San Francisco. In July 1846, the Stars and Stripes were raised here by Captain John B. Montgomery, formally claiming the settlement of Yerba Buena for the United States. (The town was renamed San Francisco a year later.) A plaque in the square commemorates the event. The square soon acquired the name of Montgomery’s ship, the USS Portsmouth. Another monument, featuring a cast bronze ship, commemorates a couple of visits by Robert Louis Stevenson, author of the classic tale Treasure Island. Having spent a few months in San Francisco in 1879, Stevenson returned in 1888 with his new wife, Fanny. From here they embarked on the extended sea voyage that would end with the author’s death in Samoa, six years later.

Now firmly part of Chinatown, Portsmouth Square looks nothing like it would have before 1906, but it is as vital as ever. It still attracts gamblers—on pretty much any day of the week, you’ll spot men gathered around park benches playing fevered games of cards.

Follow Washington Street in the direction of the bay, cross Columbus Avenue, and you’re entering the Jackson Square Historic District. Most of the brick structures here date to the 1850s and ’60s, when this area was the city’s exciting and dangerous nightlife zone.

The Transamerica Pyramid (which we examined in Walk 3, Financial District) stands on a historical site, that of the legendary Montgomery Block, commonly known as Monkey Block. As no-longer-extant landmarks go, this one was a doozy: built in 1853, the Montgomery Block was for a time the largest and most prestigious commercial building on the West Coast, but it’s not for commerce that it is remembered. A bar on the ground floor, called the Bank Exchange, gave the city its signature drink, pisco punch. Pisco is a Peruvian or Chilean brandy that perhaps was introduced locally by Chilean immigrants during the gold rush. To make pisco punch, pineapple was infused in gum syrup and mixed with water, lemon juice, and pisco to make an innocuous-tasting beverage that packed a wallop. It was commonly observed that the drink could “make a gnat fight an elephant.” The bar, alas, was done in by the Volstead Act in 1919, and the drink long ago fell out of favor. Of late, however, pisco punch has begun to reappear on drink menus around town, thanks to today’s inquisitive breed of bartenders.

As the city grew, the Monkey Block’s more status-conscious tenants moved down Montgomery Street, and artists, tradesmen, musicians, writers, and poets moved in. By the 1880s, the immense building was the center of the city’s bohemian life. In the basement was a public bath habituated by writers such as the young Mark Twain, who worked as a reporter in town from 1864 until 1866. (Twain, having deserted the Confederate Army in 1861, spent much of the ’60s in the West.) While bathing here Twain reputedly made the acquaintance of a fireman named Tom Sawyer and thought well enough of the name to use it in his best-known work. Ambrose Bierce, Jack London, and Robert Louis Stevenson all either worked in the building or had other excuses for dropping by. The building was finally demolished in 1959, and the site served as a parking lot for more than a decade before ground was broken for the Transamerica Pyramid.

Turn left onto Montgomery. This first block has numerous landmark buildings, most obvious being the Old Transamerica Building (701 Montgomery St.), a flatiron clad in white terra-cotta tiles. It was built in 1911 for A. P. Giannini, founder of the Bank of Italy, which grew to become Bank of America. It’s now the San Francisco headquarters for the Church of Scientology.

Across the street, at 710 Montgomery, the Black Cat Cafe was a famous hangout for arty bohemians from 1933 until 1963. In the 1950s, drag entertainer José Sarria gained notoriety for his live operatic performances here. A few doors down, at 716–720 Montgomery, Diego Rivera and Frida Kahlo lived and worked in fellow artist Ralph Stackpole’s studios on and off throughout the 1930s. Stackpole’s studios were the center of the city’s artistic social scene since the early 1920s, and for a time photographer Dorothea Lange subleased a photography studio upstairs.

The completely gutted building at 722 Montgomery was the office of lawyer Melvin Belli from 1959 to 1989. Belli, a flamboyant character, represented celebrity clients as diverse as Lenny Bruce, Zsa Zsa Gabor, and Jack Ruby. He also helped broker the deal that brought the Rolling Stones to the Altamont Speedway in 1969, and scenes were shot in Belli’s office for the documentary Gimme Shelter. He even appeared once in an episode of Star Trek, in which he played a character named Gorgan. Married six times, he passed away in 1996 at age 88. The building that once housed his firm was allowed to deteriorate after the 1989 earthquake, and its roof eventually caved in. In October 2009, the Belli family put it up for sale, priced at $10.5 million. It currently houses both residential and commercial space, including Filson, a Seattle-based purveyor of outdoor apparel and gear since 1897.

Turn right at Jackson, and half a block down you’ll reach the Hotaling Buildings (455 and 463–73 Jackson), which flank narrow Hotaling Place. Anson Parson Hotaling, who distributed liquor, among other goods, built the stately offices at 455 Jackson, then bought the second building, which he used as a warehouse for his booze. When the buildings survived the 1906 quake and fire, a jaunty little rhyme was composed by one Charles K. Field:

The building at 415–431 Jackson St. was built in 1853 and was formerly home to Domingo Ghirardelli’s chocolate company. In 1860 Ghirardelli added the structure at 407 Jackson. The older building, you’ll notice, has some intriguing details, with faces watching out from the frames of the upstairs windows. The much plainer 1860 building seems to suggest Ghirardelli had his mind more on the bottom line as his business expanded.

At Sansome Street turn left and then cut back up Gold Street. Considering San Francisco owed its good fortune to the gold rush, it’s interesting that Gold Street should turn out to be so inconspicuous. It’s a narrow lane, one block long, much of it walled in by the back sides of brick buildings. One entrance leads to

Bix, a spectacularly swank supper club that recreates the decadence and grandeur not of the Barbary Coast, but of the Jazz Age.

Turn right on Montgomery, then left onto Pacific Street. It’s an agreeable enough street to look at, with its perfectly silent historical buildings, but there’s little to suggest how terrific the 400 and 500 blocks were more than a century ago. However, saunter up the 500 block for a peek into the entry of No. 555, graced by some lovely nudes embossed in plaster. Think of this detail as an overt tribute to the neighborhood’s bawdy past. The building was once the location of the Hippodrome, a dance hall. The Hippodrome was across the street during its heyday and moved to this location after the first one burned down just in time for World War II, when the district enjoyed a minor revival, thanks to the influx of military personnel embarking from the city.

At the junction of Pacific, Kearny, and Columbus, look across Columbus and you’ll spot Francis Ford Coppola’s

Cafe Zoetrope (described in our next walk, North Beach) and the

Comstock Saloon, a lovely old establishment with a questionable past. While pre-Prohibition drink recipes are mixed and served on the original mahogany bar and antique fans stir the air, this genteel establishment is a far cry from its bawdy precursors. It opened in 1907 as the Andromeda and is now the perfect place to try the aforementioned pisco punch, the original Barbary Coast cocktail.

Head up Kearny toward Broadway. These are the declining remnants of modern sleazeville, with Kearny a lusterless adjunct of the Broadway striptease strip. Missing from this scene is the Lusty Lady, a rare worker-owned strip joint that shuttered in 2013. In the 1990s, the strippers here unionized and went on strike, and in 2003 they bought their bosses out. But waning revenue and rising rent forced them to close their peep-show doors a decade later.

At Broadway turn left. Based on the signs above the shops here, it’s obvious that this is a very sexy street. Broadway looks great at night, when the neon creates a reassuring tent of light that obliterates the darkness overhead. At the corner of Broadway and Columbus, the

Condor Club is once again a strip joint, after dallying in the food industry for the past two decades. In the 1960s it was the Taj Mahal of San Francisco’s burlesque scene, defined by the topless—and bottomless—act of the late Carol Doda (1937–2015). A plaque on the Columbus Street side of the building makes hay of two landmark dates: June 16, 1964, when Doda first unveiled the marvel that was her silicone-augmented bosom (which had reputedly ballooned from size 34B to 44DD); and September 3, 1969, when she first shimmied out of her skivvies on stage. Fondly remembered by old-time San Franciscans is the Condor’s sign, which featured a larger-than-life caricature of a bikini-clad Doda with blinking red lights for nipples.

The Condor, incidentally, was the site of a grisly death that made local headlines because of its salacious nature. One night after hours, in November 1983, a dancer and a bouncer were making love on top of a piano, which was supported by a hydraulic pole that was used to raise and lower it during performances. One thing led to another, the hydraulics were activated, and the paramours were crushed between the piano and the ceiling. The dancer survived; the bouncer did not. But they both lived on in tragic infamy.

Points of Interest

Portsmouth Square Kearny and Clay Sts.; 415-831-2700, sfrecpark.org/destination/portsmouth-square

Bix 56 Gold St.; 415-433-6300, bixrestaurant.com

Cafe Zoetrope 916 Kearny St.; 415-291-1700, cafezoetrope.com

Comstock Saloon 155 Columbus Ave.; 415-617-0071, comstocksaloon.com

Condor Club 560 Broadway; 415-781-8222, condorsf.com