The plentiful secrets and techniques of San Francisco’s oldest alley

Next time you’re walking around the downtown end of Columbus Avenue, take a turn down a narrow one-block alley named Hotaling Place. Rather than staring up at the towering Transamerica Pyramid, look down between your feet, and you’ll see parallel waving lines etching the pavement along the quiet, narrow block. Those lines mark the old city shoreline, before hundreds of abandoned ships formed new land claiming the bay, when San Francisco was a very different place.
Hotaling Place may be the most unique street in the city and holds centuries of secrets that are rooted in a time when it wasn’t called San Francisco, or even America.
The little fishing village of Yerba Buena was part of Mexico until July 9, 1846, when US Navy officer John B. Montgomery landed his ship on this shore and planted an American flag at what is now Portsmouth Square (named after his ship).
Within two years, with the end of the Mexican-American War, the land became part of the United States, and Yerba Buena was renamed San Francisco.
Hotaling Place, San Francisco.
Andrew Chamings
The Gold Rush that followed changed the growing town beyond all recognition. Its population grew from 1,000 to 25,000 in a year, with thousands more forty-niners leaving ships abandoned there and heading to the Sierra Nevada for gold. Those 500 ships and newly built wharves grabbed some 50 city blocks from the water. This old buried shoreline lies where Hotaling Place’s line curves along the alley.
The street earned its name from pioneering entrepreneur Anson Parsons Hotaling, who built his exquisite Italianate business headquarters at 451 Jackson St. in 1866. (Hotaling also owned Hotaling Annex West across the street. That later became a gathering place for artists and writers in between their work shipbuilding during World War II.) In the early 1900s, Hotaling’s chief line of work was booze, and his company was described as “the biggest warehouse for booze in the west.” Gallons of whiskey were stored there when the earthquake hit in 1906, and while nearly every building in the area was razed by the shake and subsequent fire, Hotaling’s whiskey store somehow survived. Archives report that a mile-long fire hose that ran from Fisherman’s Wharf extinguished the flames.
The Oakland Tribune, May 17, 1906.
Archival/Oakland Tribune
Hotaling, an opportunist who knew how to make a buck, promptly ran ads in Bay Area newspapers after the quake boasting that his liquor reserve survived, and if readers sent money he would ship them his “Old Kirk” whiskey. Though, likely due to the destruction of the city’s bank offices, he requested only “coin,” noting that “checks and exchanges are useless at this point.”
For those inclined toward the supernatural, a story shared on a ghost tour of the alley tells of a stampede of cattle rushing down the narrow street on a foggy day. The ghost cows are said to be the specters of the livestock that ran through the city during the chaos of April 1906.
Hotaling Place, San Francisco.
Andrew Chamings
While it’s impossible to verify if this actually happened on this street, there were instances of cattle fleeing their pastures across the city in Cow Hollow and running through the smoldering ruins. It was an eerie sight amid the darkest days of San Francisco. As one police officer described to the press: “The noise and the dust, and the feeling of destruction, all combined to daze a man. All about us houses were tumbling, and falling walls and chimneys and cornices were crushing men and horses in the street.”
(In other bovine-related earthquake incidents, the New York Times reported shortly after the disaster that a cow in Point Reyes was swallowed whole by a crack in the earth on the San Andreas Fault.)
The street was also known for the horse stables at 32-34 Hotaling. The alley was a hub for horse-drawn streetcars that used the road and stables as a turnaround point.
Hotaling Place, San Francisco.
Andrew Chamings
One of the most stunning structures still standing, which feels like it could line a cobbled alley in Victorian London, is the red-brick back entrance of what is now the Barbarossa Lounge, which fronts onto 714 Montgomery St. That structure also reportedly survived the earthquake And, similarly to Hotaling, an advertisement for the grocers that operated there in San Francisco’s Italian newspaper, L’Italia, in October 1907 said they continued to sell “excellent and select liquor.”
Neighboring that building is a somewhat foreboding brick structure that has housed private members club Villa Taverna since the 1950s. Between two medieval-looking lanterns, a goddess with wheat and snakes (this appears to be Demeter, the Greek goddess of the harvest) looks out over the alley, ensuring only those with invitations pass through the doors. The marble sculpture was erected above the doors in the 1950s, and the owner claims it was an ancient Roman piece gifted by the Italian government.
Hotaling Place, San Francisco.
Andrew Chamings
That building backs onto 716 Montgomery, another structure as old as the city; it was built in 1849 from the wreck of a ship named The Georgean. That building became an art studio after the earthquake and was visited by Frida Kahlo, according to historian Nancy Boas.
The street is now lined with art galleries, designer showrooms and high-end clubs, but until as late as the 1970s, Hotaling Place was described as a “dirty little old alley” in the press, as it had been for years.
After the earthquake in 1906, religious leaders in San Francisco blamed the Barbary Coast’s vices for the disaster, declaring that the event that took thousands of lives was a wrathful God’s retribution on the dirty town.
Hotaling Place, San Francisco.
Andrew Chamings
One plaque, on the corner of Hotaling and Washington today, quotes the words of poet Charles K. Field on finding the building undamaged after so many churches crumbled.
If, as they say, God spanked the town
For being over-frisky,
Why did He burn His churches down,
And spare Hotaling’s whiskey?