San Diego’s Stingaree District: Saloons, vice, and the rise of the Gaslamp Quarter

In the late 19th and early 20th centuries, San Diego’s downtown waterfront, roughly the blocks south of Market Street between 1st and 5th avenues, was known as the Stingaree District, the city’s most infamous concentration of saloons, gambling halls, opium dens, and brothels.

What’s in a name?

The name “Stingaree,” believed to derive from “stingray,” was associated in local lore with visitors who were said to get “stung” by the district’s vices and chaos.

By the 1880s and 1890s, the Stingaree had become synonymous with waterfront vice. A San Diego Union reporter described the scene in an 1887 account after walking Fifth Avenue at night:

View of buildings at the corner of 3rd Avenue and J Street in an area which has been called Chinatown and Stingaree in 1924. Pioneer Trucking Co. is seen behind the Stingaree wood buildings in the background. (Photo courtesy of the San Diego History Center)

“Strolling down Fifth in the evening, the ear is rasped by notes from asthmatic pianos, discordant fiddles, and drunken voices boisterously singing ribald songs … the eye is pained to see men lying drunk on every corner … it is fully as bad as the Barbary Coast in San Francisco.”

Opium dens operated alongside saloons and brothels, many setting up shop near what was then San Diego’s Chinatown on the southwest edge of the district. Immigrant communities lived and worked in the same dense blocks that housed gambling rooms, small businesses, and vice establishments.

Saloons, and more

According to the San Diego History Center archives, the Stingaree at its peak contained dozens of saloons and more than a hundred vice-related establishments, making it one of the most active red-light districts on the West Coast.

Some establishments gained notoriety beyond San Diego. Locations such as the Pacific Squadron at Second and J Streets and the Dewey and Little Casino at Third and Island were frequently cited in historical accounts of the era. Local reporting and municipal records from the period noted concerns about drug activity, including cocaine, morphine, and opium circulating through parts of the district.

sting 3 — View of a copy of a newspaper front page from the San Diego Union newspaper in November 1912, where 138 women were arrested in the Stingaree Raid. Stingaree was also known as the Red Light District. Walter Bellon sought to clean up prostitution, saloons, gambling, and other activities. (Photo courtesy of the San Diego History Center)

Red light

Within the Stingaree, prostitution was widespread, and many women became known by nicknames that appeared in later historical accounts. Ida Bailey, one of the district’s best-known madams, operated the Canary Cottage, remembered in local histories for its reputation and relative refinement compared to surrounding establishments.

By the early 1900s, reform movements tied to the Progressive Era began targeting the district. Historical accounts note that hundreds of women were working in prostitution in the area at its peak, and city officials increasingly turned to raids, closures, and health enforcement to suppress vice activity.

Between roughly 1912 and 1916, large portions of the Stingaree were demolished as part of a broader downtown cleanup effort ahead of the 1915 Panama-California Exposition. Entire blocks were cleared, and much of the district’s physical footprint disappeared.

Long gone

Today, the Stingaree no longer exists as it once did, but its history remains embedded in downtown San Diego’s Gaslamp Quarter, where restored Victorian-era buildings now sit above one of the city’s most infamous former neighborhoods.

sting 4 — On the right, a view of a two-story building on the northeast corner of 4th Avenue and J Street in Stingaree and Chinatown area in 1973. The building was used by Goodwill in the 1970s or before. The building was not standing in the 1980s. On the left, a view of the Stingaree district of downtown San Diego. The Stingaree district was located in the area of 3rd Avenue and Island Avenue. This view is looking at the west side of 3rd Avenue south from Island Avenue in the early 1900s. (Photos courtesy of the San Diego History Center)

Read more history stories here and send an email to DebbieSklar@cox.net.

Sources:
San Diego History Center – Stingaree district and vice history collections
Voice of San Diego – historical reporting on downtown cleanup and redevelopment
San Diego Reader – historical features on the Stingaree District
Library of Congress Prints & Photographs Division – historic San Diego images and maps

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