Carlsbad, California had a number of notable events during the Prohibition era, including: bootlegger traffic, hidden speakeasy, Hollywood stars, Bing Crosby, Bob Hope and Frank Sinatra, Prohibition ended in 1933 and The Charles Kenneth Speakeasy in 2014

Prohibition Era in Carlsbad

Bootlegger Traffic

During Prohibition, Carlsbad’s Twin Inns, run by Eddie Kentner, became a strategic midpoint for bootleggers traveling between Los Angeles and Tijuana. Known for its hidden speakeasy, the Twin Inns had a call button at the back entrance specifically for bootleggers to discretely deliver alcohol for its guests. This setup allowed celebrities and locals in route to Agua Caliente to stop and discreetly pick up supplies or join in the secret festivities, helping to establish Carlsbad as a key stop along California’s covert Prohibition network.

Hidden Speakeasy

During Prohibition, the hidden speakeasy beneath Carlsbad’s Twin Inns hotel drew a crowd seeking the thrill of secrecy and forbidden cocktails. The space, managed by Eddie Kentner, was ingeniously designed to avoid detection, including an emergency butcher’s room to disguise illicit activities if the authorities came by. Guests would gather under the low-lit Victorian mansion to socialize, share stories, and savor outlawed liquor, knowing they could be interrupted at any moment.

Hollywood Stars

The speakeasy was a hang out for the rich and famous Hollywood stars, Bing Crosby, Bob Hope and Frank Sinatra.

Bing Crosby, famed singer and Hollywood star, became deeply connected to California’s social scene, especially in North County San Diego, where he frequently socialized with elite figures of his time. Although Bing Crosby didn’t own or operate a speakeasy during Prohibition, he did later contribute to the area’s social landscape by creating Bing’s Bar at The Inn at Rancho Santa Fe. Designed in a speakeasy style, Bing’s Bar embodied vintage luxury with rich wood paneling, plush seating, and a cozy fireplace, recreating the ambiance of clandestine gatherings typical of the 1920s and ’30s.  This speakeasy had clandestine touches, including an emergency butcher’s room to disguise its activities if authorities arrived. Patrons accessed it through a concealed entry, savoring the ambiance and excitement of a Prohibition-era bar

Crosby and other Hollywood legends like Charlie Chaplin and Mary Pickford were known to spend time at The Inn, which served as an exclusive retreat away from Los Angeles. This legacy has continued, as the bar and surrounding property have been carefully restored to evoke the glamour and sophistication of its Prohibition-era roots, providing a modern homage to the old speakeasy atmosphere that Crosby admired

Bing Crosby, a major figure in entertainment and an influential character in Southern California, significantly impacted Carlsbad’s social scene. Known for his love of golf, Crosby co-founded the Del Mar Thoroughbred Club in 1937, bringing Hollywood’s elite to North County. His Rancho Santa Fe residence, not far from Carlsbad, served as a retreat where he hosted many of his famous friends. Crosby’s love for privacy drew him and other celebrities to Rancho Santa Fe, making it a haven for those seeking refuge from Hollywood’s demands.

At the La Costa Resort in Carlsbad, where Crosby and other stars like Bob Hope and Frank Sinatra were regulars, the atmosphere echoed the exclusivity of a speakeasy with lush, secluded surroundings and high-profile events. Crosby even started his famous “Crosby Clambake” (now the AT&T Pebble Beach Pro-Am), which began as an informal gathering of celebrities and golfers​. Crosby’s influence in the area and Rancho Santa Fe’s allure for Hollywood’s elite helped shape North County as a glamorous retreat, where entertainers could escape the spotlight, mirroring the speakeasy’s atmosphere of intrigue and exclusivity.  Other top celebrities of the time like Corinne Griffith, Douglas Fairbanks, Sr. and Mary Pickford, and then later, Victor Mature of “Samson and Delilah” fame, as well as Robert Young of “Father Knows Best” became residents of Rancho Santa Fe. The former Crosby estate is still located off Via de la Valle across from the Morgan Run Golf Club and Resort in Rancho Santa Fe.  Prohibition ended in 1933, which brought an end to the rumrunning trade and the war against Rum Row.

The Charles Kenneth Speakeasy:

The speakeasy was rediscovered by Carlsbad chef Rob Ruiz (Land & Water Company Restaurant) during renovations to the building in 2014. Ruiz opened a speakeasy called The Charles Kenneth in the space, named after his grandfather, Captain Charles Kenneth Ruiz.  Ruiz wanted to share the original, prohibition era, bar with his guests.  The Bar had been hidden from the public, and not a concept, but a historical space of provenance. It is original, classic and timeless. An Oceanside native, Ruiz heard tales of the speakeasy growing up, which were confirmed when he found old coins and liquor bottles in the space during restoration.