The San Diego Pride Parade marks its 50th anniversary this year. It’s one of the largest and oldest Pride celebrations in the country, and it's almost time for the big celebration to begin. The Pride Parade and Festival symbolizes the progress made by San Diego’s LGBTQ+ community.
But as flags are waved and as the good times roll, it’s worth remembering that an important part of local LGBTQ+ history is not found in Hillcrest.
It’s a few miles away, in Point Loma — across the street from Liberty Station. It’s a below ground bar originally called The 19th Hole, a tip of the hat to the golf course across the street, which has also been here for a very long time.
“1924 is as far back as we could find any records of its existence," Karen Sherman said. She’s owned the place since 2000, but she took over running it in 2015.
“It was started by some Navy wives who were avid golfers and just wanted a place of their own to hang out … but they didn’t legitimately have it until 1933 when it was the end of Prohibition, so it was a bit of a speakeasy during that period of time," Sherman said.
Sherman said it was The 19th Hole until a big storm in 1951 blew down the sign, and sometime after that, it began to be known simply as The Hole. The bar’s newest logo, shown on the sign in front, is an homage to its original name.
“I’m very proud of it. I’m proud of its heritage," Crosby Roper said. He's the general manager here. He’s also Karen Sherman’s son.
“Family and business is always a little bit rough, but we both love each other and despite everything, we always have each other’s back," Roper said.
And mother and son share a mission when it comes to The Hole; a common purpose.
“This bar is such a part of the community and it’s so important to the community and so to me that’s what its attraction was," Sherman said.
“Seeing the community come together, seeing people that may not have a lot in common find common ground and be able to reach each other on a human level," Roper said.
Long before the internet, gay bars were the primary places, safe spaces where the LGBTQ+ community came together.
“That was kind of where what we know today as a gay community kind of evolved," Art Smith said.
Smith is a historian of sorts. He founded and runs the “Gay Barchives,” an online compendium of gay bars past and present. In an interview from his home in Florida, he said The Hole is like a lot of gay bars across the country that were established near military installations. You may know that Liberty Station used to be the Naval Training Center, and of course the Marine Corps Recruit Depot is still around — just down the street.
“These people, for the first time, were displaced from their families. You know, if you think about our history as a country for decades and centuries even, people stayed close to home ... but when the war came along and all these people were drawn out — when they came back — they found themselves in a new environment and got to explore a new aspect of themselves. So I guess we can kind of give the war some credit for the evolution of the gay community," Smith said.
Smith went on to say that The Hole is at least the third oldest gay bar in the country. He said it very well may be the oldest. The problem, he said, is that it’s hard to pin down dates of when gay bars actually opened.
“So we have to rely on documents like police raids, exposés in the media, a variety of different things — military notices because the military was infamous for banning people from going to bars that they suspected were inappropriate places for military, which usually meant they were gay or lesbian," he said.
One thing Smith said is certain; The Hole is the oldest gay bar that’s always operated in the same place.
The Hole's impressive history aside, there are the day to day challenges and annoyances of doing business here. One of them popped up while we were interviewing Roper.
“I apologize for the plane noise … the Point Loma pause as we all call it," he said.
Like many homes and businesses in the Point Loma area, The Hole sits right under San Diego International’s takeoff flight path. But what you might think is a negative, Karen Sherman said — is actually a positive.
“The airplanes in some ways have saved us from noise complaints because everyone around here, every residential unit around here and commercial unit around here, took advantage of the FAA’s noise mitigation measures — the quieter homes program," she said.
We shot this story late Thursday afternoon. At that point, the rugby and softball team sponsored by the bar were on site. But as the sun set, things picked up — there was karaoke. Chris Woodward has hosted it here for nine years.
“It’s just a really caring and open environment where people can come and feel safe and have a good time," he said.
From pre-Prohibition to the supposedly dry years of Prohibition, to World War II, right through the rest of the 20th century and a quarter of the way through the 21st, San Diego’s oldest gay bar survives as not only a repository of local LGBTQ history, but also a place to feel safe, to be in community, and to have a good time.
