The Hole in the Wall (1924 – now) is San Diego’s oldest gay bar. A staple of San Diego’s LGBTQ+ community for decades, The Hole reportedly opened as a speakeasy in 1924 across Lytton Street from the six-hole Sail Ho golf course at the Naval Training Station (now Liberty Station). Construction on the naval station began in 1921, with San Diego architect Frank Walter Stevenson’s designs in the Mission Revival style. It was commissioned on June 1, 1923.
The bar sits in a depression dug in the early 1900s to access an aqueduct that ran between Mission Bay (then called False Bay) and San Diego Bay. The stairs at the Hole’s entrance — a nondescript wall north of the old Bottle Barn liquor store building — descend into a tropical garden patio.
“It was started by some Navy wives who were avid golfers and just wanted a place of their own to hang out,” says proprietor Karen Sherman. “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.
By the 1930s, on that spot across the street was the Montemar Golf Fairway, a driving range and putting course. The fairway was owned and operated by golfer Harry A. Jacobs, managed by Charles Bruce and William “Bill” Anger. Jacobs also owned the Uptown Fairway located at the foot of Ash Street. Montemar held tournaments, offered lessons by golf pro Joe Ezar, and had a cafe under various names for years — before the Catholic church bought the course and built the St. Charles Borromeo Academy in 1947.
Naval officers from the Sail Ho club routinely played members of Montemar and the Balboa Park Golf Club. One notable player was Chet Tobey, who opened Tobey’s 19th Hole Cafe at the Balboa course. (Still in business and still run by the Tobey family today!)
“Totally Different,” the Montemar Cafe was an attached restaurant serving breakfast, lunch and dinner — with home-made pies, cakes, hot biscuits. “Lady cooks, reasonable prices.”
For a time, it became Murphy’s Beer Garden, then Jim’s Eat Shop run by Jim and Eileen Quinn. Ultimately, it was known as The 19th Hole, with a humorous nod to the nearby Sail Ho course.
In the 1940s, it was one of the “secret handshake” bars in San Diego, well-known to its gay clientele, but also to many others, including the press and police. So much so that the place was listed as off-limits to all military personnel.
“Doris Dazzle doesn’t play golf. But she went to the links with her boyfriend and played the 19th hole,” went one anonymously homophobic bit the the San Diego Union in 1946. “How did you find the 19th Hole?” the reporter asked. “‘Oh,’ she replied. ‘I just followed the swallows.’”
When ownership changed in the 1960s, The Hole became one of San Diego’s first openly gay bars. Its name was by then simplified tongue-in-cheek to “The Hole.” In 1964, the first mention of “The Hole” appeared in mainstream newspaper classified ads placed for bartenders, barmaids, and even a piano player. Burgers and frosties were offered through a “serve-thru” counter.
Throughout the 1970s and 1980s, The Hole was a popular, safe hangout for the LGBTQ+ community. During this time, the formidable Hole Sunday Beer Bust was born. Fresh fried chicken was initially served, which morphed into a California-style barbecue and “best chest contest” that now draws over 600 guests every Sunday.
Fun fact: In the 2000s, The Hole’s patio was home to the Darkwave Garden, with DJs spinning Goth pop music!
In 2015, Karen Sherman and Roger Hull bought the dive bar and renamed it The Hole in the Wall. It is operated today by Sherman and managed by her son, Crosby Roper. This year, The Hole marks its centennial during the San Diego Pride celebration. It is considered by some to be the third-oldest gay bar in America, and Sherman boasts that it’s “the oldest gay bar that’s always operated in the same place.”
As one writer from Vice reported, “This place has conjured a weekly horde of the most unpretentious, unrepentantly fun dudes known to gay mankind.”
Cash bar with inexpensive well drinks, pitchers of beer, pool table, karaoke, and a garden patio.
Loma Portal
2820 Lytton Street
San Diego, CA 92110
19th Hole speakeasy (1924 – 1933, need info…)
Murphy’s Beer Garden (1934, need info… )
Montemar Cafe (1938, Harry A. Jacobs)
Jim’s Eat Shop (1947, Etta and Hubert Smith, James and Eileen Quinn, Marie Daley)
The Hole (1961)
The Hole (1982, Robert Cooper, George Mitsven, Donald Powell)
The Hole (1987 – 1994, Jay C. Rasmussen)
The Hole (1995 – 1998, Wamsley Inc, Jay, Robert, and Lois Rasmussen, David Jones)
The Hole (1998 – 2015, Family Taverns Inc, Debra Williams, Stephen Rock, Lois Gregor)
The Hole in the Wall (2015 – now, Lytton Partners LLC, Karen Sherman, Roger Hull)
Notes:
Citation: Martin S. Lindsay. ‘The Hole.’ Classic San Diego: tasty bites from the history of America’s finest city. Web. < https://classicsandiego.com/restaurants/the-hole/ >
Sources: “Point Loma’s Historic Gay Bar The Hole To Close After Final Beer Bust On July,” SanDiegoVille, 28 Mar 2015; Tyler Trykowski, “Scenes from The Hole, San Diego’s Most Glorious Gay Bar,” Vice, 13 Jul 2015; John Carroll, “San Diego’s Oldest Gay Bar Turns 100,” KPBS, 17 Jul 2024.
“Charles Bruce, manager,” is from San Diego City Directory, 1937, San Diego City Directory, 1938, pg 456.
“Montemar Fairway, William O. Anger, manager, Golf Fairway, 2820 Lytton, opposite Naval Training Station, telephone Bayview 9238,” is from San Diego City Directory, 1937, pg 423.
“Totally Different,” comes from Joe Hernandez, “First Elimination Contest is Planned at Driveway,” San Diego Evening Tribune (San Diego, CA), 12 May 1931, pg 19; classified display ads, San Diego Evening Tribune (San Diego, CA), 11 Jun 1938, 12 Jun 1938.
“Montemar Fairway, 2820 Lytton St,” address from “Golf Clubs and Courses,” San Diego City Directory, 1938, pg 1093.
“Montemar Fairway, Dorothy B. Fulton, manager, 2820 Lytton,” San Diego City Directory, 1939, pg 391; and “Montemar Fairway, 2820 Lytton St,” from “Golf Clubs and Courses,” San Diego City Directory, 1939, pg 971.
Joe A. Calwell operated the Fairway by 1940. “Montemar Fairway (Joe A. Calwell), golf, 2820 Lytton,” is from San Diego City Directory, 1940, pg 434; and “Montemar Fairway, 2820 Lytton St,” from “Golf Clubs and Courses,” San Diego City Directory, 1940, pg 1058.
“Leon Wilson, attendant, Montemar Golf Driving Fairway, 2820 Lytton,” San Diego City Directory, 1941, pg 805.
In 1941, the Unionroom fell vacant and was for sale. “Owner called away.” Navy housing projects and the new 150-home Montemar Ridge development began to encroach upon the course’s space. “Johnny Bellante, La Jolla Country Club professional, and Harry Jacobs have sold out their partnership in the Montemar Driving Fairway, near the naval Training Station, to Bob Foster, local businessman,” classified ad, San Diego City Directory, (San Diego, CA), 03 May 1941, pg 20; “Par-A-Graphs,” San Diego Union (San Diego, CA), 06 Sep 1941.
“Robert E. Foster, golf driving course, 2820 Lytton,” from San Diego City Directory, 1942, pg 298.
“Robert H. (Gada) Colerick, restaurant, 2820 Lytton St,” and “Cecil C. (Jewell) Colerick, manager, restaurant, 2820 Lytton St,” are from San Diego City Directory, 1943, pg 225.
“Doris Dazzle,” comes from an anonymous bit on a San Diego sports page, with a not-so-subtle nod to The 19th Hole’s demographic. “Northeast Corner,” San Diego Union (San Diego, CA), 20 Aug 1946.
St. Charles Borromeo Parish was established in 1946, the St. Charles Borromeo Academy is built on part of the site of the Montemar Golf Driving Fairway. On the front lot was Jim’s Eat Shop. The buildings at 2820 Lytton surrounding its garden patio were built in 1946. On 20 Jan 1947, owners Etta M. and Hubert T. Smith applied for a liquor license. That summer, Eileen Quinn applied for an on-sale beer license. Etta and Hubert Smith, “Notice of Intention to Engage in the Sale of Alcoholic Beverages,” San Diego Union (San Diego, CA), 20 Jan 1947; Marie Daley, “Notice of Intention to Engage in the Sale of Alcoholic Beverages,” San Diego Union (San Diego, CA), 10 Apr 1947; San Diego Union (San Diego, CA), 11 Feb 1982.
“Jim’s Cafe” also known as “Jim’s Eat Shop” was run by Jim and Eileen Quinn. “James M. (Eileen L.) Quinn, restaurant, 2820 Lytton St,” from San Diego City Directory, 1947, pg 909; Eileen Quinn, “Notice of Intention to Engage in the Sale of Alcoholic Beverages,” San Diego Union (San Diego, CA), 07 Jun 1947.
In 1948 Jim Quinn was arrested for selling alcohol to three under-age Naval Training Center sailors, and in 1953, James C. Brown of 2820 Lytton was cited for selling alcohol to a minor. “Hearing Set for Bars Named in Minor Sales,” San Diego Evening Tribune (San Diego, CA), 05 Mar 1953.