It is hard to imagine Castro Street without its iconic rainbow flag, but when Trevor Hailey (1941–2007) created Cruisin’ the Castro walking tours, such symbols of the LGBTQ community were largely absent from the neighborhood, outside of what LGBTQ residents dared to display. Hailey, however, had a bold idea that she revealed at just the right moment.
Steve Adams, Senior Vice President of Sterling Bank who in the ’90s was president of what was then called Merchants of Upper Market and Castro (now Castro Merchants), vividly recalls that moment.
“During a walking tour of the Castro with then Mayor Willie Brown in 1997, Trevor looked into the eyes of the Mayor and with great convincing passion said that a rainbow flag should permanently fly in the Castro,” Adams 
told the San Francisco Bay Times. “Brown turned to Dean Goodwin, his official liaison to the city’s gay community, and said, ‘Make it happen!'”
And so it did.
On November 7, 1997, which was the 20th anniversary of Harvey Milk’s election victory in the race for Supervisor of the 5th District (which then included the Castro), Mayor Brown raised a 20’x30’ rainbow flag on a 70-foot-tall flag pole in Harvey Milk Plaza. The flag raising happened during a ceremony to mark the Milk anniversary. A rainbow flag has been proudly flown in the Castro ever since, with smaller ones later added to the district.
Hailey didn’t stop there. She worried that Milk’s former camera shop at 573–575 Castro Street between 18th and 19th streets could be lost. She therefore suggested that it should hold landmark designation, and organized others who shared her view. On February 24, 2000, the city’s Planning Commission unanimously voted in favor of the idea. The 1894 wood-frame structure was saved, and now houses the Human Rights Campaign Action Center and Store.
“Trevor could be feisty and opinionated, but she had a Southern charm about her and was very persuasive,” Adams said. “I think of her every time I look at the rainbow flag.”
Members of our team often think of her too, remembering her distinctive voice echoing through every corner of the Castro.
“Follow me!” Hailey would command while bolting down side streets off the busier corridors of Upper Market as she pointed out some interesting nugget of queer history. “You didn’t read about this in your history books in school, now did you?” she would knowingly ask. Like a San Francisco Gay Men’s Chorus concert under the capable baton of Dr. Tim Seelig, she could somehow pack stories of both great humor and sadness into an experience lasting just a few hours. She would take you along on the emotional ride and was so captivating that the time would just fly by.
When Hailey passed in 2007, shortly after selling her tour business and moving out of San Francisco, the Castro’s rainbow flag was flown at half-mast. It was a fitting tribute to the visionary who helped both to enrich and save the history of San Francisco’s LGBTQ community.
To view a series of videos highlighting Trevor Hailey and her legacy, go to: https://www.youtube.com/user/OnlyintheCastro
Cruisin’ the Castro Walking Tour’s “Historical LGBTQ Tour” offers a fascinating 2-hour look at the past, present and future of LGBTQ civil rights in America from a San Francisco perspective. If you have never been on the tour, we strongly encourage that you do so. Even if you are a longtime resident or have been on the tour in years past, you will likely learn something new, refresh your memory and fall in love all over again with our community and its living history.
Among other experiences, you will:
Highlights include everything from “Hank’s Infamous Bill Doll Collection” to Castro’s colorful murals that you probably have walked by many times but might not have stopped to properly study. Once you book your reservation online
( https://bit.ly/2YAas4w ), tours meet at the Rainbow Flag pole at the corner of Castro & Market Street near 400 Castro. They cost just $25 per person, and are free for children under 5 years of age.
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