11 Reasons to Visit San Francisco’s Most Notorious Neighborhood

A living testament to the community and the creative souls who live here, the Tenderloin National Forest (TNF) is the perfect place to begin the practice of becoming an observant visitor. It’s tucked away in an alley that once was filled with dumpsters. Residents transformed it into a harbor from busy streets. The first tree planted, a giant redwood, is now a 25-year-old threatening to grow beyond the strict 40-foot height caps in other old neighborhoods.

The city boasts that every resident lives within a ten-minute walk to a park, but with truncated hours, it depends on the day. The TNF is a statement to the lack of green spaces, and residents continue to agitate for more greenways. Go around lunchtime Wednesday through Saturday for a chance to look at the birdhouses, admire the Ohlone-inspired rock mosaic on the forest floor (artist: Rigo 23), and catch the occasional concert.

The Historical Marker Database maps where to find nine easy-to-miss sidewalk tombstones that include the lost library of 15,000 volumes at B’nai Brith, the birth of porn, a suffragette dance hall, and more. Wander at leisure and discover nine locations lost to time and politics.

The Bulldog Bathhouse was a victim of hideous prejudices during the AIDS crisis; you might picture the second-floor mock prison with real cells where gay men could act out fantasies. The California Labor School sent its famed Chorus to serenade picketers but was destroyed by the red scare. Black Hawk jazz greats like Miles, Billie, and the Bird played to both adults and children, the latter separated by chicken wire to comply with underage audience laws. As poet Jamaal May wrote of Detroit, there are birds here still, and even the tall fences on what’s now Boeddeker Park hide steel flowers by artist Amy Blackstone.

Bordering the Tenderloin to the southeast, Market Street is dotted with the public’s “favorite street furniture,” according to a board of supervisors’ 1991 meeting. The Path of Gold is a string of 327 light standards, highly ornamental cast iron light poles with glass sodium vapor lamps. The bases feature Arthur Putnam’s imperialist 1916 artworks fittingly titled “The Winning of the West.”

Look closely at the bases for pumas, prospectors, and pioneers; these replicas were installed in 1972, but an original sold in the last decade for over $3,000. When trolleys expanded, the overhead wires weren’t a lick popular; the deal brokered by infamous corrupt politician Abe Ruef involved lining the street with Beaux Art lamps that would illuminate retail spaces. His exploitation and bribery highlight how seediness was increasingly associated and subsequently wrongly attributed to the TL.   

An unusual building sticks out on Geary. The exterior of this 1917 building was commissioned by the Ancient Arabic Order Nobles of Mystic Shrine. The Shriners are a fascinating secret fraternal order who borrowed heavily from Islam and this was their temple. Contemporaries described the façade as something that looked like it grew from crystallization—“mineral kingdom” is an apt description of the ornate decorations.

The architect, T. Patterson Ross, allegedly requested to put his name on the cornerstone and was denied. Arabic letters are traditionally used only for specific sayings and عظيم هو الله ، وعظيم روس المهندس المعماري would be fairly easy to spot over the entryway, but the legend hasn’t been substantiated. Inside, there’s a theater that hosts delightful cabaret and Broadway, and an appointment-only art gallery hosts a collection of local contemporary art.  

Dubbed the last LGBTQ+ bar in the Tenderloin, this treasured relic is open daily. This corner of the Tenderloin is the first legally recognized transgender district. Outside, pride flags line the streets and nearby is a plaque devoted to an August 1966 cafeteria riot preceding Stonewall.

The police brutality against trans women ignited rapid social change and a strong peer support network, all enabled by increased unity amongst LGBTQ+ activists. Drag queens honor the roots of survival sex work and police brutality, and a trip to Aunt Charlie’s is a testament to the roots of LGBT activism. Catch a drag show and enjoy the unique performances from queer golden girls whose aging is the subject of a fabulous 2014 documentary by James Hosking.

Tickets sell out fast for the comedic shows at this local theater. It’s the former home of Original Joe’s, but these days you can catch American bites and well-made cocktails from sharply dressed bartenders while you wait for the show. Carry those fancy drinks inside, because the golden velvet seats are comfortable.

Check out a semi-regular show called Tinder Disrupt to watch performers use PowerPoint presentations in a dating show. You may end up married like one couple who met through the show, but one thing’s for sure: you’ll fall in love with this uniquely SF show.

By appointment or luck, find yourself in this celebrated vintage pulp bookshop that plays with the idea of ephemeral culture. The books are smutty and sexy, and while some may be rare and expensive, you’ll also find bargains in sections like “Catholic Guilt.” You might start to see why author Richard Price, also known for creating Michael Jackson’s Bad music film, called this destination the “congressional library of historical sleaze.”
In a neighborhood that once inspired Dashiell Hammett’s hardboiled detective stories, a bookstore full of pulp is the perfect complement to reading up on the secret gay bar tunnels, corrupt police, and scandals of the Tenderloin. Even if developers claim the tunnels are fiction. Oh, and John Waters says it’s the only reason he keeps an apartment in SF.

Emperor Norton’s Boozeland is a gilded and gorgeous escape that is the perfect blend of folklore and history in a self-described “royal playground for derelict citizens.” Knowing the whimsical real-life Norton, who declared himself emperor in 1859 via a charming letter to a local newspaper, makes the drinks bittersweet.

His Majesty was once arrested on accusations of being mentally unsound, but the city rallied to pardon him so that he could once again “remedy the evils” of the city with his proclamations. A majority of SF’s mental health, substance use disorder, and housing insecurity facilities are concentrated in the Tenderloin. Remember that the folks you pass on your way to this playground are neighbors, too.