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The Tenderloin

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Make no mistake: This is the city’s down and dirty side, and it’s neither shy nor ashamed of it. Still, for those brave (and cautious) enough to venture down its funky but somehow charming streets, there are treasures to be found.

History: Nobody can quite agree on where the Tenderloin got its name, but the most popular legend is that old-time San Francisco cops earned pay raises for the occasional steak dinner by walking beats here- or by accepting some petty bribes on the side. Every story makes it clear that the Tenderloin has always been the seedy side of San Francisco.

Don’t Miss: The recently opened Tenderloin Museum is a small outpost of culture chronicling the long and colorful history of the neighborhood in terms that celebrate its sketchy reputation. The Great American Music Hall is San Francisco’s oldest music venue and still one of its most beautiful. Chambers Eat + Drink can be hard to find (it’s in the Phoenix Hotel) but provides secluded class and fine dining near the strip of the neighborhood known as Little Saigon. And every Sunday, Glide Memorial Church, which has served San Francisco and the Tenderloin for going on 90 years, sings, claps, and swats with its famous and inspiring Glide Ensemble.