San Francisco was crazy during the '60s the 1860s, that is. Back then the city's beer halls and saloons were fueled by the gold-lined pockets and salty tongues of sailors, pimps, con artists, and whores. The city is actually pretty tame compared with how it used to be. Prostitutes no longer hang naked from windows, and bartenders have stopped drugging clients and selling them into indentured servitude on the high seas. About all that's left from those early dens of debauchery are a few brass rails and some nice pieces of carved mahogany, to be found in the city's oldest bars. Although many of the original bars at these establishments perished in fires, as soon as the ashes settled, people picked up the pieces and got right back to boozin'. The Saloon, Buena Vista, and Little Shamrock are your best bets for wetting your whistle above the same wooden counters where gold miners and shanghaiing sailors once drank.
The Buena Vista (2765 Hyde, SF. 415-474-5044, www.thebuenavista.com), which concocted the first Irish coffee, rates as San Francisco's second oldest bar. An 1889 photo of the business shows its former location, across the street. When that building was damaged by the 1906 earthquake and fire, the café moved to its present spot, taking its rich mahogany bar with it.
Proud to have been a speakeasy during prohibition, Cafe du Nord (2170 Market, SF. 415-861-5016, www.cafedunord.com) which opened its doors in 1907, before hooch was outlawed retains its scary escape tunnel, now dead-ended, and has the nicest original, hand-carved bar you'll find in any Bay Area basement.
A local historian from E Clampus Vitus, a secret SF historical society, scoured old city directories and traced boozing on the corner of 16th and Guerrero streets, where Elixir (3200 16th St., SF. 415-552-1633, www.elixirsf.com) currently hangs its sign, back to 1858. The place has gone through a number of hands it was called Swede's from 1865 to 1885 and was leveled with the rest of the hood in the fire of '06, but it's always been a bar. Of course, during Prohibition it was officially know as a soft drink parlor.
The Hotel Utah (500 Fourth St., SF. 415-546-6300, www.thehotelutahsaloon.com) which was once called Al's Transbay Tavern, appeared in Dirty Hairy, and served President Richard Nixon, Joe DiMaggio, and Marilyn Monroe has been a bar since 1908. Its back bar, obtained through a Fitchburg Brewery promotion, was shipped around Cape Horn in 1913 from Belgium and is thought to date back to the 1850s.
The wood booths and paneled ceiling at House of Shields (39 New Montgomery, SF. 415-975-8651, www.houseofshields.com) have been there since 1908, when the watering hole first opened for business. A tunnel, left over from Prohibition, connects the place to Maxfield's. And the men's room has a urinal roughly the size of a refrigerator they don't seem to make 'em that big anymore.
Last year the Little Shamrock (807 Lincoln Way, SF. 415-661-0060), an Inner Sunset bar established in 1893, put up a sign reading, "We've been here for 113 years and our prices prove it!" It's true: a shot of Jameson goes for just four bucks at the cozy tavern. Its Victorian-era atmosphere, with broken velvet-upholstered parlor chairs and a potbellied stove in the dart room, will take you back in time.
Maxfield's (Palace Hotel, 2 New Montgomery, SF. 415-512-1111, www.maxfields-restaurant.com) is named for Maxwell Parrish, the artist of the vibrant realist depiction of a man and his flute hanging above the back of the bar since 1909. Back in 1875 it was called the Pied Piper, and in 1906 it was gutted by the fire, along with the rest of the Palace Hotel.