Oregon: Portland's darker side

One of the hippest cities in the US, Portland wasn't always quite so forward thinking, as a dip into the seedier side of its past proves

By David Whitley
Published 7 Feb 2017, 08:00 GMT, Updated 8 Jul 2021, 11:35 BST

Portland Courthouse.

Photograph by Getty Images

"Men outnumbered women 16 to one," says Portland Walking Tours guide Conor. "And they were looking for the three Bs: beds, booze and beauties."

These days, Portland is a bastion of hipsterism, a city of microbrewers, coffee roasters, cyclists and locavores. But this is a fairly recent phenomenon. For much of its history, Portland has been a slightly seedy backwater. And it's that side of the city that the Underground Portland Walking Tour digs into with scarcely concealed relish.

Along 2nd Avenue, the city's main drag, Conor points to what was once Erickson's Saloon. "It was famous across the seven seas and took up an entire city block. There was a 700ft-long bar and it rented out rooms by the half-hour." No prizes for guessing the real occupation of the 'seamstresses' who frequented them.

Erickson's finally closed with the dawn of Prohibition, but that didn't stop others. By the Willamette River, Conor tells the tale of an enterprising landlady who ran a bar-cum-brothel on a houseboat. Back then, East Portland was a separate city, and every time the police from either side came to shut down her operation, she'd simply head over to the opposite bank. Eventually, the police got so annoyed that they cut her boat's anchor on the sly, causing it to drift towards the rapids. However, before it went over the edge, it was rescued by a friend — and patron — of the landlady and towed back into position. The next day, the police were baffled to see their nemesis was back.

The skulduggery wasn't just limited to bar owners. By the waterfront, there's Tom McCall Waterfront Park, named after the former Governor of Oregon, who implemented many progressive environmental policies but wasn't averse to a bit of conniving. The best story involves Vortex I, still the only state-sponsored rock festival in US history.

Fearing massive protests at the proposed Richard Nixon visit to Portland in 1970, McCall thought the best way to make sure hippy demonstrators didn't ruin the event was to stage the festival at the same time — at the foot of Mount Hood about 18 miles away — with free buses to get attendees there. Curiously, the advertised headliners — Jefferson Airplane and Santana — never showed up.

And, outside the courthouse, there's the spot where confiscated barrels of banned alcohol were ostentatiously smashed. When the building was due to be demolished, a discovery was made: holes in the ground atop a secret cellar where fresh barrels were kept. The booze would simply drain down into them, then get re-sold by the police on the sly.

The most notorious tunnels, however, were the Shanghai Tunnels, where, rumour has it, press-ganged sailors would be smuggled onto boats. As Conor takes us down to one, the truth is more mundane: they were used for the quick movement of goods, not people.

Not that 'Shanghai-ing' didn't happen. In fact, it was rife. In the late 19th century, 'crimps' would look out for fresh, illiterate arrivals from the Oregon Trail, loan them a couple of dollars and make them sign a contract, which stated the money wasn't a loan, but a pay advance that would have to be worked off. "Basically, you suddenly 'belonged' to a burly sea captain," says Conor.

Visitors are treated a little better these days, while 2nd Avenue is undergoing a renaissance. On the block where Erickson's Saloon once stood, I find no less than seven bars — all serving local craft beer.

Just two more of the Bs to go then…


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