More than 100 years have passed since bands of hirsute men with a predilection for liquor and loose women first roamed the streets of Portland, but you could argue not much has changed since then, jokes guide Kevin-Michael Moore as we start our exploration of the city's historic downtown streets.

At the turn of last century, he explains, the riverside Oregon city was wild and lawless, thanks to its transient population of young men - hairy, as was the fashion of the time - who outnumbered women 16 to one. These days, facial hair and Portland hipsters go hand-in-hand; the city has carved out a reputation the world over for its craft beer scene, and has the dubious honour of housing more strip clubs per capita than anywhere else in the US. Beards, booze and broads still reign supreme in this uber-cool town in the Pacific Northwest of the United States, though it's a vastly different town today than the one of old.

Moore is taking our small group on a 90-minute Underground Portland Tour that promises to showcase the "worst Portland has to offer", exposing the sins of its murky past.

As one of the last surviving theater venues on Broadway, the Arlene Schnitzer Concert Hall. Photo / Getty Images
As one of the last surviving theater venues on Broadway, the Arlene Schnitzer Concert Hall. Photo / Getty Images

Walking backwards to chat to us as we move through the streets of Old Town, the actor-historian shares entertaining stories about the colourful characters who shaped Portland's past, and debunks many of the urban myths that haunt it to this day. The most notorious is the practice of "shanghaiing" - acquiring cargo ship crew by drugging men as they were drinking in saloons on bar stools sitting over trapdoors leading to the city's underground tunnel network, which ran down to the docks. Not true, says Moore, though the legal practice of "crimping" was common. This involved unscrupulous hoteliers offering rooms and liquor to penniless patrons, then tricking them into signing contracts they probably couldn't even read to repay bills that essentially sold them as slaves to boat captains for years of service.


The tunnels certainly existed, built to drain basements after the Willamette River flooded in 1894, and later expanded to create an underground transport network for merchants moving goods from the ships. Don't be sucked in by charlatans passing basements off as tunnels, Moore cautions - if you look up and see floorboards you're not in a tunnel.

Moore also tells us about the geography and history of the areas we're walking through, such as about the seven-block heart of Third Ave known as Nihonmachi (Japantown) before World War II when it was occupied by 3000 Japanese people. Not long after the Pearl Harbour attack in Hawaii in 1941 the community was driven out of town as anti-Japanese sentiment ran hot.

We learn about boarding-house owner Big Jim Turk, who crimped his son after they had a big fight on his 16th birthday, and about Nancy Boggs' Floating Palace of Sin - a houseboat bordello operated in the middle of the Willamette to evade paying tax to the corrupt police department of the time. Best of all is the yarn about August Erickson who ran one of the most notorious bars in town, Erickson Saloon, which people would come from all over the United States to drink at.

It had nine bars with troughs attached so men could pee where they were standing, and dancing ladies behind electrified chicken wire fences.

Things have moved on in spades since the chicken wire. A loose interpretation of the broad freedom of speech law in Oregon has allowed for masses of strip clubs to operate in Portland, and they range from heavy metal-themed venues to vegan clubs and steakhouses.

Our tour comes to a close where it began, back at the historic Merchant Hotel to have a look at one of its three tunnel entrances, off what was once a basement opium den.

The entrance is now sealed up with small slabs of concrete and there's no way to get in; even if there was you wouldn't want to - the top layers of the tunnels lie about a brick-and-a-half under street level. This may have been fine in the horse and buggy days, but is not particularly safe in modern times.

Nonsense some of it may be, but the alternative history of Portland's seedy underbelly is as entertaining as the reality.

One of Portland's famous food trucks.
One of Portland's famous food trucks.


Getting there

Hawaiian Airlines

flies daily from Auckland to Portland, via their hub in Honolulu. Economy Class return tickets start from $1779.

The Underground Portland Tour departs three times daily at 11am, 2pm and 5pm from 131 NW 2nd Ave, and costs US$23.