Underground Portland Walking Tour

Underground Portland Walking Tour

Experience the darker side of Portland's past and discover the real story behind the famous Shanghai Tunnels.

Portland wasn't always the poster child for livability and urban planning that it is today. On this leisurely stroll through the Old Town and Chinatown neighborhoods, your guests will hear the true story of Portland's rough-and-tumble past.

Not all of Portland's illicit, naughty, bawdy, corrupt, shady activities happened below street level, but all were "underground" and hidden from the public eye. You'll discover both the socially and the physically underground on this tour. This walk exposes the city's sordid side and is a treat for lovers of all things sinister – crime, scandal, and controversial characters abound. It's a no-holds-barred excursion into the worst Portland's past has to offer.

After touring streetside for three-fourths of the tour, we’ll hand out flashlights and venture into the subterranean under Old Town Pizza, in an area that once led to the legendary Shanghai Tunnels. If you want the true, inside story behind crimping (the real name of what is now called shanghaiing), you've come to the right place. Shanghaiing is what makes it to TV, but we'll surprise you with a fun and unscripted account of all of the other scandalous events from Portland's past.

This easy 1.5 mile walk is open to all ages and levels of athleticism. There is at least one set of stairs on the tour. Due to the nature of some of the topics covered we do not recommend it for very young children.

Minimum Tour Length: 2 hours

Featured Items of Interest...

Oregon Wine Country Coach Tour

Experience first-hand why experts consider the Willamette Valley one of the world’s great wine regions.

Alias and Alibi

Challenge your tour guests to a thrilling game where they solve a crime before it happens. It's James Bond meets Get Smart meets Clue with a little bit of CSI.


Guest badges can be a hassle, but they're easy for you when we process them.