GetYourGuide uses cookies to give you the best possible service. If you continue browsing, you agree to the use of cookies. More details can be found in our privacy policy.

See gallery
Experience the bad side of Portland on a guided walk. Learn about all the terrible, horrible, no good, very bad, seedy, seamy, and sinful things of the city’s past – and present. Head into the physical underground and learn about the Shanghai Tunnels.
About this activity
Duration 2 hours
Printed or mobile voucher accepted
Instant confirmation
Live tour guide
Free cancellation up to 24 hours before activity starts

Select participants and date:



  • Take a walk through Portland's subterranean past, and learn the truth about the Shanghai Tunnels
  • Experience the remains of the city’s physical underground
  • Delve into Portland’s shameful past of sex and ethnic crimes, gambling, and corruption
Full description
The sins of Portland's past are exposed on this tour of Old Town and Chinatown. You’ll walk through the remains of the city’s physical underground and learn about the underground subcultures of the city's sordid history.

This 2-hour guided walk is a treat for lovers of all things sinister and is a no-holds-barred excursion into the worst Portland has to offer.

The tour has been recently revamped to include a recently excavated subterranean area and new investigations into the worst of the illicit, naughty, bawdy, corrupt, and shady activities of Portland's past.

After you’ve walked along the city’s streets for the first part of the tour you’ll get a flashlight and head under the historic Merchant Hotel. This area once led to the legendary Shanghai Tunnels. If you want to discover the true story behind what is now called shanghaiing, you've come to the right place!

Your guide will also take you to dozens of other somber monuments of Portland’s shameful past of sex, ethnic crimes, gambling, corruption, and more.
  • Guided walking tour

Prepare for the activity

Meeting point

Meet your tour group from inside the Merchant Hotel at 131 NW 2nd Ave.

Open in Google Maps ⟶
Important information
Know before you go
Please dress for the Oregon weather as most of this tour is above ground and streetside. Comfortable walking shoes are recommended. Tours operate on time, rain or shine!
Customer reviews
Overall rating
4.4 / 5
based on 307 reviews
Review summary
Value for money

Organized by

Portland Walking Tours

Product ID: 37829