Keep Portland Weird: A Walking Tour (Local Guide)

Discover Portland's storied past on a walking tour that explores its scandals, legends, and quirks. The perfect tour for those who like history with a wink, a shiver, and a dash of unexpected! This w

Discover Portland's storied past on a walking tour that explores its scandals, legends, and quirks. The perfect tour for those who like history with a wink, a shiver, and a dash of unexpected! This walking tour begins in Old Town, where we pull up the cobblestones to reveal the ghosts of rough-and-tumble early Portland. Once a lawless frontier outpost, the city was rife with scandal, from the infamous Shanghai Tunnels and floating bordellos to political intrigue and legends that grew as tall as the trees. Along the way, you’ll learn why Portland earned the nickname “Little Beirut,” how an Oregon governor once funded a rock festival, and how the city’s Naked Bike Ride became an unexpected symbol of protest and peace. We'll enjoy a stop for an iconic Voodoo Doughnut, a sweet taste of Portland’s weird side. Peak Tours is licensed and insured, local and family-owned, reliable and knowledgeable. We'd love to show you around!

From: $0.00

Location: Portland

What's Included

Community Discussion

Q&A

Q: Is this walking tour suitable for teenagers? My niece is 15 and loves history!

A: Absolutely! The Keep Portland Weird tour is great for all ages, including teens. The stories are engaging and often humorous, so your niece will likely enjoy the mix of history and quirky tales. Just keep in mind that some of the topics might be a bit edgy, but nothing too inappropriate. It's a fun way for her to learn about Portland!

Q: What should we wear for this walking tour? Is it casual or more dressy?

A: Casual is definitely the way to go! Comfortable shoes are a must since you’ll be walking quite a bit. Portland weather can be unpredictable, so maybe bring a light jacket or an umbrella just in case. You want to be relaxed and ready to enjoy those Voodoo Doughnuts!

Q: How flexible is the schedule for rescheduling this tour if something comes up?

A: The tour is pretty flexible! If you need to reschedule, just reach out to Peak Tours a couple of days in advance, and they’ll usually work with you to find a new time that fits. Just be aware that during busy seasons, it might be a bit harder to find spots, so plan ahead if you can!

Discussions

Just did the Keep Portland Weird tour, and it was epic!

I just got back from the Keep Portland Weird walking tour in Old Town, and wow, what a blast! The guide was super knowledgeable and had the best stories about the Shanghai Tunnels. Plus, we got to stop for Voodoo Doughnuts, which were insane. I went with my friends, and we really appreciated the mix of history and quirky facts—it was just the right amount of weird! Highly recommend it.

Thinking of gifting the Keep Portland Weird tour—any advice?

I’m considering getting the Keep Portland Weird tour for my partner’s birthday because they love history and all things weird about Portland. I’ve seen a few reviews, but just wanted to know if anyone has any tips or thoughts on the tour? Is there anything I should know about the meeting place or experience?