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    5. Explore Weird & Wild Old Town Portland Walking Tour
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    Explore Weird & Wild Old Town Portland Walking Tour

    Walk downtown Portland for strange stories, hidden history, and a Voodoo Doughnut stop

    5.0 stars• 78 reviews
    From$41/ personincl. taxes and fees

    Duration

    2 Hours

    Includes

    Guide, stories, Voodoo Doughnuts

    Highlights

    Explore Portland’s weird and wild past on a 2-hour, 1.5-mile walking tour through Old Town and downtown. Follow your guide to historic landmarks, rooftop viewpoints, plazas, and story-filled corners.

    • Explore Old Town cobblestones and early Portland history
    • Hear Stories about the Shanghai Tunnels and floating bordellos
    • Learn Why Portland was nicknamed "Little Beirut"
    • Visit Voodoo Doughnuts for a classic Portland stop
    • Spot Murals, sculptures, and iconic downtown landmarks
    • Walk Past parks and green spaces, including the smallest park in America

    What's Included

    • Join A local, professional tour guide
    • Listen To stories of Portland’s famous and infamous characters
    • Visit The iconic Voodoo Doughnuts

    Things to know

    Recommended for guests ages 17+.

    Dress for the weather and bring a reusable water bottle if you can.

    Itinerary may change due to weather, closures, or traffic conditions.

    Cancellation Policy

    Full refund for cancellations made more than 30 days before your tour date. Bookings made or canceled within 30 days of the tour are non-refundable.

    FAQs

    Plan for ages 17+. Due to the nature of this tour, the operator recommends guests be at least 17 years old.

    Dress for the weather. Bring a reusable water bottle if you can; you can also use drinking fountains along the way.

    Yes. Expect restroom stops along the way, and let your guide know if you have an urgent need.

    Meeting details

    The Society Cafe, 203 NW 3rd Ave Suite 100, Portland, OR 97209

    Experience provided by Peak Tours and Transit, LLC
    Experience provided by Peak Tours and Transit, LLC

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #J2TA49

    Guest

    $41.34

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    78 reviews•Google Maps

    Peak Tours delivers consistently excellent Portland experiences thanks to their passionate guides, particularly Eric and Damon. Both come across as genuine Portland enthusiasts who bring the city's history and culture to life with engaging storytelling rather than dry facts. Guests repeatedly mention how knowledgeable these guides are, covering everything from historical developments to the current food scene, all delivered in an entertaining, accessible way. The tours strike a nice balance between riding and walking, with stops for photos and closer exploration at key spots. What really stands out is how personalized the experience feels, even in small groups. The guides adapt to guest interests, offer local recommendations, and create a relaxed atmosphere that makes the tours feel more like exploring with a friend than following a script. Several reviewers mention getting a solid overview that helped them decide where to spend more time later. Beyond city tours, they also handle waterfall excursions and private transportation for events, with that same attention to detail and flexibility that guests appreciate.

    What people are saying

    Review 1 of 5
    5/5

    Peak Tours now offers tours in Spanish, and I recently took the downtown tour. Our guide was authentic, passionate, and incredibly knowledgeable about Portland. As a local resident who has lived in Portland for over 30 years, I was amazed by the amount of new facts, fascinating details, and hidden gems I discovered along the way. Peak's guides also speak Portuguese, French, and English, which makes their tours even more impressive and accessible. I highly recommend this tour to both visitors and residents! Peak Tours is now offering tours in Spanish, and I recently took the downtown tour—it was extraordinary. Our guide was genuine, passionate, and incredibly knowledgeable about Portland. I highly recommend this tour to both visitors and locals alike!

    Photo of Kecia Welt

    Kecia Welt

    April 10, 2026

    Review 1 of 1
    5/5

    Peak Tours now offers tours in Spanish, and I recently took the downtown tour. Our guide was authentic, passionate, and incredibly knowledgeable about Portland. As a local resident who has lived in Portland for over 30 years, I was amazed by the amount of new facts, fascinating details, and hidden gems I discovered along the way. Peak's guides also speak Portuguese, French, and English, which makes their tours even more impressive and accessible. I highly recommend this tour to both visitors and residents! Peak Tours is now offering tours in Spanish, and I recently took the downtown tour—it was extraordinary. Our guide was genuine, passionate, and incredibly knowledgeable about Portland. I highly recommend this tour to both visitors and locals alike!

    Photo of Kecia Welt

    Kecia Welt

    April 10, 2026