Hidden Histories Walking Tour: Discover Portland

Explore the rich and diverse lives of Portlanders from various backgrounds and identities on a guided historical walking tour, immersing yourself in the Old Port, waterfront, and downtown district along the way

Cancellation: No refunds for canceled bookings.
Highlights
  • Step back in time as you walk along piers and wharves that were once managed by Black longshoremen, discovering their untold stories
  • Delight in the invigorating sea breeze as you take in panoramic views of the historic working waterfront, filled with tales of maritime industry
  • Listen to captivating narratives about the robber barons who amassed…
What's Included
  • Professional storyteller-historian as a guide
  • 2 hours of riveting narration
  • Donation toward restoring the Abyssinian Meeting House, America’s third-oldest standing Black church
Additional Information
  • Wear comfortable walking shoes.
  • Dress in layers and weather-appropriate clothing.
  • Bring an umbrella if there is a chance of rain; we rarely cancel.
  • Tour route is approximately 1.5 miles.
  • Tour ends 0.3 miles from starting location.
  • Pets are not allowed; medically-required service animals are welcome.
  • Route is wheelchair accessible.
Location
167 Middle St
Middle Street
Meet Dugan in Post Office Park at the corner of Exchange Street and Middle Street. He'll be standing amongst the small boulders and holding a sign that says "Portland by the Foot."
Cancellation Policy

You can cancel or rebook your reservation emailing [email protected] or by calling or texting 207-200-5885. If you give us more than 24 hours notice, we can offer a full refund or move your reservation to a different date. If you give us less than 24 hours notice, we cannot provide a refund or rebooking credit. In case we need to cancel on…

Customer Ratings
4.6
(1871 Ratings)
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Additional
May 20, 2026
Dugan‘s tour was engaging, fact-filled and fun.
Review provided by Peek Pro
Additional
May 18, 2026
Absolutely love Dugan’s dry sense of humor and deadpan delivery. Dugan has an incredible depth of knowledge and is able to relate it without coming off as entitled or arrogant. Dugan actively listens to questions during the tour and can pretty much answer any historical questions thrown his way. Very enjoyable tour.
Review provided by Peek Pro
Additional
May 14, 2026
Excellent and knowledgeable guide who provided a thoughtful explanation of each topic and provided humor and a few personal stories to keep the group engaged. He was able to provide answers to the many questions asked. Thank you for a great experience!
Review provided by Peek Pro
Additional
Apr 29, 2026
The guide was very knowledgeable about Portland history, I would definitely recommend doing a tour with Gunan.
Review provided by Peek Pro
Sabrina
Apr 20, 2026
Dugan was fantastic. It down poured torrentially during our tour, and he still made it fun and interesting. We learned a lot. Thank you!
Review provided by Peek Pro
June
Apr 18, 2026
Dugan was knowledgeable and passionate about all things related to Portland history and culture. He was extremely personable, engaging, and entertaining. So glad we saw a brochure at our bed and breakfast and decided to take this tour!
Review provided by Peek Pro
Additional
Apr 18, 2026
The tour was very different not your typical tour, it was very personable. We felt very comfortable with asking questions. Would definitely go again.
Review provided by Peek Pro
Additional
Apr 12, 2026
Portland by the Foot was an fun and informative tour. Dugan made it very interesting by showing historical pictures of current places
Review provided by Peek Pro
From $49
1 - General
Cancellation: No refunds for canceled bookings.