Portland, Maine: Hidden Histories Guided Walking Tour
Recommended by 100% of travelers
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Portland, USA
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
With this small-group walking tour, you'll go beyond lobsters and lighthouses and get a look at the true Portland, Maine—across 400 years of history. Meander downtown and the Old Port, visiting hidden landmarks and learning about Wabanaki leaders and other people and events left out of the history books. Discover centuries of destruction, revival, underrepresented perspectives, and other elements that mainstream tours gloss over.
- Travel across Portland's hidden history, getting a rare look at the city
- Your local guide offers wild facts, city recommendations, and more
- Easy meetup with your guide at Post Office Park
- Get a fun, small-group experience on this limited tour
What's Included
- Two hour fully narrated guided tour.
- Donation toward restoring the Abyssinian Meeting House, America's third-oldest standing Black church
- 10% off water tours with Portland Paddle (instructions at confirmation)
- A tip for your guide!
Meeting and Pickup
Meeting point
- Post Office Park167 Middle St, Portland, ME 04101, USA
Meet at the corner of Middle and Exchange Streets by the small boulders in the park. Your guide will be holding a sign that says "Portland by the Foot." Check-in time is 10 minutes prior to the scheduled tour time. The park is one half mile from the cruise ship terminal.
End point
- Bell Buoy Park54 Commercial St, Portland, ME 04101, USA
Bell Buoy Park is on Commercial Street at the Casco Bay Lines ferry terminal. If you need to head back to where we started, it's only 0.3 miles (6-minute walk) away. It's also next door to the cruise ship terminal. Or sit a while to enjoy the ocean views!
Itinerary
1
Downtown
45 minutes • Admission Ticket Free
The Press Hotel, Autograph Collection (Pass By)
Portland City Hall (Pass By)
The First Parish Portland Unitarian Universalist (Pass By)
Our Lady of Victories (The Portland Soldiers and Sailors Monument) (Pass By)
The Wadsworth-Longfellow House (Pass By)
2
Old Port
45 minutes • Admission Ticket Free
John Ford Statue (Pass By)
Exchange Street (Pass By)
Mariner's Church Banquet Center (Pass By)
3
Commercial Street
30 minutes • Admission Ticket Free
Wharf Street (Pass By)
Custom House Wharf (Pass By)
United States Custom House (Pass By)
Additional Info
- Confirmation will be received at time of booking
- Wheelchair accessible
- Stroller accessible
- Service animals allowed
- Near public transportation
- Transportation is wheelchair accessible
- Surfaces are wheelchair accessible
- No heart problems or other serious medical conditions
- Most travelers can participate
- Pets are not allowed on tours unless medically required.
- Portland is a hilly city. Participants will walk uphill sometimes, along some cobblestones, up a staircase of 6 steps, and down two staircases (24 steps total).
- This tour/activity will have a maximum of 15 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
5.0
based on 624 reviews
Sort by: Most insightful
The guide Dugan is very knowledgeable. His presentationwas very well prepared and organized in different themes, interesting too. He was ready to answer Qs and was always encouraging people to bring them on. In general, it was a very much enjoyable tour.
Response from Host, Sep 2026
Thanks for bringing questions! I do always encourage them from guests. I want to make sure everything makes sense and that folks have an opportunity to sell more information about the topics that interest them most. I appreciate you taking the time to write a review!
Dugan the guide was amazing. He certainly knows the history of Portland Maine. Would strongly recommend this tour.
Response from Host, Sep 2026
I have certainly learned a lot about Portland, having grown up around here, plus doing a lot of research. I'm excited to share with guests. Thanks for taking a tour with me!
Dugan knows Portland and has so much historical knowledge but also makes the tour fun! I would recommend it!
Response from Host, Sep 2026
Thank you for recommending my tour! I had a lot of fun too. I'm glad you came.
Dugan was excellent! He was high energy, fun and extremely knowledgeable! We learned a ton about Portland that we would never have guessed. We highly recommend this tour!
Response from Host, Sep 2026
Even locals don't know much of the history we get into in this tour. Hence the name: Hidden Histories! I'm happy to have met someone else who finds these topics just as interesting. Thanks so much for reviewing your experience!
We really enjoyed our tour with Dugan. He is inclusive, welcoming, is genuinely very passionate about the history of Portland, and clearly loves the city! Highly recommend this tour to everyone looking to gain an appreciation about the history of the Portland, and hear interesting stories and anecdotes throughout the walk.
Response from Host, Sep 2026
I do love Portland. I feel lucky to have grown up here. Thanks for visiting and for choosing my tour while you were here! I'm glad you liked it so much.
Dugan was a very knowledgeable and passionate tour guide! This tour was a perfect overview of the history of Portland with some quirky, fun facts sprinkled in. Highly recommended!
Response from Host, Sep 2026
Thank you for the compliments! I'm glad you liked my tour so much. Thank you for choosing it!
We recommend! Dugan was very knowledgeable and entertaining. We learned a lot about the city. Especially enjoyed going into all faith meeting hall and seeing a real historic cannonball!
Response from Host, Aug 2026
Thank you taking a tour with me! I'm glad you had such a great time. I certainly did. Thank you also for the review!
Dugan was fantastic. Top notch guide. Extremely knowledgeable about Portland in addition to being funny and a great speaker. We could all keep up and hear everything he had to tell us!
Response from Host, Aug 2026
Those are all nice things. Thanks for saying so! I love telling stories and sharing history and I'm honored you feel I did such a great job.
Dugan is very knowledgeable and loves Portland history. He speaks clearly and is easy to hear and understand. He is also very entertaining!
Response from Host, Aug 2026
Thanks for recognizing that! A guide's ability to annunciate and project their voice is one of those things you tend not to notice unless it goes poorly. I'm glad you feel I did a great job!
Dugan was an amazing tour guide. His knowledge of the history of Portland was incredible. He made the tour. I would do t his tour again
Response from Host, Aug 2026
Thanks for joining me! I hope to see you another time either on this tour or on the Portland Black History Tour. Until then!
Great tour, one of the best walking tours I’ve ever been on. Dugan is knowledgeable, engaging and funny. He made Portland past and present come alive.
Response from Host, Aug 2026
One of the best! I'm honored. Thank you for taking a tour with me and for taking the time to post a review.
Our group of ladies absolutely loved this Walking tour. It was informative and he was hilarious! He made the city of Portland come alive.
Response from Host, Aug 2026
I loved meeting you all last weekend. You had great questions and I had a blast showing you all of Portland's underappreciated landmarks. Thanks for including my tour on your visit to Portland and for writing a review!
This tour is a great opportunity to learn the history of Portland. Duggan does an excellent job of sharing interesting details.
Response from Host, Aug 2026
Thanks for the great review! I had a great time showing you around. Thanks for choosing my tour of Portland!
A fun entertaining tour of Portland Maine. The guide Dugan is very knowledgeable clearly an enthusiastic historian. Enjoyed his presentation during our tour. Lots of fun.
Response from Host, Aug 2026
I do like history and I do love my job. There's just so much to share with guests! Thanks for choosing my tour and for taking the time to review your experience.
Dugan was an outstanding tour guide—informative, entertaining, and incredibly knowledgeable. He shared fascinating stories and historical insights in a way that kept the entire tour engaging from start to finish. It was a great experience, and I would highly recommend this tour to anyone visiting the area.
Response from Host, Aug 2026
There's so much history in Portland, so I like to take people to the most interesting landmarks and share the most relevant and surprising stories. I'm glad you liked the experience so much! Thanks for saying so.
Great tour! Very informative! Tour guide was very knowledgeable and funny! Would do this tour again.
Response from Host, Aug 2026
Thanks for the great review! If you do take the Hidden Histories Tour again, I look forward to seeing you then. I hope the rest of your stay in Portland went just as well!
Dugan was excellent!!!!! Fascinating facts and easy walk. Had lots of wonderful suggestions and fun dad jokes. I would highly recommend!!!!!
Response from Host, Aug 2026
I'm glad you liked my dad jokes. As you know, I really like to focus on history, but I also point out the humor now and again. Thanks for reviewing your experience!
Dugan was a great tour guide. So knowledgeable and also funny. We live in Portland and we learned a lot! So glad we decided to do the tourist thing today. Highly recommend!
Response from Host, Jul 2026
It was nice to have a few locals on the tour yesterday. Thanks for coming out! I also appreciate you taking the time to write a review.
Dugan was a fantastic guide to Portland history. He is approachable and fun and really knows the history of Portland deeply. He is also conscientious about finding shade when it’s hot and being aware of surroundings. Highly recommend his tour to orient yourself to Portland.
Response from Host, Jul 2026
A good tour guide is not only well read and good at storytelling, but also a person who knows how to keep people comfortable whole walking around outside. I'm glad you feel I achieved that! Thanks for saying so.
Good walking tour. Our guide was entertaining and knew what he was talking about. Able to answer lots of questions on the fly.
Response from Host, Jun 2026
Thank you for bringing your curiosity! I do love getting questions from guests. I appreciate you taking the time to review the tour.
The walk is long but the pace is easy and the guide is deeply knowledgeable. Basically any question you might have he probably has an answer to. He's also very willing to give you more info about whatever piques your interest. The bit that goes inside the First Parish was especially cool.
Response from Host, Jun 2026
I always invite questions from guests. It keeps the experience interactive and engaging while allowing me to personalize each tour. I'm glad you liked the tour so much! Thanks for saying so.
Wonderful tour and excellent tour guide. The tour provides a different perspective on the city that includes all citizens.
Response from Host, Jun 2026
That is important to me: including a broad swath of different people in the histories I present on this tour. I'm glad you find that important too! Thanks for choosing this tour while you were in Portland.
This was such a great tour. We got lucky and it was a small group of 6. Dugan arrived right on time and got us started. He was very friendly and once he realized where we were all from he added bits of historical context that connected to all of us. Dugan is extremely knowledgeable about the history of Portland and very nice. I highly recommend doing this tour if you can!
Response from Host, Jun 2026
I mostly talk about Portland, of course, but I also like getting to know my guests a bit, and talking with then about where they're from. I love being curious people! Thank you for choosing my tour and for leaving a review.
We had a very informative tour of the city of Portland. Dugan was very passionate about his city and was able to answer all of our questions about Portland and provide us with details of the city’s history from the indigenous peoples’ time to the present. As the city had burned several times, his showing pictures and actual places brought all of the history to life.
Response from Host, Jun 2026
And as you now know from the tour, the story of the Indigenous nations here is both the oldest and most current topic discussed. I'm happy to know you appreciated learning about them and other figures in the city's history. Thanks for joining me!
This walking tour is a great way to learn about Portland, Maine. Dugan is well informed, friendly, and funny. The tour took a little more than 2 hours, but the pace was reasonable, (definitely wear sneakers or comfortable walking shoes), and Dugan provides visuals from the prior events he discusses to help orient and explain what one is seeing in the present. The meeting park on Middle Street is easy to find, and I recommend arriving at least 30 minutes to the area around the park to ensure that you can find a parking garage spot and then walk to the meeting point. Dugan's knowledge makes it fun to ask questions as he knows or can find the answer. Also, as he is from the area, he can provide tips on things to do, and he recommended a lovely driving tour that allowed me to experience the lovely homes and scenery of the smaller picturesque towns of Maine. Overall, I would highly recommend Dugan and this walking tour.
Response from Host, Jun 2026
Thank you so much for the detailed review! And I'm glad you enjoyed visiting the smaller towns in Midcoast Maine after leaving Portland. Thanks for choosing my tour while you were here!
Dugan is one of the best tour guides that exist. He’s fun, knowledgeable and very interactive. I highly recommend taking his tour!
Response from Host, Jun 2026
One of the best! That's very nice to hear. Thank you for saying so. I appreciate you taking the time to review your experience on my tour.
Well worth the time and investment. Dugan’s dry humor and deadpan delivery were very entertaining. Extremely knowledgeable and is able able to relate without seeming arrogant. Would highly recommend (especially to Dropkick Murphy fans).
Response from Host, May 2026
These are some very nice compliments and I really appreciate you taking the time to write them out. I also appreciate an arrogance-free presentation. I'm glad that was your experience with me!
This walking tour was one of the best we have ever experienced, because of Dugan, our terrific guide. He is incredibly knowledgeable about the history of the community, and he includes a lot of fun tidbits that keep all the history from becoming overwhelming. We appreciated that Dugan is very sensitive about the many complicated dimensions of history in Portland. In addition, he was very open to all kinds of questions from us about not only the tour but also about enjoying our stay in Portland.
Response from Host, Apr 2026
One of the best! Thank you for the compliments. I love hearing guests' questions and I appreciate you bringing some.
Dugan was the best—engaged, engaging, enthusiastic, funny, and remarkably well versed in the history of Portland. I couldn’t imagine a more capable guide.
Response from Host, Apr 2026
Aww, that's very nice to hear. Thank you! I just love talking about history with visitors. And I love showing people around my hometown.
Unfortunately I was unable to make to the tour due to immigration check in from the cruise. Unable to reschedule or obtain a refund. Tour guide did try to get me on your even late.
Response from Host, Oct 2025
I'm sorry you weren't able to experience my tour! You let me know about 90 minutes beforehand that you would be participating in another shore activity that conflicted with this reservation. On your request, I kept in touch with you during the tour so you could join in late once your other Portland tour was over. You let me know about an hour into this tour that you wouldn't be able to make it after all. Unfortunately, Viator doesn't provide refunds for cancellations received after a tour starts. I hope the rest of your Portland visit and your cruise went well!
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