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 541 reviews
Beth_J, Jun 2026
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.
AubreyHill, Jun 2026
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.
Mitchell_C, Jun 2026
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.
TiEra_W, Jun 2026
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.
Jeanne_N, Jun 2026
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!
Anonymous, Jun 2026
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!
Nancy_E, Jun 2026
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.
David_A, May 2026
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!
Andy_M, Apr 2026
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.
Glen_W, Apr 2026
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.
Kayla_S, Oct 2025
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!
Karen_K, Oct 2025
Fabulous! We’d give a 10 star review if possible. Friendly, knowledgeable, and funny all in one description. Would recommend to anyone wanting a walkable tour of the great city of Portland Maine.
Response from Host, Oct 2025
That's very nice of you to say. Thank you! I love showing people around my hometown, so I'm happy to hear you liked the experience so much.
Karen_H, Oct 2025
Great — really good tour. Guide was great — his independent small company is an asset to Viator. Thks
Response from Host, Oct 2025
Thanks for the great review! I love taking about history with visitors and I appreciate you choosing this tour while you were here. I had a great time too.
Janet_G, Oct 2025
Excellent, informative tour. The tour guide was very knowledgeable of Portland history. There was a walk but with frequent stops which allowed for a bit of rest, or shade. He spoke clearly and loudly enough for all to hear and encouraged questions.
Response from Host, Oct 2025
Because Portland is such a walkable city, I've been able to design a tour route that includes lots of opportunities to stop and appreciate the landmarks. I'm glad you had such a great time! Thanks for the review.
Natalie_A, Oct 2025
Dugan was engaging, funny, and so informative about Portland's lesser known history. We learned a lot and he had great tips for greater exploration throughout Portland.
Response from Host, Oct 2025
I'm glad you appreciate the lesser known history and landmarks I highlight on this tour. I think it's important to offer credit where credit is due! Thanks for taking my tour and reviewing it.
Antonio_R, Oct 2025
Dugan was outstanding. A true local, afable, knowledgeable, funny and customer centric. We would strong recommend having him as a tour guide.
Response from Host, Oct 2025
Thank you for the recommendation! And for the compliments. Is very nice to hear. I hope you really enjoyed the rest of your time in Portland!
Angela_F, Oct 2025
We so enjoyed this tour! Dugan was a great guide: I don’t think anyone asked him a question that he couldn’t answer immediately and fluently. I greatly appreciated the thought and research that went into his presentations of stories and figures that are often otherwise ignored. I’d definitely recommend it!
Response from Host, Oct 2025
The ignored stuff is really important to me. I like to offer credit where credit is due, which sometimes means bringing up stories that rarely get talked about on walking tours. I'm glad you appreciate that too! Thank you very much for writing a review.
Matthew_M, Sep 2025
Very knowledgeable, friendly, and efficient. We likely only got to scratch the surface of this city’s history but Dugan was fantastic. Learned a lot!
Response from Host, Sep 2025
You're right about scratching the surface! There are so many stories from history that have largely been forgotten. Thank you for learning about some of them with me!
Ronald_T, Sep 2025
Excellent tour learning incredible information about the area and its history. Dugan our tour guide was funny while being informative
Response from Host, Sep 2025
Funny and informative is a great combination for a tour guide. I am honored you feel I have achieved that. Thanks for reviewing my tour!
Bernard_B, Sep 2025
Dugan was excellent. Very knowledgeable and moved at a good pace. Ends at the harbor which was also nice. Would recommend for sure.
Response from Host, Sep 2025
I'm glad you liked the pace! I like to provide guests with the ability to ask questions at every tour stop, but I also keep things moving so we get to see and talk about lots of different things. Thanks for reviewing.
Sharon_Q, Sep 2025
Our tour guide was amazing and very knowledgeable! I highly recommend this tour. I have done dozens of tours in many cities, he was one of the best!
Response from Host, Sep 2025
I'm honored to rank so highly in your experience with tour guides. Thank you for saying so! And thanks for choosing my tour of Portland.
Douglas_B, Sep 2025
Dugan, our guide, had excellent knowledge of the history of Portland and if he didn't immediately know the answer to a question, he quickly found the answer while walking to the next stop. Lots of interesting tidbits shared.
Response from Host, Sep 2025
I always encourage questions from guests so I can personalize my tours a bit. Thanks for bringing your curiosity! I loved meeting you and showing you around Portland.
Brett_A, Sep 2025
Two hours well spent in Portland. Tour guide was knowledgeable. Definitely focused on lesser known history facts.
Response from Host, Sep 2025
I like knowing that Portland's lesser known historic figures are getting the credit they're due. I'm glad you enjoyed the tour! Thanks for posting a review.
Janet_S, Sep 2025
f cobblestones could talk, they’d probably sound like our guide. Passionate, witty, and overflowing with stories that made centuries-old history feel like juicy gossip from yesterday. Instead of dry dates and dusty facts, we got duels, scandals, rebellions, and more than a few jokes that made me snort-laugh in public (sorry, pigeons).
This wasn’t just a walk — it was like stepping into a time machine, except with fewer risks of plague and more opportunities to grab good coffee along the way. Our guide clearly lives this history; every street corner came alive with tales of heroes, rogues, and questionable fashion choices from the past.
If you like your history with a side of humor and your education disguised as entertainment, this tour is a must. Just wear comfy shoes — because time travel is surprisingly hard on the feet.
Response from Host, Sep 2025
I guess the risk of plague is still pretty low compared to what it used to be. Thank you for journeying with me through the ages! I had a great time too.
Danielle_P, Sep 2025
The walking tour was a perfect pace and it combined history and fun places to eat! The reviews are spot on and he is an award winning tour guide!
Response from Host, Sep 2025
The focus of my tour is history, but I also provide guests with an overview of Portland by sharing a few anecdotes and pointing out a few modern phenomena like award-winning restaurants. I'm glad you really liked that format! Thanks for saying so.
Daniel_K, Aug 2025
We had an amazing experience on this walking tour of Portland, Maine! Our guide was knowledgeable, friendly, and shared so many fascinating stories about the city’s history, architecture, and local culture. The pace was perfect, and we discovered hidden spots we never would have found on our own. Highly recommend this tour to anyone looking to get a true feel for Portland!
Response from Host, Aug 2025
I'm happy to share Portland's hidden spots as well as its major landmarks with visitors. Thank you for taking the time to write out your review!
Elizabeth_M, Aug 2025
We participated in this tour while stopped in Portland on a cruise. We've never been fans of the cruise tours where you pile 40+ people on a bus with a canned presentation. Dugan's tour was very fun, informative and quite interactive. He is a very personable and animated tour leader. Highly recommend.
Response from Host, Aug 2025
I similarly am tired of mass tourism, which was a motivation for me to start offering tours as an independent guide. Thank you for finding my little business! And thanks for the review.
Rachelle_R, Aug 2025
Dugan was so knowledge about all the places we went to. We loved how he researched deeper than the surface to bring history and its relevance forward - especially the woman of Portlands past. Who would have known we were going to learn so much about crowd surfing, cowboys and corn as well as molasses and employee wellness programs! Highly recommend this tour.
Response from Host, Aug 2025
You know my specialty! Portland's past is full of surprises, especially when you're ready to dig a little extra to find those lesser-told stories. I see you're as impressed as I am with what I found in the archives! Thanks for taking my tour.
Heather_K, Aug 2025
Dugan is a wealth of knowledge and a pleasure to spend a couple hours with. He made history and architecture humorous and rememorable!
Response from Host, Aug 2025
A pleasure! That's very nice of you to say. I really enjoy telling stories and showing people around, so I'm glad you had a great time. Thanks for saying so in a review!
Michele_D, Aug 2025
This is a MUST DO experience. Our daughter had recommended it to us after she participated in this excursion as part of a bachelorette weekend! Dugan is a gifted orator and shares an abundance of knowledge regarding the history of Portland, Maine which spans over centuries. BTW—there are many surprises along the way as well!
Response from Host, Aug 2025
Thank you for the compliment! I've been honing my oration skills over the years, so it's validating to hear. Thank you for taking the tour and writing out this recommendation!
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