Portland, Maine: Hidden Histories Guided Walking Tour
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 609 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Portland, Maine: Hidden Histories Guided Walking Tour worth booking?
Portland, Maine: Hidden Histories Guided Walking Tour is a 2-hour experience in Portland, United States, from $54 per person. It scores 92 out of 100 on the Outty Ranking, which we label “90+ Club”, based on a 5/5 rating across 609 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing. It sits in the Outty 90+ Club, the top tier of everything we rank.
- Outty Ranking
- 92 / 100
- Rating
- 5/5 (609)
- Duration
- 2 hours
- From
- $54 per person
Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising
What you get
About this experience
Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising stories largely left out of the history books. Get ready to broaden your sense of what Portland and Maine have been and could be. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, we'll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. We’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk together through the centuries. Enjoy an inclusive, empowering, and surprising constellation of tales that offers a welcome contrast to the more obvious themes you’re likely to experience on other tours. You'll enjoy 2 hours of narration over a 1.5-mile route with owner and guide, Dugan Murphy. He is Portland's top-rated guide on TripAdvisor!
What's included
Included
- 10% off water tours with Portland Paddle (instructions at confirmation)
- Two hour fully narrated guided tour.
- Donation toward restoring the Abyssinian Meeting House, America's third-oldest standing Black church
Not included
- A tip for your guide!
What you'll see and do
You and your guide Dugan will walk the downtown district, visiting major landmarks and a few hidden gems. Your guide Dugan will highlight unsung heroes and folks too often left out of the history books.
45 minutes here
Meet the woman who, a century ago, lived as her true self and improved the lives of Mainers around her, against all odds.
Pass by without stopping
Portland City Hall
Appreciate the architecture and hear the stories not captured in plaques and statues.
Pass by without stopping
The First Parish Portland Unitarian Universalist
Marvel at the resilience of Indigenous nations who survived colonialism and are skillfully navigating diplomatic relationships in the modern day.
Pass by without stopping
Our Lady of Victories (The Portland Soldiers and Sailors Monument)
Hidden stories are revealed about the folks not recognized by Portland's largest monument.
Pass by without stopping
The Wadsworth-Longfellow House
See the oldest building in downtown Portland and hear a surprising story about its world-famous inhabitant.
Pass by without stopping
Follow Dugan through Portland's Old Port, uncovering hidden histories of the city and her people. You'll learn about people from all backgrounds and identities whose grit and ingenuity made the city what it is today.
45 minutes here
John Ford Statue
Learn the complicated history of one of Portland's most famous sons.
Pass by without stopping
See beautiful Victorian buildings and learn about the largely forgotten history-makers who once inhabited them.
Pass by without stopping
Discover the often complicated relationship between stevedores, captains, shipowners, and common sailors in 19th-century Portland.
Pass by without stopping
Commercial Street
You and Dugan will stroll through the waterfront district along Commercial Street, discovering the people and economic forces that forged it. Get ready for an inclusive, empowering, and surprising constellation of tales that offers a welcome contrast to the more obvious themes you’re likely to experience on other tours.
30 minutes here
Learn what the other tours aren't telling you about the global implications of Portland's industrial and maritime histories.
Pass by without stopping
Custom House Wharf
See the picturesque working waterfront and discover the female figures who got left out of the history books.
Pass by without stopping
United States Custom House
Hear how changing federal policies have impacted life in this port city over the centuries.
Pass by without stopping
Where it starts and ends
Meeting point
Portland
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.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
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!
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Portland by the Foot
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- 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).
Photos
What travelers are saying
Outty’s summary of the themes that recur across 605 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
8 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
6 mentionsTravelers single out the guide as the reason the experience works.
Traveler reviews
605 verified traveler reviews for Portland, Maine: Hidden Histories Guided Walking Tour. Ratings and reviews provided by Viator and Tripadvisor.
Portland history walking tour
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 the operator: 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!
via Viator
Highly recommend
Outstanding tour. The guide Dugan was one of the best I have ever encountered in many tours—great knowledge of history, full of fun facts and surprises, readiness to answer any questions, spoke clearly and sufficiently loudly, kept us in shade and safe street crossings, good sense of humor, personable, friendly. I learned so much and had a fun time. I feel i know Portland a lot better.
Response from the operator: One of the best! Thank you so much. Aside from showing people around and sharing history, it is indeed important to find safe, comfortable spots to chat, and to make sure we are able to cross the street safely. Thanks for noticing!
via Tripadvisor
Dugan was fantastic. Top...
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 the operator: 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.
via Viator
Great history and a fantastic guide!
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 the operator: 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!
via Viator
A unique and interesting walk about Portland!
The tour was an impressive breadth of information and entertainment! Dugan’s curiosity about his home city and state…well, about everything, makes his tour unparalleled. He has us a timeline - easy - but added so much more. The ties to foreign policy, corn, gymnastics, Isiah and Chinese immigration, and women in Maine history kept us constantly engaged and excited to learn more. High praise and recommendations!
Response from the operator: For what seems to many a small, out-of-the-way city, Portland and it's history are full of remarkable surprises. I'm glad you're as impressed as I am by these connections! Thanks so much for writing a review.
via Tripadvisor
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 213
- Verdict
- 90+ Club
Why this scores 92
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Portland, Maine: Hidden Histories Guided Walking Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Portland.
How much does Portland, Maine: Hidden Histories Guided Walking Tour cost?
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Prices start at $54 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Portland usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Portland, Maine: Hidden Histories Guided Walking Tour take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Portland is not rushed.
Is Portland, Maine: Hidden Histories Guided Walking Tour worth it?
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It holds an Outty Ranking of 92 out of 100, which we label "90+ Club". That score blends traveler sentiment (5/5 across 609 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Portland, and how flexible the cancellation terms are. Scoring 90 or above puts it in the Outty 90+ Club, the top tier of everything we rank.
Can I cancel or reschedule Portland, Maine: Hidden Histories Guided Walking Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Portland, Maine: Hidden Histories Guided Walking Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Portland, Maine: Hidden Histories Guided Walking Tour?
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Around 213 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Portland can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Portland and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Portland, Maine: Hidden Histories Guided Walking Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Portland within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Portland?
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Portland sells lighthouse and lobster-boat tours in Casco Bay, Old Port food and brewery walks, seal and puffin cruises, and fall foliage runs up the Maine coast. On Outty we rank every Portland experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local, A Walk Through Time Tour in Portland, Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Portland?
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June to October, with peak foliage in early October. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Portland?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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