Local guide Dugan Murphy describes local history on Wharf Street to awed guests

$42 | 2 hours | 1.5 miles

Portland Hidden Histories Walking Tour

The inclusive and surprising overview of Portland history you’ve been looking for.

Eight people listen to guide holding a photograph of Black firefighter, William Wilberforce Ruby

Beyond mainstream history

We’ve combed through piles of archives to find the most intriguing — and too often untold — stories of people from all backgrounds and identities who have shaped Portland with wit and grit.

Both a fantastic historical overview of Portland, Maine, and an exploration into previously hidden stories, on this tour we’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk through centuries of destruction and revival into the present.

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.

Surrounded by cobblestones, guests in historic Boothby Square gazing at historic buildings representing four centuries of architecture

The best of Portland

With our fun and knowledgeable locally-raised guide, Dugan, you’ll have two hours to slow down and immerse yourself in the best Portland has to offer.

Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, on this tour you’ll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay.

Passing the colorful displays of welcoming, locally-owned boutiques, you’ll enjoy rich scents coming from award-winning restaurants, bakeries, and coffee shops, and may even catch a local musician’s tune floating on the wind from one of many lively parks!

You won’t know which to contemplate first: the stunning public art or which cocktail bar, brewery, or distillery you’ll visit later…

Don’t just visit Portland—
connect with the city!

Tour details

Price
$42 per person

Group size
15 people max

Duration
2 Hours

Neighborhoods visited
Portland's Old Port, waterfront, and downtown

Length & difficulty level of walk
1.5 easy miles of well-paced walking, including some opportunities to sit and catch the shade when sunny.

Participants will be asked to traverse some uneven sidewalks, walk up a staircase of 6 steps, and walk down two staircases (24 steps total).

Accessibility
✔️ Fully wheelchair and stroller accessible upon request

Starting location
Post Office Park at the corner of Middle and Exchange Streets - Open in Google Maps
(0.5 miles from the cruise ship terminal)

Ending location
Bell Buoy Park at 54 Commercial Street - Open in Google Maps
(0.3 miles from start; next door to the cruise ship terminal)

Tickets
✔️ Instant confirmation via email
✔️ No ticket needed to check in — simply give your name to your guide!

Included
✔️ Professional, locally-raised guide
✔️ Donation to the restoration fund of the Abyssinian Meeting House, America’s third-oldest standing Black church
🚣🏽 10% off Portland Paddle water tours (instructions at confirmation)

Not Included
❌ Gratuity for your guide

Cancellation
✔️ Free cancellation with a full refund up to 24 hours in advance
✔️ Tours are rain or shine! We very rarely cancel.

Important to Know
✔️
Arrive 10 minutes early
✔️ Plan ahead for parking, avoiding 2-hour street parking
✔️ Check the weather and dress in layers for comfort
❌ No bathrooms are available during the tour
❌ Animals are not allowed unless medically necessary

What to bring
✔️ Comfortable shoes, sunglasses, water, and perhaps a jacket or hat
✔️ Face mask in case we have the opportunity to tour a historical building
✔️ If it’s raining, bring rain gear and/or an umbrella

Walking tours designed for you

A city built for walking tours

Portland is a city best experienced on foot. Our walking tours allow you to truly appreciate the city’s many mysteries, which are easy to miss when driving by and impossible to see by car or bus.

Small groups

No jostling for the best spot or straining to hear on this tour! We limit groups to 15 guests so you can have the intimate experience you expect — with plenty of space for comfort and questions.

Gently paced

With an accessible path designed for folks with varying mobility needs, this is a gently paced tour appropriate for most people. Expect a moderate pace with 5-minutes or less walking at a time.

5-star guide

Visitors can’t say enough good things about our guide, Dugan. He’s a locally-raised historian and performer who has guided well over 29,000 happy guests through his hometown. Tripadvisor named him the top-rated tour guide in Maine!

For visitors and locals alike

We’re consistently rated five-stars by guests of all backgrounds — no matter if they are a tourist visiting for the first time, a local taking a stay-cation or hosting visitors, or groups looking for a one-of-a-kind experience.

Good for you, good for Portland

If you are looking to travel with the smallest carbon footprint, stay active, and support small businesses, this tour is for you!

  • The best tour I've ever been on! The content was accessible and thought-provoking, less like a history lesson in school, more like an engaging conversation with a friend.

    Sean O. | 2022

    ⭐⭐⭐⭐⭐
    Google Reviews

  • My only regret is that I did the tour on the last day I was in town — if I’d known how much fun it would be I would’ve booked his other two tours as well!

    Natalie G. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Even if you don't think you are into tours, do it. Dugan's tour allowed us to get a lay of the land, some history, and the opportunity to engage in fun, thought provoking conversations!

    Vonda L. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Dugan is an encyclopedia of knowledge and an entertaining and engaging story teller. This was history telling at its richest!

    Elizabeth G. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Dugan was animated and inclusive, covering the Irish, Black, Chinese and French populations who contributed to the rich history and economy of Portland. Really an enjoyable journey on a hot day!

    Ellen O. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Viator

  • I love that Dugan did a lot of research to give us insights that you wouldn’t necessarily get from a typical travel guide book or Wikipedia page. He also found old photos and took us to their locations!

    Explorer | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Best tour we took in Portland — interesting and thought provoking! Great easy walk with plenty of stops. Dugan has a deep knowledge of history that he shares with enthusiasm.

    Ello | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • I can honestly say that this was by far the most informative walking tour I’ve ever experienced. Dugan is a wealth of knowledge, and he makes history come alive!

    Elizabeth W. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Generally not a fan of walking, tours, or male-identified experts talking at me. And yet this tour was a delight! Dugan brings a humility to the history and a strong framework around histories hidden by oppressive structures.

    Jo | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

  • Just do it, you'll be glad you did!!! Our group was in Portland for meetings and we wanted to do a team-building activity that was out of the ordinary. Dugan didn't let us down!

    Paul B. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • The pace was relaxed and pleasant and I enjoyed the small group. It was obvious how well informed and excited about Portland history Dugan is. I highly recommend this tour!

    Kathy P. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • We are a family who tries to do the best tours in town when on vacation. Sometimes it’s a hit sometimes it’s a miss. This tour was a huge hit!

    Bailey K. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Dugan has great energy; the whole experience was very warm and friendly. Even though we live in Portland, we learned a ton about the political, social, economic, and architectural history of the city.

    Tucker B. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • This was a great walking tour. We got a good feel for this part of the city, learned a lot of interesting history with food for thought that is relevant in today's world. Dugan has so much to share and is super kind, insightful, thoughtful — and fun!

    Cheri K. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Highly recommend this knowledgeable, well-organized and engaging walking tour. Dugan is an excellent guide. ...Excellent restaurant recommendations too!

    Shaun H. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • We have been on many walking tours and this measured up to the best of them! Dugan had a very deep and well-researched understanding of Portland’s history but also had the ability to keep us engaged and entertained for the two-hour walk.

    Path | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • If you want a balanced history that covers the contributions of European, Native, Black and Asian populations, Dugan is your man!

    Durell C. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Dugan did an excellent job at acknowledging the more socially complicated aspects of the region’s and country’s history, and how they inform our understanding of the identity of American culture.

    Mitch | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Google Reviews

  • Using old photos and engravings, Dugan allowed us to glimpse the past and how it shaped Portland's present day. His personal anecdotes and humor were entertaining. I can't wait to join him on his other two tours!

    NY | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • As locals, my mom and I (82 and 58) were amazed at how much we learned. The tour is two hours long and makes a two-mile loop, but we never got tired. Dugan was careful to stop in shady spots!

    Heather P. | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • I loved this tour. I have lived in the Portland area for 40+ years and learned so many interesting details! I will now look at things differently when I'm in town! I can't wait to take the other tours.

    Relax | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • A treasure of a tour! The group ranged in age from children to grandparents and we all had a memorable experience! Great use of humor and wonderful depth in storytelling that left us hungry for more.

    Travel Light | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • I had an absolute blast on the Hidden Histories tour, which I consider to be an excellent introduction to the wonderful city of Portland. Dugan is clearly very passionate about the area and that shines through in his storytelling.

    Natalie G. | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

  • I was especially impressed by his inclusive approach—not only including the usual stories about the 'old white guys' who built Portland, but also the women and people of color who were historically important to the growth and evolution of the city.

    Elizabeth | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

  • I love that we hear about people you don’t necessarily hear about in conventional history books. The two hours went by quick, and there were plenty of opportunities to sit. Would highly recommend!

    Explorer | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

  • We had so much fun and the tour helped us learn where to eat, where to do things, and was informational about the actual city. Above all the tour guide was great with how he interacted with everybody and brought the whole group humor! 10/10 definitely recommend!

    Bailey | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

  • The topics were woven together with narrative coherence that made the tour engaging and easy to follow. As locals, we would definitely take out-of-town (or in-town) friends on this tour, and look forward to taking Dugan’s other tours!

    Tucker B. | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

  • Dugan encourages questions and it’s clear he’s done research with local historians — but he isn’t a dry and droning historian. His enthusiasm, entertaining anecdotes, and some solid Dad Jokes kept the tour lively and surprising.

    Heather | 2022

    ⭐⭐⭐⭐⭐
    Tripadvisor

Book with confidence

Excellent tour experience

Portland by the Foot is the top-rated tour company in Maine on Tripadvisor and consistently rated five-stars.

Free cancellations

Cancel up to 24 hours in advance for a full refund (48 hours for private tours). No trip insurance needed! We know that plans can change — that’s why we offer a generous cancellation policy.

Value for your money

Book directly on this website for the best price. If you get tickets elsewhere for more, let us know and we’ll re-book you at the lower rate!

Our tours regularly sell out!

To get your preferred tour time and to avoid missing out, we highly recommend booking as soon as possible.

FAQ

  • Highlights of the Hidden Histories Tour include: Commercial Street waterfront; Bell Buoy Park; United States Custom House; Custom House Wharf; Portland Pier; Mariner's Church; Boothby Square; Wharf Street; Foundry Lane; John Ford Statue; Wadsworth-Longfellow House; Monument Square; First Parish Church; Portland City Hall; Exchange Street; and Post Office Park.

    Oh, and plenty of boutiques, award-winning restaurants, museums, and more!

  • Advanced purchase is strongly recommended, as tours often sell out. To maximize your chances of getting the day and time you prefer, book well in advance.

  • Arrive 10 minutes prior to the start time to check in.

  • Portland is very walkable, so if you are staying on the peninsula, plan to walk! The tour starting location is a short walk from any accommodation on the peninsula.

    To skip the hassle of parking if you’re staying off-peninsula, catch a rideshare or taxi to the tour start location.

    If you do drive, plan to arrive early. Paid parking is available throughout Portland, but finding on-street parking can be time consuming and parking at a 2-hour meter means risking a ticket.

    Make parking easy and park in a garage. We recommend the Cumberland County Parking Garage at 192 Newbury Street, which is 3 blocks (a 3-minute walk) from the starting location.

  • We want all of our guests to have a fantastic and comfortable time and do our best to offer fully accessible tours.

    For questions about tour accessibility and how we can accommodate your specific needs, call 207-200-5885 or email hi@portlandbythefoot.com.

    Details about this tour that may be helpful:
    ✔️ The length of this tour is 1.5 miles.
    ✔️ There are opportunities to sit, but the majority of the time you’ll be traveling from place to place or stationary without the opportunity for a seat (unless you bring one!). The longest distance between tour stops is about 0.2 miles (a 4-minute walk).
    ✔️ We will travel at a moderate pace and Dugan will always wait until all group members are assembled at a stop before offering tour narration.
    ✔️ Portland’s streets and sidewalks run the gamut from A++ awesome to “Boo! One star!” If you use a wheelchair or a walker or are unsteady on your feet, you might experience mobility challenges on the tour as we traverse cobblestone streets, uneven brick sidewalks, and narrow pathways. If you have mobility needs, tell Dugan so he can modify the tour to more comfortable routes.
    ✔️ While there can be up to 33 stairs per tour, all tour routes can be modified to avoid stairs while visiting all landmarks. If you need to avoid stairs, notify Dugan.
    ✔️ We offer free admission to access providers. Call or text 207-200-5885 or email hi@portlandbythefoot.com to let us know they’re coming!
    ✔️ Service animals are welcome.
    ✔️ Bring a hat if you’re sun sensitive; Dugan will do his best to find shade, but success will depend on the time of day.
    ✔️ All tours are in spoken English, with some printed visuals. Dugan will speak loudly and clearly.

    Dugan is always open to feedback on the spot if needs arise on the tour.

  • Plan to use the bathroom prior to the tour; we won’t stop for a break during the walk. The closest public restroom is in Portland Public Library’s main branch in Monument Square; check their website for open hours. You can also check this list of public restrooms in Portland.

  • We love animals, but we cannot accommodate them on our tours unless the animal is medically required. We welcome guide dogs and other trained service animals.

  • Our walks involve about 2 hours of walking, standing, and talking. Some children may have a limited attention span; if that’s your child, this tour may not be a good choice for them.

  • We run tours rain or shine, canceling only when the conditions are extreme or dangerous.

    Portland is known for its sunny skies from June through October, and when it does rain, it’s typically either a constant sprinkle or a squall that passes quickly.

    Pack a light raincoat on rainy days and you won’t be sorry — take it from Kathleen, who visited in 2022 and expresses what we hear most from folks who take tours impacted by rain:

    “Although it was raining for most of our tour, I kept forgetting about the rain, while being entertained with Dugan’s engaging tales!”

    In the case of extreme or dangerous weather, we’ll cancel the tour with as much notice as possible. If we cancel, we’ll contact you directly to refund or rebook you.

  • Cancellation is free up to 24 hours in advance of your reservation time. Private tours may be canceled for free with up to 48 hours notice. We’ll rebook or refund you — your preference!

    To cancel or rebook, call or text 207-200-5885 or email hi@portlandbythefoot.com.

    If you book through a third party like Tripadvisor, Viator, or GetYourGuide, your reservation is subject to their cancellation and refund terms, which may differ from ours. Check your confirmation email for details.

  • To rebook, call or text 207-200-5885 or email hi@portlandbythefoot.com.

  • The tour meets at Post Office Park, which is 0.5 miles from the cruise ship terminal. It ends in Bell Buoy Park, which is next door to the cruise ship terminal.

  • If you feel your guide has provided a great experience, gratuities are encouraged — and welcomed — at the end of your tour. The standard tip in the industry is 20%.

  • We’re here to help! Call us at 207-200-5885.