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 (about 3,000 steps) 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!

Trusted public historian

We are the official tour partner of Maine Historical Society, the definitive authority on our state's historical legacy. These tours are history-rich and BS-free... not to mention really entertaining! Welcome, Grade-A nerds and curious 12-year-olds.

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!

  • I frequently do walking tours of cities and Dugan’s tour is by far one of the best if not the best.

    Sandy B. | Apr 2024

    ⭐️⭐️⭐️⭐️⭐️
    Googe Reviews

  • So this tour was way above average and I don’t say that lightly and I don’t leave a lot of reviews (unless it is really special).

    Dave M. | Oct 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • The tour started on time, it was a congenial atmosphere where questions were encouraged, and it ended with everyone in the group saying this was a fantastic experience.

    Samantha T | June 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • The history tour that's not just about old white dudes!

    Christine M | Nov 2023

    ⭐️⭐️⭐️⭐️⭐️

    Viator

  • Dugan gives a great tour. He was so good we booked a 2nd tour on the same day because the first was so good!

    Marie R. | Sep 2023

    ⭐️⭐️⭐️⭐️⭐️

    Google Reviews

  • As a high school American history teacher, I can guarantee that any history buff will enjoy this tour.

    Cindy H. | Sep 2023

    ⭐️⭐️⭐️⭐️⭐️

    Google Reviews

  • Dugan is an amazing guide because he's a Portland native who is a super nerd when it comes to Portland's history, urban planning, economic growth, and research. Perfect length of time. Dugan is engaging and always happy to answer questions.

    Francesca B. | July 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • 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

  • 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

  • Dugan’s a local, public school inspired, passionate history buff with the timing of a professional comedian. Super fun!

    Kristen M. | July 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • We have been on many walking tours and this measured up to the best of them!

    Path | 2022

    ⭐️⭐️⭐️⭐️⭐️
    Tripadvisor

  • Dugan was a pleasure to chat with during the tour. I loved the fact that women and immigrants were featured in the stories, not afterthoughts.

    RJ Salem | Aug 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • What an awesome experience! He gives you a taste of the town from it's early days right up to it's current happenings, including perspectives of Native Americans, immigrants and women who have shaped the town.

    Duke V. | Oct 2023

    ⭐️⭐️⭐️⭐️⭐️

    Google Reviews

  • Dugan is a gentleman and a scholar (truly). He’s really skilled at building community within the tour group as well, a rare gift. Curious, honest, funny.

    Mary Ellen P. | Aug 2023

    ⭐️⭐️⭐️⭐️⭐️

    Google Reviews

  • 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

  • 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

  • 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

  • Dugan did an amazing job showing us hidden corners of Portland. He also shared stories highlighting the lesser known contributions of the local black and indigenous peoples to the city's history, which were incredible to hear.

    Andrew L. | Aug 2023

    ⭐️⭐️⭐️⭐️⭐️

    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 made it so much fun with lots of laughs and interaction.

    Satisfiedplusone | Aug 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • Dugan is knowledgeable and friendly guide. He loves the city and made us look at Portland in a very special way. Even pouring rain did not spoil the tour.

    Irene R. | July 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • We enjoyed the "Hidden Histories" tour so much that we immediately signed up for a different tour in the afternoon. Highly recommended!

    Steve W. | May 2023

    ⭐️⭐️⭐️⭐️⭐️

    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

  • Dugan is interesting, funny and most of all invested. He knows so much about Portland and conveys it with an enthusiasm and love that is contagious.

    Alan C. | Apr 2023

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • Dugan has the unique ability to hold one’s attention during his presentations. His personality, method of speaking to a group, and even his voice itself invites you to listen to what he is saying. Not everyone has this quality of holding people in their hands and entertaining them while they learn.

    Brusek | Oct 2022

    ⭐️⭐️⭐️⭐️⭐️

    Tripadvisor

  • The day we booked tour it was chilly and pouring and I have to admit, I did not want to go, but I'm so glad that we did! Dugan keep my mind off my cold & wet feet for 2 hours with the interesting history of Portland.

    KK78 | Oct 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.