Explore history in the streets with Maine Historical Society & Portland by the Foot!
A portion of every tour ticket purchased here goes straight to MHS!
Guided walking tour topics
Black History
In the iconic Old Port, uncover Black history hidden all around you. You’ll trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality.
Maine’s earliest settlements couldn’t have existed without Black labor, skill, and insight — and since those first moments, Black Yankees have agitated and organized to resist indignity and realize power.
You'll meet the people who founded Maine communities, overturned slavery statewide, drove our maritime industries, swung elections, established houses of worship, rewrote the US Constitution, founded an African nation, crossed color boundaries, and expanded Mainers’ rights in the modern era.
Get ready for an impressive number of firsts on an international scale!
Starting location
First Parish Church at 425 Congress Street (head of Temple Street) - Open in Google Maps
Ending location
Eastern Cemetery at 228 Congress Street - Open in Google Maps
Neighborhoods visited
Old Port, waterfront, and East End
Hidden Histories
Both a fantastic historical overview of Portland, Maine, and an exploration into previously hidden stories, on this tour we’ll delve into intriguing — and too often untold — stories of people from all backgrounds and identities who have shaped Portland with wit and grit.
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.
I’ve combed through the archives and I’m excited to share what I’ve found with you!
Starting location
Post Office Park at the corner of Middle and Exchange Streets - Open in Google Maps
Ending location
Bell Buoy Park at 54 Commercial Street - Open in Google Maps
Neighborhoods visited
Old Port, waterfront, and downtown
We’re Best of the Best!
#1 in Portland & Maine, #2 in New England, #12 in USA
Portland by the Foot was selected for Tripadvisor’s Travelers’ Choice Best of the Best 2023! 🎉 This prestigious honor is based on high levels of above-and-beyond traveler reviews in the last year — fewer than 1% of 8 million experiences are awarded.
Tour details
Price
$49 per person
Group size
15 people max
Duration
2 Hours
Length & difficulty level of walk
1.5 easy miles of well-paced walking, including some opportunities to sit and catch the shade when sunny. The longest walk between stops is 0.3 miles (a 5-minute walk).
Accessibility
✔️ Participants may be asked to traverse some uneven sidewalks.
✔️ Fully wheelchair and stroller accessible.
Tickets
✔️ Instant confirmation via email
✔️ No ticket needed to check in — just tell me your name when we meet up!
Included
✔️ Professional, locally-raised guide
✔️ Donation to Maine Historical Society
🚣🏽 10% off Portland Paddle water tours (instructions at confirmation)
Not Included
❌ Optional gratuity for your guide
Cancellation
✔️ Free cancellation with a full refund up to 24 hours in advance
✔️ Tours run rain or shine! I very rarely cancel.
Important to Know
✔️ Check-in is 10 minutes before the tour’s scheduled start time
✔️ 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
✔️ If it’s raining, bring rain gear and/or an umbrella
I’m Dugan
And this is my tour company. I’m also the guide. I am a full-time public historian, the official tour partner of Maine Historical Society, a graduate of the Portland History Docent Program, and a recipient of the Dawnland – Maine Indian History Badge from the University of Maine. I’ve been a tour guide since 2018 and I relish creating personalized and delightful experiences for guests. Well over 34,000 people have enjoyed tours with me!
My Master’s in Community Planning and certificate in historic preservation inform my content, while my passion for Maine humor and storytelling informs my delivery. Aside from the nerdy history stuff, I also have a history of stage performance, sharing Maine humor and New England folk dance across North America.
This is Portland’s #1 top-rated tour!
Book with confidence
Excellent tour experience
Portland by the Foot is the top-rated tour operator in Portland on Tripadvisor and consistently rated five-stars!
Free cancellations
Cancel up to 24 hours in advance for a full refund. No trip insurance needed! I know that plans can change — that’s why I offer a generous cancellation policy.
Value for your money
Book directly on this website for the best price.
Get your tickets through this page and you’re supporting the work of Maine Historical Society!
Select a tour that works for you:
FAQ
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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.
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Highlights of the Black History Tour include: First Parish Church; Lobsterman Park; Exchange Street; Wharf Street, Mariner’s Church; Commercial Street waterfront; United States Custom House; Restaurant Row; India Street; Abyssinian Meeting House; Portland Observatory; Green Memorial AME Zion Church; Eastern Cemetery; North School; and Cathedral of the Immaculate Conception.
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First Parish Church at 425 Congress Street (head of Temple Street) - Open in Google Maps
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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.
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Post Office Park at the corner of Middle and Exchange Streets - Open in Google Maps
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Check-in is 10 minutes before the tour’s scheduled start time.
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Portland is very walkable, so if you are staying on the peninsula, plan to walk! The starting location for the tour 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’s starting 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. For the Hidden Histories Tour, I recommend the Temple Street Parking Garage at 11 Temple Street. For the Black History Tour, I recommend the Elm Street Parking Garage at 21 Elm St.
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I want all of my guests to have a fantastic and comfortable time, so I do my best to offer fully accessible tours.
For questions about tour accessibility and how I can accommodate your specific needs, call me (Dugan) at 207-200-5885 or email me at hi@portlandbythefoot.com.
Details about these tours that may be helpful:
✔️ The length of each 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 I will always wait until all guests 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 me so I can modify the tour to more comfortable routes.
✔️ I offer free admission to access providers. Call or text me (Dugan) at 207-200-5885 or email me at hi@portlandbythefoot.com to let me know they’re coming!
✔️ Service animals are welcome.
✔️ Bring a hat if you’re sun sensitive; I do my best to find shade, but success will depend on the time of day.
✔️ All tours are in spoken English, with some printed visuals. I speak loudly and clearly.
I am 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.
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I love animals, but cannot accommodate them on my tours unless the animal is medically required. I welcome guide dogs and other trained service animals.
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My tours 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.
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I 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.
In the case of extreme or dangerous weather, I’ll cancel the tour with as much notice as possible. If I cancel, I’ll contact you directly to refund or rebook you.
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Cancellation is free up to 24 hours in advance of your reservation time. I’ll rebook or refund you — your preference!
To cancel or rebook, call or text me (Dugan) at 207-200-5885 or email me at cancel@portlandbythefoot.com.
If you book through a third party like Tripadvisor, Viator, GetYourGuide, or Airbnb, your reservation is subject to their cancellation and refund terms, which may differ from mine. Check your confirmation email for details. -
To rebook, call or text me (Dugan) at 207-200-5885 or email me at hi@portlandbythefoot.com.
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Gratuities are optional and highly appreciated at the end of your tour. The standard tip in the industry is 20%.
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I’m here to help! Call or text me (Dugan) at 207-200-5885 or email me at hi@portlandbythefoot.com.
Commitment to anti-racism
I do my best to uncover and confront racist ideas that are embedded in the way I interpret the past and view my place in the present. I want the stories I share on Portland by the Foot tours to frankly reflect and challenge society's evolving system of unfair advantage based on perceived racial differences. I am committed to cultivating tour environments and business practices that counteract racism and other harmful historical patterns.
Land acknowledgement
We’re always calling this place Portland, but really it’s Machigonne. That’s the Algonquian name given to this peninsula by the Indigenous Wabanaki Nations who have lived here for more than 13,000 years. Despite encroachments by French and English colonizers and their descendant institutions, the Wabanaki have maintained their sovereignty and skillfully navigated diplomatic relations with the State of Maine and United States of America to this day. There are four federally recognized tribes in Maine today: the Houlton Band of Maliseet Indians, Penobscot Nation, Mi'kmaq Nation, and the Passamaquoddy Tribe.
As a guest in unceded territory, I am grateful for the Indigenous knowledge made available to me and for the ongoing stewardship of this land by the Wabanaki. I support these nations’ current claims to self-determination, land rights, water rights, fishing rights, hunting rights, ancestors’ remains, and historic artifacts. I urge the State of Maine and United States governments to recognize the jurisdiction and authority of Wabanaki regulatory powers over taxation, natural resources, land use, gaming, and trust land acquisition. I urge museums to repatriate to Wabanaki authorities all Indigenous human remains and sacred and funerary objects collected in Maine. And I commit to the ongoing process of decolonizing the stories I share with guests on my tours.
“These tours were a masterclass in conscientious historical storytelling” - Rachel C., July 2025
Portland by the Foot
Guided history walking tours of Portland, Maine
(207) 200-5885
hi@portlandbythefoot.com
Official tour partner of