$49 | 2 hours | 1.5 miles
Portland Hidden Histories Walking Tour
The inclusive and surprising overview of Portland history you’ve been looking for.
Beyond mainstream history
I’ve combed through the 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.
The best of Portland
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
$49 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 miles (about 3,000 steps) of well-paced walking, mostly in the shade when sunny.
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).
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 — just tell me your name when we meet up!
Included
✔️ Professional, locally-raised guide
✔️ Donation to the restoration fund of the Abyssinian Meeting House, the third-oldest Black church still standing in the US
🚣🏽 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
Walking tours designed for you
A city built for walking tours
Portland is a city best experienced on foot. My 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! I 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 less than 5 minutes walking at a time.
5-star guide
I’m a locally-raised historian and performer and I’ve guided well over 34,000 happy guests through my hometown. In 2023, Tripadvisor named me the 12th-best tour guide in the US! Check out the reviews to see what guests are saying.
Trusted public historian
I am a certified Portland History Docent, holder of the University of Maine Dawnland – Maine Indian History Badge, and Maine Historical Society’s only official tour partner. Expect a history-rich and BS-free experience!
Good for you, good for Portland
If you are looking to travel with the smallest carbon footprint, stay active, and support small, independent businesses, this tour is for you!
Book with confidence
Excellent tour experience
Portland by the Foot is the top-rated tour company 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 plans can change — that’s why I offer a generous cancellation policy.
Value for your money
Book directly with me on this website for the best price. If you get tickets elsewhere for more, let me know and I’ll re-book you at the lower rate!
My tours regularly sell out!
To get your preferred tour time and to avoid missing out, I highly recommend booking as soon as possible.
FAQ
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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; Press Hotel; Exchange Street; and Post Office Park.
Oh, and plenty of boutiques, award-winning restaurants, museums, and more!
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My tours often sell out. To maximize your chances of getting the day and time you prefer, I highly recommend booking well in advance.
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Arrive 10 minutes prior to the start time to check in with me.
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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. I recommend the Temple Street Parking Garage at 11 Temple Street, which is 2 blocks (a 4-minute walk) from the starting location.
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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 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 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.
✔️ While there can be up to 33 stairs per tour, I can modify all tour routes to avoid stairs while visiting all landmarks. If you need to avoid stairs, just tell me when we meet.
✔️ 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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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.
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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.