Portland’s Old Port Walking Tour
Wander the cobblestone streets on this self-guided audio tour
What to Expect
Portland’s Old Port may look like a bustling district of shops and restaurants, but its streets hold stories of sailors, reformers, and immigrants who shaped the city. This self-guided walking tour leads you through cobblestone alleys, merchant blocks, and landmarks tied to the Portland Freedom Trail, honoring the fight for freedom and civil rights in Maine. Along the way, you’ll discover how resilience, the sea, and a spirit of reform left their mark on the Old Port. More than a destination, this is a living story still unfolding.
Ready to go? Book below or download our app and purchase directly from your phone.
📍 Location: Portland, ME
🚶♂️ Type: Walking tour
⏱ Duration: Approx. 1hr 30min (flexible)
✅ Includes: App download, GPS-triggered audio, No expiration
📶 Works Offline: Download ahead of time - no cell service required
🎧 Multiple Languages: English, Spanish
Get Ready for Your Portland Self-Guided Tour
Explore Portland’s Old Port, a waterfront neighborhood where worn cobblestones and weathered brick tell stories of resilience, reform, and life at sea.
This self-guided walking tour takes you past the lively shops and restaurants to reveal the deeper history shaped by sailors, traders, immigrants, and social reformers.
As you move through the district, you’ll learn about the rebuilding after the Great Fire of 1866, follow key stops along the Portland Freedom Trail, and uncover the city’s complex connections to temperance, Prohibition, and maritime commerce.
From massive granite warehouses to working piers along Casco Bay, each stop reveals how endurance and adaptation define this place.
What sets this walk apart is its balance of mood and meaning. You’re not just observing the Old Port—you’re stepping into an ongoing narrative.
Portland’s past lives in its streetscapes, still active and evolving with every passing tide.
What You’ll See on Your Portland Walking Tour
Moulton Street
This narrow, stone-paved lane winds through the Old Port past buildings once central to Portland’s trading economy. It also forms part of the Portland Freedom Trail.
Post Office Park
Now a small shaded green space, this park sits on the former site of a 19th-century marble post office and serves as a quiet community gathering spot.
Tommy’s Park
Just across Exchange Street, this pocket plaza offers benches, trees, and mural views—a peaceful break from the bustle of the waterfront.
Casco Bay Lines
The main ferry terminal for trips to and from the islands, offering ever-changing views of docks, boats, and open water.
Mariner’s Church
Located at Fore and Moulton Streets, this church reflects Portland’s maritime roots and its role in abolitionist-era gatherings and publications.
Commercial Street
A lively waterfront thoroughfare where seafood spots, shops, and working piers come together, showcasing Portland’s enduring fishing culture.
United States Custom House
This imposing federal building once oversaw trade and imports, symbolizing Portland’s importance in national and international maritime commerce.
DiMillo’s Old Port Marina
A dockside restaurant and marina that pairs a nautical atmosphere with meals served right over the water.
Secondhand Clothing Store of Lloyd Scott
Marked on the Portland Freedom Trail, this site honors African American entrepreneurship and community life in Portland’s past.
Wharf Street
Formerly lined with warehouses, Wharf Street now offers close-up views of lobster boats, docks, and taverns tied to the city’s working waterfront.
Boothby Square
A modest public square surrounded by historic buildings, offering seating and a glimpse of Old Portland architecture without the crowds.
Friends Meeting House
For nearly 200 years, this Quaker meetinghouse has hosted worship, abolitionist organizing, and pivotal moments in Portland’s social history.
The Maine Lobsterman
A classic waterfront spot known for lobster rolls and harbor views, capturing the spirit of Portland’s seafaring traditions.
The Press Hotel
Set inside a former newspaper printing building, this boutique hotel blends historic craftsmanship with modern design.
Samuel Butts House and Store
Once both residence and shop, this building reflects a time when commerce and daily life shared the same roof.
Thompson Block
Noted for its decorative brickwork, this commercial building represents Portland’s ambitious rebuilding following the Great Fire.
Printers Exchange Block
A reminder of Portland’s early publishing and printing industries, which helped shape local media and public discourse.
Portland Observatory
Constructed in 1807, this octagonal tower once guided ships into Casco Bay and now offers sweeping views of the harbor from above.
Meeting Point
Your Portland walking tour begins at Casco Bay Lines, 56 Commercial Street, Portland.
Casco Bay Lines is found on Maine State Pier, near the junction of Fraklin Street and Commercial Street.
FAQs About Our Portland Audio Walking Tour
-
General admission to the Portland Observatory costs the following:
Adults: $10
Seniors / Military / Students: $8
Children (6–16): $5
Children (Under 6): Free
Portland Residents
Adults: $5
Children: $3
Visit the Greater Portland Landmarks website for more information.
-
Tours are fully refundable up to 24 hours in advance.
If it’s within 24 hours or you had an issue during your tour, email support@drivesanddetours.com. We review all requests individually and will always do our best to make things right.
Our goal is to ensure every traveler has a great experience exploring with Drives & Detours.
-
The Portland walking tour route is a loop, about 1.25 miles or 2 kilometers total. It takes about 1 hour and 20 minutes, giving you time to pause at each stop, explore, and enjoy the surroundings at a relaxed pace.
-
Yes, downloading the Drives & Detours app will give you full access to the tour you have purchased, as well as many other self-guided tours.
-
Download the tour before you go. Some areas have poor signal, which can make downloading the tour difficult. Once the tour is downloaded, it will work without any cell signal
The tour audio plays automatically as you approach each stop
Want to see more? Tap “View Stop” to see photos and bonus content
To return to the map, tap the small down arrow between the “previous” and “next” buttons
Follow the blue line and audio directions to stay on route
Use audio controls to pause, rewind, or skip—just like a podcast
Safety first: Keep your eyes on the road or sidewalk, follow traffic laws, and stay aware of your surroundings
-
No—download your Portland tour before you go, and you won't need a cell signal. Drives & Detours’ tours work without any cell signal once they are downloaded to your device.
-
Once you have purchased your Portland walking tour from Drives & Detours, you can use it whenever you want. You can always take the tour another day if the weather is bad on the day you plan to take it.
-
Unfortunately, Dives & Detours cannot guarantee that the Portland self-guided tour is accessible. People with wheelchairs, strollers, or mobility impairments are very welcome, but we recommend checking the Visit Portland website for detailed information.
Pro Tips for Your Drives & Detours Portland Self-Guided Tour
Download before you go.
Enable location services—GPS triggers the audio.
Use earbuds, headphones, or your car speakers.
Pause and resume anytime. If you take a break, just reopen the app and head back toward your last stop.
Lost your way? Tap any pin on the map, then tap the right-turn-arrow icon to open your default maps app for turn-by-turn directions to that spot.
Drives & Detours' New England Tours
Discover New England: Complete 7 Tour Collection!
Discover the highlights of New England with a curated set of seven self-guided tours covering some of the region’s most iconic destinations. Walk in the footsteps of revolutionaries along Boston’s Freedom Trail, unravel the events surrounding the Salem Witch Trials, and enjoy dramatic ocean views beside Newport’s grand mansions and Cliff Walk.
Nantucket Essentials Combo
See Nantucket from two complementary angles with this two-tour bundle. Start with a stroll through downtown Nantucket, where cobblestone streets, familiar landmarks, and GPS-triggered narration bring the island’s whaling-era story into focus.
Beyond the Cobblestones Self-Guided Walking Tour of Nantucket
Explore the historic core of Nantucket on a self-guided audio walk. Wander along Main Street, admire carefully preserved 18th-century homes, and stop at landmarks like the Atheneum, Hadwen House, and Straight Wharf as the island’s past unfolds around you.
Nantucket Coast to Coast Driving or Biking Tour
Travel across Nantucket from Madaket to Sconset on a flexible tour made for cycling or driving. Along the way, engaging stories introduce the island’s history, culture, and communities, transforming the journey into more than just a scenic ride.
Newport Cliff Walk Audio Tour
Stroll Newport’s legendary Cliff Walk while listening to stories that bring the mansion-lined shoreline to life. With panoramic Atlantic views as your backdrop, learn about the power, privilege, and people—both famous and forgotten—who shaped this storied stretch of coast.
Discover More
