Private Tour
Available languages
Mobile ticket
Discover the vibrant history of Portland’s Old Port on this engaging walking tour.
Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom Trail, which honors the city’s fight for freedom and civil rights.
The tour showcases the Old Port’s architectural charm and its transformation from a bustling shipping hub to a cultural center. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalization efforts of the 1970s.
Join fellow history enthusiasts for a memorable journey through Portland’s past and present.
— Explore the historic Old Port district, a cultural and commercial hub
— Walk along the Portland Freedom Trail, learning about civil rights
— Discover stories of resilience, fire, and maritime life
— Ideal for history lovers and those curious about Portland's heritage
Public transportation options are available nearby
Suitable for all physical fitness levels
For a full refund, cancel at least 24 hours before the scheduled departure time.
A narrow, cobblestoned lane in Old Port lined with merchants and history, Moulton Street leads you past buildings once central to Portland’s trade. It’s also one of the stops on the Portland Freedom Trail.
Post Office Park
Located on the former site of Portland’s 19th-century marble post office building, this small urban green is now a shady, community gathering spot with a link to local history.
Flexible Usage (unlimited access)
Audio Guide
App and Tour Download
Smartphone (bring your own)
1 review
Total reviews and rating from Viator & Tripadvisor
Nomad661808,,Nov 29, 2025
- Review from Tripadvisor
The narration was very informative. The directions were clear and easy to follow. We learned a lot about the city. We were able to stop and take pictures whenever we wanted. If we got off the route, we were able to find our way back and finish the tour. And the tour is good for one year! So if we return, we can do it again!






Operated by Drives & Detours