Self-Guided Audio Tour of Portland’s Historic Old Port District Discount Tickets

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location pin icon Portland, USA
location pin icon Portland
5.0 /5
1 reviews
View all Self-Guided Audio Tour of Portland’s Historic Old Port District photos
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Self-Guided Audio Tour of Portland’s Historic Old Port District
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Overview

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

Meeting and Pickup

Meeting point

Casco Bay Lines is found on Maine State Pier, near the junction of Fraklin Street and Commercial Street.

End Point

End point

Boothby Square is not far from the starting point of the tour. It is found on Fore Street, between Pearl Street and Silver Street.

Language Offered

English-AUDIO

English-WRITTEN

Spanish-AUDIO

Spanish-WRITTEN

Itinerary

1. Moulton Street
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.
Duration: 5 mins
2. 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.
Duration: 5 mins
3. Tommy's Park
Across Exchange Street from Post Office Park, Tommy’s Park is a quaint plaza that offers benches under trees and views of mural-covered walls. It’s a calm pause amid the waterfront activity.
Duration: 5 mins
4. Casco Bay Lines
The ferry terminal where locals and visitors embark and return, giving views of islands, docks, and the sea’s shifting light. It’s both a transit hub and a scenic vantage.
Duration: 5 mins
5. Mariner's Church Banquet Center
Nestled at the corner of Fore and Moulton, the Mariner’s Church connects Portland’s maritime heritage with abolitionist history through its proximity to early printshops and meeting houses.
6. Commercial Street
Commercial Street is a bustling waterfront strip of seafood shacks, boutique shops, and views of working piers. This is where Portland’s fishing past and present meet.
Duration: 5 mins
7. United States Custom House
A stately building that once regulated trade and imports, the architecture of the United States Custom House recalls Portland’s deep ties to maritime commerce. It’s a solid landmark of federal presence amidst local hustle.
8. DiMillo's Old Port Marina
A floating restaurant and docked marina that blends nautical charm with delicious meals overlooking the bay. Here, you’ll find a unique way to dine with both water and history underfoot.
Duration: 5 mins
9. Wharf Street
Once lined with warehouses, Wharf Street now brings you close to the waterfront where you can see the working docks, lobster boats, and taverns that tell the city’s working-shore story.
Duration: 5 mins
10. Boothby Square
A small public square surrounded by historic buildings, offering benches, shade, and glimpses of old Portland architecture with little fanfare.
Duration: 5 mins
11. Friends Meeting House
This historic meetinghouse on Federal and Pearl Streets has been the site of abolitionist speeches, anti-slavery riots, and Quaker worship for nearly two centuries.
Duration: 5 mins
12. The Maine Lobsterman
An iconic waterfront restaurant and pub serving up fresh lobster rolls and seafood with views of working wharves. The Maine Lobsterman is a local flavor with a seafaring atmosphere.
13. The Press Hotel, Autograph Collection
Housed in a former newspaper printing facility, this boutique Press Hotel blends history, craftsmanship, and design. It’s also a good anchor point for exploring nearby Old Port streets.
14. Portland Observatory
Built in 1807, the octagonal tower of the Portland Observatory served as a maritime signal post, where watchmen helped ships entering Casco Bay avoid danger. The elevated deck now offers panoramic harbor views.

Inclusion

Flexible Usage (unlimited access)

Audio Guide

App and Tour Download

Exclusion

Smartphone (bring your own)

Cancellation Policy

Check mark icon Refundable tickets

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • 100% refund if cancelled 1+ days before the start date
  • 0% refund if cancelled less than 1 day(s) before the start date

Additional Info

Public transportation options are available nearby

Suitable for all physical fitness levels

Supplied by Drives & Detours

Reviews

5.0

★★★★★ ★★★★★
Based on 1 reviews

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