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

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

By Drives & Detours

Free cancellation available

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Features

Free cancellation available
2h 30m
Mobile voucher
Instant confirmation
Multiple languages

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 honours 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 centre. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalisation 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

Activity location

Moulton Street
- Moulton Street
- 04101, Portland, Maine, United States

Meeting/Redemption Point

Casco Bay Lines
- 56 Commercial Street
- 04101, Portland, Maine, United States

Check availability

Self-Guided Audio Tour of Portland’s Historic Old Port District in Multilingual

2h 30m
Opening hours: Tue 8:00-20:00
English

Travellers

Languages available

Price details

S$12.71 x 1 AdultS$12.71

Total

What's included, what's not

Flexible Usage (unlimited access)
Audio Guide
App and Tour Download
Smartphone (bring your own)

Know before you book

Public transport options are available nearby
Suitable for all physical fitness levels

Activity itinerary

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.

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.

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.

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.

Mariner's Church Banquet Center (Pass by)

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.

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.

United States Custom House (Pass by)

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.

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.

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 storey.

Boothby Square

A small public square surrounded by historic buildings, offering benches, shade, and glimpses of old Portland architecture with little fanfare.

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.

The Maine Lobsterman (Pass by)

An iconic waterfront restaurant and pub serving up fresh lobster rolls and seafood with views of working wharves. The Maine Lobsterman is a local flavour with a seafaring atmosphere.

The Press Hotel, Autograph Collection (Pass by)

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.

Portland Observatory (Pass by)

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 harbour views.

Location

Activity location

Moulton Street
- Moulton Street
- 04101, Portland, Maine, United States

Meeting/Redemption Point

Casco Bay Lines
- 56 Commercial Street
- 04101, Portland, Maine, United States

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