Self-Guided Audio Tour of Portland's Historic Old Port District
Drives & Detours
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
Departure Point
- Casco Bay Lines is found on Maine State Pier, near the junction of Fraklin Street and Commercial Street.
Return Details
- Boothby Square is not far from the starting point of the tour. It is found on Fore Street, between Pearl Street and Silver Street.
Duration
2 hours - 2 hours and 30 minutes
Languages Available
- Audio guide - English
- Printed guide - English
- Audio guide - Spanish
- Printed guide - Spanish
Points of Interest
Stop At: Moulton Street
Moulton Street, Portland, ME 04101
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 minutes
Stop At: Post Office Park
Middle Street, Portland, Maine
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 minutes
Stop At: Tommy's Park
175 Middle St, Portland, Maine
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 minutes
Stop At: Casco Bay Lines
56 Commercial Street, Portland, ME 04101
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 minutes
Stop At: Commercial Street
Portland, Maine
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.
Duration: Not Available
Stop At: United States Custom House
312 Fore St, Portland, Maine
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 minutes
Stop At: DiMillo's Old Port Marina
1 Long Wharf, , Portland, Maine
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.
Duration: Not Available
Stop At: Wharf Street
Wharf Street, Portland, ME 04101
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 minutes
Stop At: Boothby Square
330 Fore St, Portland, Maine
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 minutes
Stop At: Friends Meeting House
75 Pearl Street, Portland, ME 04101
A small public square surrounded by historic buildings, offering benches, shade, and glimpses of old Portland architecture with little fanfare.
Duration: 5 minutes
Stop At: The Maine Lobsterman
1 Temple Street, Portland, ME 04101
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 minutes
Stop At: Portland Observatory
138 Congress St, , Portland, Maine
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.
Duration: Not Available
Stop At: Mariner's Church Banquet Center
368 Fore Street, Portland, ME 04101
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.
Duration: Not Available
Stop At: The Press Hotel, Autograph Collection
119 Exchange Street, Portland, ME 04101
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.
Duration: Not Available
Additional Information
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Flexible Usage (unlimited access)
- Audio Guide
- App and Tour Download
Exclusions
- Smartphone (bring your own)
Redemption Instructions
IMPORTANT – YOUR ACCESS CODE IS: SPF628 - PLEASE READ STEPS BELOW - To access your tour, you’ll need the Drives & Detours App. We recommend downloading the tour in advance in case cell service is unreliable.
DOWNLOAD THE APP:
iPhone: https://apps.apple.com/us/app/drives-detours/id6443681888
Android: https://play.google.com/store/apps/details?id=com.mytoursapp.android.app6506
UNLOCK YOUR TOUR:
1. Open app, tap "Walking Tours", then "Portland’s Old Port"
2. Enter Your Access Code (on iPhone tap "Login to Download" then "Login")
3. Tap "Download Tour" and wait until complete (1-2 minutes)
STARTING THE TOUR:
1. Go to start location
2. Open app, select your tour
3. Tap “Start Tour”
ADDITIONAL NOTES:
Tour is valid for 180 days, no need to reschedule
Questions? TEXT us at 619.324.9920
Voucher Info
Mobile or paper ticket accepted
The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Drives & Detours in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.
This offer is not eligible for promo codes.
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
Departure Point
- Casco Bay Lines is found on Maine State Pier, near the junction of Fraklin Street and Commercial Street.
Return Details
- Boothby Square is not far from the starting point of the tour. It is found on Fore Street, between Pearl Street and Silver Street.
Duration
2 hours - 2 hours and 30 minutes
Languages Available
- Audio guide - English
- Printed guide - English
- Audio guide - Spanish
- Printed guide - Spanish
Points of Interest
Stop At: Moulton Street
Moulton Street, Portland, ME 04101
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 minutes
Stop At: Post Office Park
Middle Street, Portland, Maine
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 minutes
Stop At: Tommy's Park
175 Middle St, Portland, Maine
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 minutes
Stop At: Casco Bay Lines
56 Commercial Street, Portland, ME 04101
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 minutes
Stop At: Commercial Street
Portland, Maine
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.
Duration: Not Available
Stop At: United States Custom House
312 Fore St, Portland, Maine
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 minutes
Stop At: DiMillo's Old Port Marina
1 Long Wharf, , Portland, Maine
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.
Duration: Not Available
Stop At: Wharf Street
Wharf Street, Portland, ME 04101
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 minutes
Stop At: Boothby Square
330 Fore St, Portland, Maine
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 minutes
Stop At: Friends Meeting House
75 Pearl Street, Portland, ME 04101
A small public square surrounded by historic buildings, offering benches, shade, and glimpses of old Portland architecture with little fanfare.
Duration: 5 minutes
Stop At: The Maine Lobsterman
1 Temple Street, Portland, ME 04101
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 minutes
Stop At: Portland Observatory
138 Congress St, , Portland, Maine
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.
Duration: Not Available
Stop At: Mariner's Church Banquet Center
368 Fore Street, Portland, ME 04101
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.
Duration: Not Available
Stop At: The Press Hotel, Autograph Collection
119 Exchange Street, Portland, ME 04101
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.
Duration: Not Available
Additional Information
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Flexible Usage (unlimited access)
- Audio Guide
- App and Tour Download
Exclusions
- Smartphone (bring your own)
Redemption Instructions
IMPORTANT – YOUR ACCESS CODE IS: SPF628 - PLEASE READ STEPS BELOW - To access your tour, you’ll need the Drives & Detours App. We recommend downloading the tour in advance in case cell service is unreliable.
DOWNLOAD THE APP:
iPhone: https://apps.apple.com/us/app/drives-detours/id6443681888
Android: https://play.google.com/store/apps/details?id=com.mytoursapp.android.app6506
UNLOCK YOUR TOUR:
1. Open app, tap "Walking Tours", then "Portland’s Old Port"
2. Enter Your Access Code (on iPhone tap "Login to Download" then "Login")
3. Tap "Download Tour" and wait until complete (1-2 minutes)
STARTING THE TOUR:
1. Go to start location
2. Open app, select your tour
3. Tap “Start Tour”
ADDITIONAL NOTES:
Tour is valid for 180 days, no need to reschedule
Questions? TEXT us at 619.324.9920
Voucher Info
Mobile or paper ticket accepted
The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Drives & Detours in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.
This offer is not eligible for promo codes.
Need To Know Info
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts. Learn about Strike-Through Pricing and Savings