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Old Port Historic Tours

Explore the Old Port's rich history from 1632 in this 2 1/2-hour exciting walking tour with over 50 historic stops! Your guide has a BA in History and is a Portland History Docent. You're in great hands!

Explore the Old Port and downtown Portland's rich history and places of interest from 1632 in this 2 1/2 hour, 2-mile, exciting walking tour and historical adventure with over 50 historic stops including historical landmarks, architecture, and monuments. We will also discuss famous and legendary people of the area, prohibition and how it all started in the Old Port, some of the hottest restaurants and craft beer bars, the best places for craft beer tastings, waterfront history, the Old Port's biggest fires, Underground Railroad, shopping, real estate history, night life, and much more! 

Popular Saturday tour tickets, as well as select Sundays, holidays, and cruise ship dates, are available from 11AM-1:30PM year-round (weather pending January though March).

Advanced tickets required at $45 per person. Kids 6 and under are free. Private tours and special group rates are available year-round! Private tour tickets are not available via Ticketmaster or Ticketweb so please call 646-845-9714 or email [email protected] to book. 

Leigh Rush Olson, your tour guide and founder of Old Port Historic Tours, holds a BA in History from CUNY Brooklyn College and is a certified Portland History Docent by the Maine Historical Society, in collaboration with Portland Landmarks. Moreover, Leigh is a Portland native (born and raised) and a resident of Kennebunk, Maine. You're in good hands! 

Here are just some of the topics you will hear about and places you will visit outside on an Old Port Historic Walking Tour with Leigh...

*Monument Square

*Lobsterman's Park

*Portland City Hall

*Old Port real estate history

*Numerous landmarks, monuments, and architecture on the National Registry of Historic Places

*US Custom House

*Boothby Square

*Commercial Street Waterfront

*Wharf Street

*Fishing industry

*Prohibition and how it all began in the Old Port

*Tommy's Park and the history of its murals

*Post Office Park

*Henry Wadsworth Longfellow Home

*Revolutionary Generation

*Civil War history

*First Parish Church

*Lincoln Park

*Several Underground Railroad stops

*Portland's tallest and oldest buildings

*Exchange Street galleries and boutiques

*Leigh's favorite places to point out for craft beer bars, breweries, and restaurants - including Leigh's favorite breakfast locations and where to get the best lobster rolls… BIG lobster rolls  🦞🦞🦞

*History of Portland's fires including the biggest that shocked the nation

*Famous/legendary people of the area

*Night life - stand-up comedy, concerts, theatrical performances, etc

*History of the Kotzschmar Organ- one of the grandest and most celebrated pipe organs in the world

*Local Maine Artists

*Old Port's finest Mansard roofs

*The Old Port's most popular donut shops, bakeries, and Mained themed treats 

*Best things to do in the Kennebunks if Portland isn't enough!

AND Much, Much, More, but Leigh doesn't want to give it all away!

Where to meet: Monument Square - located directly across the street from the Portland Public Library on Congress Street. 

  • Address Monument Square in downtown Portland, Maine
    Portland, Maine 04101
  • Phone 646-845-9714
  • Website
  • Payments Accepted accepts all major credit cards. Paypal for private tours.
  • Hours Popular Saturday tour tickets, as well as select Sundays, holidays, and cruise ship dates, are available from 11AM-1:30PM year-round (weather pending January through March), and are available at Private tours, with special group rates, are also available year-round and are booked though the tour guide directly at, emailing [email protected], or calling 646-845-9714. Let's go!

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