Old Port December Holiday Historic Walking Tour


Holiday time in the Old Port is the place to be! Explore the Old Port’s rich history and places of interest from 1632 in this 2 ½ hour, 2-mile, exciting walking tour and historical adventure for all members of the family with over 50 historic stops including a stop outside the Henry Wadsworth Longfellow home (the oldest home on the Portland peninsula). While we are at the Longfellow home, you'll hear the history of his famous poem Christmas Bells. Moreover, during the tour, you will also hear the story of Charles Dickens bizarre visit to Portland. Don't miss it! 

Public tours will run every Saturday from December 3rd through Christmas Eve! Tour starts at 11AM and finishes approximately at 1:30PM. Advanced tickets required at ticketmaster/ticketweb. $45 per ticket. Kids 12 and under are no charge with a paying adult. Private tours and special group rates are available upon request any day of the week by emailing LeighOlson@OldPortHistoricTours.com, where you can pick your own time of day that is convenient for you! If you would like to speak with the Tour Guide, Leigh Rush Olson, directly about the tour for questions, please email or call 646-845-9714. 

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 popular donut shops - HiFi Donuts, Eighty 8 Donuts, and The Holy Donut 

*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.