Old Port December Holiday Historic Walking Tour


Holiday time in the Old Port is the place to be! Explore the Old Port and downtown Portland'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! We will begin our tour in the center of Monument Square, directly in front of the gorgeous City of Portland's Official Holiday Tree, to discuss the origins of the Christmas Tree and the first Christmas celebrated in America. During the tour we will discover over 50 historic stops, visit the magical Lobster Trap Tree in the heart of the Old Port, and hear the story of Charles Dickens bizarre visit to Portland. At the end of the tour, we will visit the outside of Henry Wadsworth Longfellow's famous home (the oldest home on the Portland peninsula) where you'll hear the history of his famous poem Christmas Bells. Don't miss it! 



Public tours will run every Saturday from December 7th through December 21st. Tour starts at 11AM and finishes approximately at 1:30PM. Advanced tickets required at ticketmaster/ticketweb. $45 per ticket. Kids 6 and under are free. Private tours and special group rates are available upon request by emailing LeighOlson@OldPortHistoricTours.com. If you would like to speak with the tour guide directly about the tour for questions, please email or call Leigh at 646-845-9714. 

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. Moreover, Leigh is a Portland native (born and raised) and a resident of Kennebunk, Maine. You're in good hands! Click here for more background about Leigh.

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 and the Offical City of Portland Holiday Tree

*Lobsterman's Park

*Portland City Hall

*Lobster Trap Holiday Tree in the heart of the Old Port at the Portland Regency Hotel

*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.