Old Port Holiday Walking Tour - Photo Credit: Old Port Historic Tours

Old Port Holiday Walking Tour

Explore the Old Port’s rich history in this 2 ½ hour holiday walking tour with over 50 historic stops including Portland holiday history and stories that might surprise you! Your Tour Guide, Leigh Rush Olson, has a BA in history from C.U.N.Y Brooklyn College and is a Portland History Docent, as well as a Portland native, so you’re in good hands. Let’s explore holiday time in Portland’s beautiful Old Port! Private tours, with special group rates, available at oldporthistorictours.com. Let’s go!

Events > Old Port Holiday Walking Tour
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Monument Square
456 Congress St
Portland, Maine 04101 United States
About the Event
Presented by
Old Port Historic Tours
(646) 845-9714
December 2, 2023 through December 23, 2023

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 exciting walking tour and historical adventure with over 50 historic stops including historical landmarks, architecture, and monuments. We will also discuss waterfront history, the Old Port’s biggest fires, Underground Railroad, shopping, real estate history, night life, some of the hottest restaurants, craft beer bars, the best places for craft beer tastings, and learn about famous/legendary people of the area with a stop outside of 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 and hear the story of Charles Dickens bizarre visit to Portland. Don’t miss it!

Public tours will run every Saturday from December 2nd through December 23rd! 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 to promote historic preservation for our youth. Private tours and special group rates are available upon request, by visiting 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 leigholson@oldporthistorictours.com 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 most popular donut shops and bakeries
*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!

For meeting location, parking tips, direct link to buy tickets, and more FAQ, please visit oldporthistorictours.com.