Old Port Valentine's Day Tour! - Photo Credit: Leigh Olson

Old Port Valentine’s Day Tour!

LOVE is in the refreshing and salty Old Port air! Explore its rich history from 1632 in this 2 ½ hour, 2-mile, exciting and romantic walking tour! Every-year, since the 1970’s, the “Valentine’s Day Bandit” pins up 8×10 hearts all over the Old Port on the eve of Valentine’s Day. Where will the bandit strike again? It’s always fun to see where the Bandit strikes! With over 50 historic stops on this exciting tour… come see why people from all over fall in love with Portland’s breathtaking Old Port!

Events > Old Port Valentine’s Day 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
February 14, 2024

This casual walking tour (about 2 miles) has over 50 historic stops including historical landmarks, architecture, and monuments. We will also discuss famous/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, and much more! During the tour, expect a Valentine treat provided by Leigh Rush Olson, your Tour Guide and founder of Old Port Historic Tours. As aways, LGBTQIA+ friendly. Love is for all! 🏳️‍🌈💗

Your Tour Guide and founder of Old Port Historic Tours, 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 and a resident of Kennebunk with a passion for Maine’s history, so you’re in good hands.

Advanced tickets required at ticketweb.com. $45 per person. 18+ only please. Tour starts at 11AM and finishes approximately at 1:30PM. If you would like to speak with Leigh directly about the tour for questions, please email leigholson@oldporthistorictours.com or call 646-845-9714. Ticket sales turn off two hours before the tour.

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…

*Origins of the Valentine’s Day Bandit
*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!

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

Please visit oldporthistorictours.com for parking info, FAQs, etc.