Old Port Valentine's Holiday Historic Walking Tour


LOVE is in the refreshing and salty Old Port air! Explore the Old Port’s rich history and places of interest from 1632 in this casual 2 1/2 hour, 2-mile, exciting walking tour and historical adventure... 

Every year, since the 1970's, the "Valentine's Day Bandit" pins up 8x10 hearts all over the Old Port on the eve of Valentine's Day. Where will the bandit strike again? It's always exciting to see where the bandit strikes! This tour has over 50 historic stops and 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! 


Leigh Rush Olson, Your Tour Guide and founder of Old Port Historic Tours

Tour begins at 11AM and ends approximently at 1:30PM. Advanced tickets required at ticketweb.com. $45 per person. 

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 Old Port Valentine's Day Bandit 

*Valentine Bandit siting’s throughout the Old Port for photo opportunities. 

*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. 





Valentine's Day Bandit strikes again!