Events downtown

Feb 14

Old Port Valentine’s Day Holiday Historic Walking Tour
Location: Monument Square, Portland, Maine 04101, US
11:00 am - 1:30 pm
Event website

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 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 exciting to see where the bandit strikes! This tour has over 50 historic stops with 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! 🏳️‍🌈💗

Tour begins at 11AM and ends approximently at 1:30PM. Advanced tickets required at $45 per person. Age 18+ only please.

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, 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.