24 Hours in Portland, Maine Legends and Seamonsters

Shipwrecked Sailors and Seamonsters

An Overview of Portland Legends:

There are heaps of legends that rise from the cold and jagged coast of New England, and what better place to explore them from than Portland, Maine. With its first settler arriving in 1623 by the name of Christopher Levett, Portland has seen it’s share of shipwrecked sailors, pirates, and disaster… and maybe even a sea monster or two.

One of the many Islands in Casco Bay by Christa Thompson

One of the many Islands in Casco Bay by Christa Thompson

 Check out this sweet old news article I found when doing my research on pirate legends in Portland, Miane

Portland is a beautiful city that overlooks some of North America’s most volatile waters. The water is cold and fierce, with weather conditions that are unpredictable and often dangerous. Waves that dance with ships just as they can swallow them whole. It is no wonder the waters of the New England Coast are so alluring and mysterious, often leaving nothing but sunken treasures and widowed wives behind.  If you’re in town for a short bit, here are a few cool things to do in 24 hours in Portland, Maine.

The streets of Portland, Maine.

The streets of Portland, Maine.

Explore the City

There’s shopping and dining in town. You can enjoy a nice walk along the pier and take in the Maine culture in the crisp fall air.We found a really cool comic book store that shared an underground space with an awesome B movie rental joint and a pizza shop. For the win!

Portland History

Officially settled in 1633 and named Casco, Portland was a fishing village that saw more than just a death toll in its waters. Over a 100 year span it was destroyed three times, and again in 1866 during the ‘Great Fire’, leaving more than 10,000 people homeless. It is notably the home of Henry Wadsworth Longfellow and the site of one of the most northernmost battles of the Civil War, the Battle of Portland Harbor.

I was surprised to see a piece of the Berlin Wall in Portland, Maine. A bonus for me for the day! Very cool.  by Christa Thompson

I was surprised to see a piece of the Berlin Wall in Portland, Maine. A bonus for me for the day! Very cool. by Christa Thompson

Such a friendly staff, they made a great impression by Christa Thompson

Such a friendly staff, they made a great impression by Christa Thompson

Take a Lighthouse Tour Cruise

After a 6 hour road trip from Sleepy Hollow where I was scared out of my socks at the Horseman’s Hollow event, I was ready to relax and explore the lighthouses off the coast of Portland in the very waters where, like many pirates and sailors, Christopher Levett, once sailed.

Off the coast of Portland there are lovely towns on craggy cliffs.

Off the coast of Portland there are lovely towns on craggy cliffs.

Aboard the ‘Islander’, a Portland Discovery Land & Sea Tours vessel, on the dominating waters off the Casco Bay, the air was cold but the view was captivating. We spent two hours cruising the bay as our knowledgeable guide gave detailed accounts of the lighthouses, islands and forts that we encountered. The tour was relaxing, educational, and provided one of a kind views of the lighthouses. However, I didn’t see any sea monsters, they would be better found at the International Cryptozoology Museum just up the road in town.

A view from Chandlers Wharf by Christa Thompson

A view from Chandlers Wharf by Christa Thompson

Click here to read more about my Portland lighthouse tour

The Feegee Mermaid  by Christa Thompson

The Feegee Mermaid by Christa Thompson

Visit the International Cryptozoology Museum

Back on land, I made my way over to the museum where I met with Jeff Meuse, Assistant Director of the International Cryptozoology Museum of Portland, home to the bizarre, rare and diligent collection of the world’s most legendary and mythical creatures (‘cryptozoology’ is more scientifically stated as “the study of hidden animals”). Wouldn’t you know, I found a sea monster, among other things.

Click here to see what legendary creatures are creeping around at the International Cryptozoology Museum

What else are you going to eat lol... This was a good spot to enjoy the sunset and fresh caught lobster at the Portland Lobster Company at the dock where the Portland Discovery Land & Sea Tours are, by Christa Thompson

What else are you going to eat lol… This was a good spot to enjoy the sunset and fresh caught lobster at the Portland Lobster Company at the dock where the Portland Discovery Land & Sea Tours are, by Christa Thompson

Grab a Maine Lobster On Casco bay

Nothing fancy just paper plates, corn on the cob and the best darn lobster you’ve never had.

Fort Allen Park a really cool park to unwind at, awesome for hill rolling, on the water with a playground, by Christa Thompson

Fort Allen Park a really cool park to unwind at, awesome for hill rolling, on the water with a playground, by Christa Thompson

Watch the Sunset at Fort Allen Park

It was an eventful day. I never thought I would have seen a headless horseman, toured the notoriously haunted Lizzie Borden House, driven 6 hours, chartered the coast of Portland, and taken a picture with Bigfoot all in one 24 hour period. I just needed a bottle of water, a bed and a hot shower. I was more than eager to check into my digs for the night at the Portland Harbor Hotel. So far so good, place looked pretty fit, but I’ve seen this before… wasn’t going to hold my breath until I made my way into the room.

Click here to read about what surprise I found behind my hotel door…

Other points of interest in Portland, Maine:

Wadsworth-Longfellow House

Victoria Mansion

Longfellow Arboretum

This is a place for the whole family. Portland, Maine with its history and legends has laid its culture between every brick in its city. It adds a special piece to the diverse puzzle of America. A picturesque big-little town that no matter how cold it gets, is always warm.


About Christa Thompson

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Christa Thompson is the Founder and Senior Editor of The Fairytale Traveler. Christa has been traveling the world since 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day. "It's never too late to believe in what you love and to pursue your dreams." -Christa Thompson

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