24 Hours in Portland, Maine Legends and Seamonsters

24 Hours in Portland, Maine Legends and Seamonsters

Wandering through the narrow cobblestone streets of #Portalnd, I discovered it is defiantly worthwhile to explore the small vibrant city, filled with redbrick warehouse’s and Victorian mansions. If you can handle the #history of the urban legends, then make your way to the museum of cryptozoolodgy, and if too spooky, then #relax at the lively waterfront where there a plenty of options to get a bite to eat.


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
One of the many Islands in Casco Bay

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.

Portland is a beautiful city that overlooks some of North America’s most volatile waters. 

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.

it was destroyed three times, and again in 1866 during the ‘Great Fire’, leaving more than 10,000 people homeless.

Berlin Wall in Portland, Maine
Berlin Wall in Portland, Maine

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.

on the dominating waters off the Casco Bay, the air was cold but the view was captivating.

from  $26

Lighthouse Lovers Cruise Tour in Portland

ActiveCulture
 Portland, OR, United States
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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
A view from Chandlers Wharf
The Feegee Mermaid
The Feegee Mermaid

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.

home to the bizarre, rare and diligent collection of the world’s most legendary and mythical creatures

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
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

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

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.

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.

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