Sea Monsters & Serpents, Long Island Sound

December, 2016 by Ray Bendici
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The Damned Story: With its maritime heritage, it's no surprise that Connecticut also has a rich history of sea monster and sea serpent sightings.

For centuries, Connecticut has been dependent on the sea. Native Americans spent a great deal of time on the water, fishing and harvesting oysters, and once the first Europeans arrived, thousands of livelihoods have been made by fishing, lobstering, clamming, whaling and catching other delicious water critters. Our coast has been critical to the settlement and development of the nation, not only because of the abundance of trading ports but also due to its vital role in the shipbuilding industry—literally thousands of ocean-going vessels have been launched from the shores of Connecticut.

In short, we've been on the sea a lot.

As such, eyes have been on the waves for hundreds of years and there have numerous sightings of unusual creatures in the waters around Connecticut—accounts of sea monsters being seen in New England date back to 1638. When newspapers started being printed, such events began to be chronicled on a more regular basis.

Like in much of the world where the sea plays an important role, there have been accounts of giant water snakes and squids as well as more unusual creatures, such as mermaids.

This site detailing the history of Lordship in Stratford has an excellent page dedicated to historical sea serpent sightings (as well as a mermaid sighting!). Although the entire page is well worth reading, here are a few gems:

  • From Sept. 17, 1878—A sighting off the shore of Stratford by Mr. Kelley, a "sober, trustworthy man": Not far from the side of the vessel he saw the head of a monster raised several feet above the waves. The hour, about sunset, was light enough to show the creature plainly; it was seemingly not fifteen rods off. It was a horrible looking head, with a wide open month. The head disappeared and a portion of the body was shown, forming an arc under which it would have been easy, so far as space is concerned, to have driven a team of oxen. There were several smaller curves, indicating a long body. The object disappeared in a few seconds, before Mr. Kelly who was standing alone in the midship gangway could call anyone to see it. He describes the body as being as large round as that of a big horse.'
  • July 18, 1895—The first-person narrative of Capt. Obadiah Donaldson, whose crew allegedly fought off a 60-foot-wide octopus with 100-foot-long arms after accidentally crashing into it! He was in a deep sleep, and his snores could be heard quite a way off. But I was too late. The boat struck him amidships. He awoke in a jiffy. At first he thought we wore a nightmare, but he rubbed his eyes and identified us as enemies, though heaven know: I had no wish to fight him. He darted at us, kicking up the sea. One of his long arms came aboard and seized the forward steam windlass. He wound his arm around it, thinking, I suppose, that it was a sailor. The mate, with great presence of mind started the windlass, and in less time than it takes to tell it a couple of hundred feet of the arm was wound in, and we had the fish a prisoner. But we'd caught a Tartar. He began to pull at the boat, and I was afraid he meant to sink it and eat us at his leisure. The vessel rocked, and I thought she would capsize every minute. I called to Frank Taylor, the boatswain, to cut off the arm and he did so with a meat chopper. Eventually, the octopus was run off by a group of porpoises!
  • July 18, 1909—The tale of a Stratford lighthouse keeper, who confronted an odd creature from the water that was stealing his chickens. Pulling up the gun, Mr. Judson let fly with both barrels. There was a grunt of pain and a sound as of some heavy body struggling on the sand. Then all was still. Getting a lantern, Mr. Judson found on the beach a huge fish the like of which be never saw before. It resembled a flatfish or a skate as much as anything only is was nearly a yard long and was afterward found to weigh sixty pounds. The beast was almost black in color and differed from a flatfish in that it had a mouth that extended the entire width of its head and was armed with long, sharp teeth like those of a shark. The mouth when distended was large enough to accommodate a derby hat. Along the creatures back extended a row of sharp spines while over each eye, which was as large as that of a human being, was a feeler fully a foot in length. The strangest part of the whole fish was the presence on its underside of two flippers identically like those of a turtle.

Serpents have not only been spotted in the Sound. An 1886 story from The New York Times details how a 100-foot monster was encountered all the way up the Connecticut River in Cromwell. From the story:

Out of the froth rose a big black head as large as a flour barrel and with eyes as big as small plates. The head kept rising higher and higher until 10 feet of the neck appeared. The men didn't stop to make a long or thorough examination, but they feel sure that the sea serpent must have been a clear hundred feet long.

The article goes on to say that despite many people coming out to see it, the creature was not seen again.


Sometimes it wasn't always a pitched battle between man and beast, as witnessed in this July 3, 1881 article from the Times when a yacht with "a party of New-London gentleman" came across "a veritable sea serpent" between Montauk and Block Island, who "as the yacht passed, he raised his head and took survey of the surroundings. He was the color of gulf weed, mottled with black spots, and was about 40 feet long." Apparently, the creature was out for a pleasure cruise, like the gentlemen aboard the ship.

Obviously, many of these sea serpent reports fall under the category of fictional "fish stories" while others are most likely exaggerated descriptions of encounters with genuine out-of-place denizens of the ocean, such as oarfish or manatees. Of course, there's always a chance a few stories are genuine—the ocean is a big place, of which we haven't even explored a fraction yet. Without any physical evidence, these reports will just remain stories.

Although sea serpent sightings have declined drastically over the last century, unusual things are still seen from time to time. In October 2008, an unidentified creature washed up on a New London beach, which drew a lot of "monster" speculation before it was essentially identified a badly decomposed raccoon.

Sadly, we have no particular monster associated with the state, say like a Nessie or Champ, although we've heard tales about Trappie, the mysterious creature that haunts the Trap Falls Reservoir in Shelton. (And by "have heard tales," we mean "have tried to fabricate our own urban legend to no success.")

Still, we will continue to hear stories of sea monsters and other freakish water creatures until Connecticut no longer has access to the coast, which won't be for a long, long time.

Our Damned Experience: Despite spending countless hours laying about at Connecticut beaches as well as the occasional trip out on the Sound, we have yet to see any fierce sea beasties.

If You Go: The Connecticut coast and Long Island Sound are pretty much open to everybody—just head south from anywhere in the state and eventually you'll hit the water.

If you ever see any sea serpents or monsters frolicking about the Sound, please let us know. Likewise, we will post any pictures of unusual creatures spotted near our shores.

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Reading about these wonderful old sea tales is near and dear to me. I've written a children's book about a mermaid, and find these old news accountings serve to just completely unbridle the imagination. The oceans are so vast, still so unexplored, and so mysterious, but what's even more mysterious is the individual mind that perceives these events, such as the Stratford Lighthouse Keeper.

Submitted by Steve( (not verified) on
Was it a sea robin?

Submitted by Chris (not verified) on
This memorial weekend I was at the Norwalk beach, and My friend and I seen a crazy creature. It was nothing like we ever seen before it was orange and black long and cant tell what it was. I don't know what it resembled but to me it might of had legs like a centipede but to my friend it looked more like a snake. If you have a idea please let figure this out.

Thank you for the kind words about my website. I found the articles from various sources including which is a site that you have to subscribe to.

These are just some of the reasons why I do not like being in an open water.

Submitted by Bob Saget (not verified) on
cool story

Submitted by Jon Stone (not verified) on
I kayaked to a little island here in Greenwich where there was a No Hunting sign. I wondered what it could be talking about, but then i saw in the sand, footprints. They looked 2-legged -- alternating, not in pairs -- and like cloven hooves. Someone told me deer can swim but that doesn't sound right. I've seen a lot of foxes too, but these were fresh prints and looked like these: