illustration by Donald Kyker, 1978
There are tales of a supposed first sighting of "something reptilian and unknown in the water" in the tidal estuary of Bush River by military in 1936, though the details of this are highly dubious.
1943 bring the next proposed first sighting, by Francis Klarrman and Edward J. Ward, outside of Baltimore. Per Weird Maryland (2006), written by Matt Lake:
This thing was about 75 yards [70 m] away, at right angles from our boat. At first, it looked like something floating on the water. It was black and the part of it that was out of the water seemed about 12 feet [3.5 m] long. It has ahead about as big as a football and shaped somewhat like a horse’s head. It turned its head around several times — almost all the way around.
The first firm sighting of what would become named Chessie was in July 1978, by Donald Kyker. Per Chessie: A Cultural History of the Chesapeake Bay Sea Monster (2024), written by Eric Cheezum:
The object as “the size of a telephone pole with its head raised above the water, moving down the river about 60 yards from shore. . . . Instead of undulating sideways, it undulated up and down.” “It was absolutely smooth, smooth as a snake or an eel,” Kyker was quoted as saying, “but it did not move through the water like a snake or an eel.” At first, Kyker believed he was witnessing a practical joke of some kind, or perhaps a group of otters swimming in a chain, but he quickly rejected these possibilities after neighbors downriver claimed also to have seen the creature. When newspapers reported the incident, experts on marine life in the region were quick to dismiss the sighting as a misidentification by inexpert eyes. But Kyker stood his ground—and the Chessie sensation was born.
Kyker’s neighbors, Howard and Myrtle Smoot, who owned a vacation home downstream in the same development, reported four strange creatures in the river, two of which they estimated at 30 feet long, and two at about 15 feet. Howard Smoot immediately went for his rifle and shot one of the creatures in the neck. It was not clear if the creature was injured: “It rose out of the water and disappeared,” Myrtle Smoot told reporter Anne Hazard of the Richmond Times-Dispatch. “Having children and grandchildren who swim and ski, we wanted to find out what it was. We didn’t know whether it was dangerous, and we figured if we could get one, we could find out what it was.” After firing on the creatures, members of the Smoot family took a rowboat out to where they had been in the river, to no avail. C. Phillip Stemmer, the Smoots’ next-door neighbor, was with them when they saw the creature. “Everyone who saw this was stone-cold sober as far as I know,” he told Hazard. “It was the oddest thing I’ve ever seen. I can’t relate it to anything.”
As reported sightings mounted and the media frenzy grew, doubt was given by officials. After all, for an incredibly busy (and shockingly shallow) bay, it was thought odd for a creature to suddenly appear out of nowhere. The name "Chessie" made it's first appearance in late 1978 (though it took until 1980 to find widespread usage), a pun off the much more famous "Nessie" in Loch Ness and the Chesapeake Bay.
Sightings largely disappeared by winter, and things fell quiet until June 1980. Again, per Chessie: A Cultural History of the Chesapeake Bay Sea Monster (2024):
The farmer in question was one Goodwin Muse, whose homestead was located on the Potomac River waterfront, adjacent to the birthplace of George Washington. Muse and the other witnesses gave a description similar to those reported in 1978: snakelike in form, but unusually long at 10 to 14 feet, about 5 inches in diameter, with a fist-sized head that projected out of the water as it swam. What Muse did not see, he took pains to explain, was the vertical undulation typical in accounts of two years before—a hitch in the ongoing construction of Chessie lore that would be quickly smudged over.
[...]
Muse, although not a waterman, was the next best thing. Not only was he credible, he was a native. “I’ve been here all my life around this river,” he was quoted as saying in the New York Times, “and this is something I’ve never seen before.”
More sightings followed soon after, with more fitting descriptions of the original side-to-side serpent locomotion. Local newspapers began offering monetary rewards for photos of the creature, though none ever came forward; some sightings were found with mundane explanations including one of the famous sightings revealed to be caused by a manatee. Again, Chessie sightings petered off as tourist season ended.
1982 brought the next big sighting, this time with a video recording of the event courtesy of the Frew family! Sadly, the tape was inevitably lost, with copies being of distorted, inferior quality, but not without an artistic reindition per the family's description. It was enough to truly put Chessie in the international spotlight.
Since then, sightings of Chessie were largely replaced by more substatial Chessie news. The creature became a symbol for environmental advocacy, with the U.S. Fish and Wildlife Service adopting it for educational materials. It's role as a local icon soon eclipsed reported sightings, though those sporadically still come about today.