Chessie (sea monster) From Wikipedia, the free encyclopedia Jump to: navigation, search Chessie Creature Grouping Local Legend Sub grouping Sea serpent Data Country United States Region Chesapeake Bay Habitat Water Status Local Legend Chessie the Chesapeake Bay Monster at the 4th annual Maryland Faerie Festival, 2008.Chessie is a legendary sea monster said to live in the midst of the Chesapeake Bay. Over the years there have been many alleged sightings of a serpent-like creature with flippers as part of its body.