Chessie

Template:Sister project Chessie may refer to:

• Chessie (sea monster), a legendary monster supposedly living in Chesapeake Bay, US
• Chessie System, a former holding company of the Chesapeake and Ohio Railway (C&O)
• Chessie (mascot), a kitten mascot of the C&O
• Chessie (train), a proposed streamlined passenger train of the C&O
• Chessie (band), an American experimental music group started in 1993
• Chesapeake Bay Retriever, a breed of dog