There were two children's books published about Chessie, the mascot for the Chesapeake and Ohio railroad. Neither is a Little Golden Book and both I'd consider difficult to find. The only copies I could locate went from $68-$400.
"Chessie and Her Kittens" by Ruth Carroll 1937
Chessie by Ruth Carroll 1936 (There's one on Ebay with an opening bid of $30
Good luck on your search.
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I'm looking for a book for my grandmother. She can't remember the title, but is pretty sure it was a LGB from the 1940's. She remembers that it was about a cat named Chessie who traveled on the Chesapeake and Ohio railroad. Any info would be helpful!