Helen Little worked for the Pennsylvania Railroad for many years as a switchboard operator in Louisville.
Little said, "The train went by my window and I always watched the caboose and I just thought that would be nice to ride in."
As the years passed, she never thought she would be able to ride in a caboose, until her family brought her to the Bluegrass Railroad Museum Monday morning.
Just days before she turned 89, her family had arranged for her to ride in the caboose of a train from Versailles to Lawrenceburg.
She said she loved the wonderful ride and was excited most of her family was able to join her.
Her granddaughter, who helped plan the trip, said, "You just don't know how many more you're going to have so we wanted to do something special."
Little said she is lucky to have such a great family that does so much for her.
She can't imagine what her family will plan for her next year when she turns 90.