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One Winter Weekendâs cast includes Taylor Cole, Rukiya Bernard, Dewshane Williams, and Jack Turner. One Winter Weekendâs Cast Taylor Cole as Cara. Taylor Cole is best known for her regular roles in television series The Event and Summerland.
Cast. 1  Nathan Gamble as Sawyer Nelson, an 11-year-old boy who finds Winter and cuts the crab trap off her. 2  Winter as herself, an injured dolphin that must have part of her fluke amputated. 3  Harry Connick, Jr. as Dr. Clay Haskett, the operator of the Clearwater Marine Aquarium in Clearwater and Hazel's father. Ashley Judd as Lorraine Nelson, Sawyer's mother and a nurse. Kris Kristofferson as Reed Haskett, Clay's father and Hazel's grandfather. Morgan Freeman as Dr. Cameron McCarthy, a prosthetic designer and Kyle's doctor at the VA Hospital. He agrees to help create a prosthetic tail for Winter.