Trivia

According to writer and director David Swift, after looking at 362 girls for the part of Pollyanna, they still did not have anyone to play the part. One day, producer Walt Disney's wife Lilly went shopping with Disney studio head Bill Anderson's wife while they were in London, England, on business. The two ladies saw Hayley Mills in Tiger Bay (1959) and thought she was perfect for the role of Pollyanna. The two men didn't listen to them, but they were so persistent that the men finally agreed to watch the movie and immediately decided to cast Hayley.

When this movie performed below expectations at the box office, producer Walt Disney put out his theory for the movie's disappointing performance: "I think the picture would have done better with a different title. Girls and women went to it, but men tended to stay away because it sounded sweet and sticky."

Writer and director David Swift wanted to trim this movie by about twenty minutes and rearrange some scenes (most notably the acquisition of the doll in the town bazaar sequence). But producer Walt Disney, who had fallen in love with this movie by watching the dailies, would not allow it, and Swift did not have final-cut privileges.

This marks the first of six movies Hayley Mills made during her five-year contract with Walt Disney Studios.

Hayley Mills was awarded a special juvenile Oscar for her role in the film. This would be the last juvenile Oscar awarded. She was not present to accept the award, so Annette Funicello accepted it for her. Her father, i.e Sir John Mills, would not pull her out of school for the event. Hayley Mills told Entertainment Weekly in 2018 that she had no idea she'd won an Oscar until it arrived on her doorstep. She also had no idea the 1961 ceremony was being held or that she had been nominated.