Hayley Mills' first filmed scene was with Karl Malden: Reverend Ford is practicing his sermon in an open field. Distracted and losing her concentration, Mills hadn't got anything "in the can" by the time cast and crew broke for lunch. Her father, John Mills, took her aside to ask what was wrong. "Do you know what you are like?" he said. "You are like a great big white cabbage! Yes, really boring. Go on, pull your finger out." The afternoon's shooting went fine, but it was a long hot day "and Karl, I remember, got awfully sunburned. I always felt rather responsible."

Patty Duke auditioned for the plum part of Pollyanna.

David Swift: The fireman shown shooing the small boy off a ladder after the a boiler accident at the Harrington House Orphanage.

Roy Edward Disney, studio business head and brother to Walt Disney, issued thousands of "Pollyanna Photo Locket Necklaces" as a promotional item containing the famous quote attributed to Abraham Lincoln in the movie. Discovering the necklace in a gift shop while on vacation with his family, director / screenwriter David Swift called the studio to have the item recalled immediately. Lincoln never said, "When you look for the bad in mankind expecting to find it, you surely will." Swift had simply made it up.

According to 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, Walt Disney's wife Lilly went shopping with Disney studio head Bill Anderson's wife while they were in London on business. The two ladies saw Hayley Mills in Tiger Bay 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.

Apart from playing Jimmy Bean, Kevin Corcoran also did the narration for the Storybook Recording - a record that came packed inside the back cover of a softcover storybook you could read while listening to the record. Two of the songs that were dropped from the movie - "Pollyanna" and "The Glad Game" - were also included on the Storybook Recording.

Director / screenwriter David Swift had wanted to trim the overlong film by about 20 minutes and rearrange some scenes (most notably the acquisition of the doll in the town bazaar sequence) but Walt Disney, who fell in love with the film by watching the dailies, would not allow it and Swift did not have final-cut privileges.

Final film of Adolphe Menjou.

Marks the first of six films Hayley Mills made during her 5-year contract with Walt Disney studios.

The film opens with a close-up of a naked backside of young blond boy, who swings from a rope swing away from the camera jumping into a river. The boy is played by William Betz, who was 7 at the time of filming, who recalled in 2009 that at the time of filming, people weren't really allowed to swim in that river, White Sulfur Springs. He said his mother also had a very brief background extra role as one of the ladies at the train station where Pollyanna is picked up. Neither of them were actors but just locals where the movie was filmed. He is amused that the small Vermont town depicted in the movie was actually a mix of various locales miles apart in Napa Valley and Sonoma County, California.

The Orphanage house is still on the Warner Bros back-lot and sits next to the house used in Elvira: Mistress of the Dark.