This particular film has seven segments:
Once Upon a Wintertime features Frances Langford singing the title song about two romantic young lovers in December. The boy shows off for his girl, and near-tragedy and a timely rescue ensue. This short was also featured in Very Merry Christmas Songs which is part of Disney Sing Along Songs as a background movie for the song Jingle Bells.
Bumble Boogie is a surrealistic nightmare for a solitary bee trying to escape from a visual and musical frenzy. The music is courtesy of Freddy Martin and his orchestra (with Jack Fina playing the piano) and is a swing-jazz variation of Rimsky-Korsakov's Flight of the Bumblebee, which was one of the many pieces considered for inclusion in Fantasia.
The Legend of Johnny Appleseed is a retelling of the story of John Chapman, who spent most of his life roaming America and planting apple trees, thus earning his famous nickname. Dennis Day narrates and provides all the voices.
Little Toot is based on the poem by Hardie Gramatky, in which the title protagonist, a small tugboat, wants to be just like his father but can't seem to stay out of trouble. The Andrews Sisters provide the vocals. Out of all the musical segments, this one is the most famous.
Trees is a reciting of the famous Alfred Joyce Kilmer poem by Fred Waring and the Pennsylvanians with the lyrical setting seen through the seasons.
Blame It On the Samba has Donald Duck and José Carioca meeting with the Aracuan Bird who introduces them to the pleasures of the samba. The Dinning Sisters provide the vocals while organist Ethel Smith plays the organ.
Roy Rogers and the Sons of the Pioneers and Pecos Bill is the finale about the famous hero from Texas, the biggest and best cowboy that ever lived, his horse Widowmaker, and how he was brought back down to earth by a woman named Slue-Foot Sue. This retelling of the story is courtesy of Roy Rogers, Bob Nolan, and the Sons of the Pioneers to Bobby Driscoll and Luana Patten. This segment was later edited on the film's NTSC video release (but not the PAL release) to remove all scenes of Bill smoking a cigarette. The entire scene with Bill rolling the smoke and lighting it with a lightning bolt was cut and all other shots of the offending cigarette hanging from his lips were digitally removed.