The film is the 11th Walt Disney theatrical animated feature and is the last of the studio's package film era of the 1940s, following Saludos Amigos, The Three Caballeros, Make Mine Music, Fun and Fancy Free, and Melody Time. Beginning in 1955, the two portions of the film were separated, and televised as part of the Disneyland television series. They were later marketed and sold separately on home video.
The Wind in the Willows: This segment is based on The Wind in the Willows (1908) by Kenneth Grahame, and is set in and around London c. 1908. The protagonist J. Thaddeus Toad, Esq. is introduced as an "incurable adventurer" who "never counted the cost". Although he is the wealthy proprietor of the Toad Hall estate, Toad's adventures and "positive mania for fads" have brought him to the brink of bankruptcy. As a last resort, Toad's friend Angus MacBadger volunteers as Toad's bookkeeper to help Toad keep his estate which is a source of pride in the community.
One day, MacBadger asks Toad's friends Ratty (a water rat) and Moley (a mole) to persuade Toad to give up his latest mania of recklessly driving about the countryside in a horse and cart, which could accumulate a great deal of financial liability in damaged property. Ratty and Moley confront Toad, but cannot change his mind. Toad then sees a motor car for the first time and becomes entranced by the new machine, taken over by "motor-mania."
To cure Toad's new mania, Ratty and Moley put Toad under house arrest. But Toad escapes and is later arrested and charged with car theft. At his trial, Toad represents himself and calls his horse Cyril Proudbottom as his first witness. Cyril testifies that the car which Toad was accused of stealing had already been stolen by a gang of weasels. Toad had entered a tavern where the car was parked and offered to buy the car from the weasels. However, since Toad had no money, he instead offered to trade Toad Hall for the car. Toad then calls the bartender Mr. Winky as a witness to the agreement; however, when told by Toad to tell the court what actually happened, Winky falsely testifies that Toad had tried to sell him the stolen car. Toad is found guilty on the spot and sentenced to twenty years in the Tower of London. Toad's friends make every effort to appeal his case, but with no success.
That Christmas Eve, Cyril visits Toad in disguise as his grandmother and helps him escape by giving him a disguise of his own. Meanwhile, MacBadger discovers that Winky is the leader of the weasel gang, and that they have indeed taken over Toad Hall; Winky himself is in possession of the deed. Knowing that the deed bearing Toad and Winky's signature would prove Toad's innocence, the four friends sneak into Toad Hall and take the document after a grueling chase around the estate.
The film then ends with Toad regaining his house while it implied Winkie and his minions have been arrested and imprisoned. As McBadger, Ratty and Mole celebrate the New Year with a toast to Toad, who they believe has completely reformed, Toad and Cyril recklessly fly past on a Wright Flyer; Toad has not truly reformed and developed a mania for airplanes.
Ichabod Crane: The second segment is based on "The Legend of Sleepy Hollow" by Washington Irving. Although the film introduces the story as Ichabod Crane, later individual releases retained the story's original title.
In October 1790, Ichabod Crane, a lanky, gluttonous, superstitious yet charming man arrives in Sleepy Hollow, New York, a small village north of Tarrytown that is renowned for its ghostly hauntings, to be the town's new schoolmaster. Despite his odd behavior and awkward appearance, Ichabod soon wins the hearts of the village's women. Brom Bones, the roughish town hero, does his best to bully Ichabod. However, he is very good at ignoring these taunts and continues to interact with the townspeople. Ichabod then falls in love with eighteen-year-old Katrina van Tassel, the beautiful daughter and only child of Baltus van Tassel, who is the richest man in the village.
Despite the fact that he is falling in love with her, Ichabod secretly intends to take her family's money for himself. Brom, who is also in love with her, proceeds to compete with the schoolmaster. Ichabod wins Katrina over at every opportunity, although, unbeknownst to him, Katrina, who thinks Brom is too sure of himself, is only using Ichabod to make Brom jealous and very disappointed in him.
The two love rivals are invited to the van Tassel Halloween party where Brom tries to swap a plump woman for Katrina who is dancing with Ichabod but comically fails. While both men dine Brom catches Ichabod tossing salt over his shoulder. Discovering Ichabod is superstitious, he decides to sing the tale of the legendary Headless Horseman who was apparently killed by a cannonball in a recent conflict and travels each year on Halloween while searching for a head to replace the one he had lost. Everyone else including Katrina find this amusing while Ichabod on the other hand gets paranoid.
On his way home from the party, Ichabod becomes paranoid by every animal noise he hears while riding through the dark woods, increasing his fear of the possibility of encountering the Horseman. While traveling through the old cemetery, Ichabod believes he hears the sound of a horse galloping towards him, but discovers the sound is being made by nearby cattails bumping on a log. Relieved, Ichabod begins to laugh with his horse. However, their laughter is cut short by the appearance of the real Headless Horseman riding a black horse. After the ghost gives chase, Ichabod, remembering Brom's advice, crosses a covered bridge, which stops the ghost's pursuit. However, the horseman throws his flaming head, revealed to be a great big jack-o'-lantern, at a screaming Ichabod.
The next morning, Ichabod's hat is found at the bridge next to a shattered pumpkin, but Ichabod is nowhere to be seen. Sometime later, Brom takes Katrina as his bride. Rumors begin to spread that Ichabod is still alive, married a wealthy widow in a distant county with children who all look like him. However, the people of Sleepy Hollow insist that he was "spirited away" by the Headless Horseman.
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