The story begins with a scene at Walt Disney World's Magic Kingdom, where a young girl asks Disney Princesses like Snow White and Belle about the legendary Princess Winnifred. As the girl bumps into Carol Burnett, she begins to recount the enchanting tale.
Set in a whimsical kingdom, the narrative introduces a peculiar rule—no one can marry until Prince Dauntless played by Joseph Bova — finds a suitable bride. However, Queen Jane White, the reigning monarch, has exceedingly high standards and insists that only a genuine princess is fit for her son. Her criteria are so strict that every potential bride he seeks out quickly fails her rigorous tests. Despite her protests, Prince Dauntless becomes suspicious that his mother might be sabotaging his romantic endeavors, though Queen Aggravain (played by Jane White) denies any wrongdoing.
Meanwhile, a subplot unfolds involving Lady Larken played by Shani Wallis, who discovers she's pregnant with Sir Harry's child. The news sparks urgency because both of them need to find a bride for Dauntless to secure their own future marriage. Their efforts lead them to Winnifred, a spirited princess from the northern swamps, known for her wild nature and resilience. Winnifred arrives at the castle after swimming across the moat, immediately causing a stir. Although Queen Aggravain is repulsed by her, Dauntless is captivated by Winnifred's charm and genuine personality. His affection for her grows instantly, much to the queen’s dismay.
Queen Aggravain and her court then devise a test to determine if Winnifred is truly a genuine princess. The test involves placing a single pea beneath twenty mattresses, with the belief that only a true princess would feel the discomfort and avoid sleeping on such an uneven surface. As Winnifred prepares for the test, she is comforted by King Sextimus, the true ruler of the kingdom who is mute due to a curse (played by Jack Gilford), and his witty Jester [played by Elliott Gould], who explain that the curse can only be broken when "the mouse devours the hawk," hinting at deeper magic at play.
Winnifred's bright and lively personality is further showcased through her stories from swamp life and her carefree spirit during a croquet game, which even she suggests doing twice. Despite Queen Aggravain's plotting—secretly stacking twenty mattresses to set Winnifred up for failure and trying to exhaust her with a tiring dance called the Spanish Panic—the spirited princess survives the test and keeps her cheerful demeanor. Prince Dauntless expresses his love and admiration openly, declaring how different she is from the other princesses he’s encountered.
As plans unfold, Lady Larken secretly helps Winnifred by freeing her from her cell, hoping to foster her relationship with Harry. Meanwhile, Queen Aggravain and her allies hatch a scheme to make Winnifred fail by placing the pea under the bottom mattress and drugging her to sleep soundly while a lullaby sung by an actor dressed as a nightingale lulls her into rest. However, Winnifred, despite being drugged, feels something strange in her sleep and tries to find the cause.
The next morning, Queen Aggravain confidently announces that Winnifred must have failed, but Dauntless surprises everyone by declaring that she has passed the test after all. Winnifred had managed to stay awake and feel the pea, proving her sensitivity. Queen Aggravain tries to argue, but Dauntless stands firm, telling her to "shut up", which results in her being silenced—a symbolic moment that marks her loss of power. The curse on King Sextimus is also broken as he finally recovers his voice, and the court learns that the spell was actually about Queen Aggravain all along.
Rejoicing, Lady Larken and Harry decide to marry, and Dauntless and Winnifred are finally able to unite. Dauntless removes the pea from her mattress, confirming that Winnifred could feel it even if others tried to cheat. She sleeps peacefully, and the story concludes with a joyful celebration, signifying that they all lived happily ever after.
This charming fairy tale is a comedy filled with wit, magical curses, and the triumph of genuine kindness and love over strict rule and superficial standards.