Original air date: 9/24/2004 (produced in 2003)
Once upon a time, Dora and Boots discovered the magical world of Fairytale Land. But when a mean witch tricks Boots into eating an enchanted banana, he turns into Sleeping Boots, who can only wake up with a hug from a true princess. Now Dora must face her hardest adventure yet — she must pass the four tests to become a true princess to wake up Sleeping Boots before the last leaf falls! Can the viewer help her become La Princesa Dora?
Tropes:
- Added Alliterative Appeal: To make Winter Valley even colder, the witch summons snowmen, snowballs, and storm clouds.
- Department of Redundancy Department: The Giant is addressed as the "Giant Giant".
- Deus ex Machina: Just after Dora summons Isa, Tico, and Benny to help her at the castle, the witch arrives and makes the stairs vanish so they won't be able to climb up. Just then, Dora remembers the magic hairbrush the animals gave her and she uses that to make her hair grow so her friends can climb up.
- Endless Winter: Winter Valley, until Dora turns it into Spring Valley with the bag of sunshine.
- End of an Age: This is the final episode in the series to use the "star catching" gimmick.
- Extra-Long Episode: The second in the series following "Dora's Pirate Adventure".
- Forced Sleep: Boots falls into one, becoming Sleeping Boots, thanks to the witch offering him an enchanted banana.
- Forced Transformation: The dragon at the Dragon's Cave was really a prince turned into a dragon by a spell long ago, until Dora finding the Red Ring broke the spell and turned him back to normal.
- Gorgeous Garment Generation: Dora's clothes change into a regal gown during her princess transformation.
- It Only Works Once: The enchanted items given to Dora (magic music box, bag of sunshine, magic hairbrush) will only work once, so she must only use them when she needs to.
- Magic Mirror: Dora encounters three of them whom the Seven Dwarfs use to alert her that Boots is still sleeping and the leaves are falling off the wall as they speak. The last time this happens, there is only one leaf left and there's only a matter of time left until it falls.
- Power Makes Your Hair Grow: The magic hairbrush causes Dora's hair to grow longer and longer until it reaches the ground. She uses such to help her friends up the tower when the witch takes away the stairs.
- Race Against the Clock: Dora has to become a true princess and wake up Sleeping Boots before the stone wall's last leaf falls.
- Rhymes on a Dime: Dora's four tests to become a true princess: Find the red ring, teach the Giant Rocks to sing, turn winter into spring, and bring the moon to the queen and king.
- Special Guest: Chita Rivera as the witch.
- Stalker Shot: After Dora leaves the Dragon's Cave after passing the first test, the Witch is seen watching her from afar, angered that she managed to find the Red Ring. She does this again after teaching the Giant Rocks to sing, that her henchmen are actually pleased for her before shutting them up in a haste.
- Transflormation: The witch disguises herself as a tree to trick Boots into eating an enchanted banana and falling into a deep sleep.
- Transformation Sequence: Dora gets a really good one when she transforms into La Princesa Dora.
- Vocal Evolution: Dora's voice has gotten a bit deeper due to Kathleen Herles experiencing puberty while entering her tween years.
- What Happened to the Mouse?: Backpack mysteriously disappears when Dora's clothes change into her princess gown, and doesn't appear again until "We Did It".
- Wicked Witch: The mean witch who lures Boots into a Forced Sleep.
- World-Healing Wave: When Dora puts on the red ring, it unleashes waves of magic which undoes the spell on the dragon, turning him back into a prince and the cave into his palace.
