CHAPTER 1: The Barton twins, Judy and Jimmy discover the silver Star, which goes on the top of their Christmas tree, is missing. It is recalled that Uncle Ned took some of the holiday decorations up to, the attic last year and, after some pleading with Mother, the twins are permitted to go up to search for it. They don't find the star but they do discover a number of other interesting things, including a tiny, 4-inch-tall teddy bear with a green ribbon around his neck. Jimmy looks through an old seaman’s telescope and sees the little bear move. He introduces himself with his own song “I'm the Cinnamon Bear with the Shoe Button eyes.” Paddy O'Cinnamon, for that is his proper name, tells the children their star has been stolen by the Crazy Quilt Dragon and offers to help them get it back.
CHAPTER 2: Paddy shows Judy and Jimmy how to de-grow, that is, shrink to his own 4-inch size, so they can fit into his very own special airplane end they set out for Maybeland. Shortly after take off, they are overtaken by the old Stork. Terribly thirsty, the bird taps into the plane's 'soda pop fuel tank. Out of 'gas,' our adventurers are forced to land at the bottom of Looking Glass Valley, whose sides are so steep that no escape is possible.
CHAPTER 3: The Stork reappears, apologizing for causing them problems and offering to fly them to the top of the cliffs which overlook the Root Beer Ocean. There they discover Crazy Quilt, with the Star, sound asleep. Awakening him with a Boo, the frightened dragon falls over the cliff into the ocean below. After he swims ashore, the patchwork explains in song why one must “Never Say Boo to a Crazy Quilt Dragon." He apologizes succumbing to the temptation to steal the shiny star. Unfortunately though, he cannot return it because he lost it when he fell into the Root Beer Ocean.
CHAPTER 4: Jimmy, Judy, Paddy and Crazy are approached by a most peculiar group of people. They are the Inkaboos, the blotter people who are a bit touchy about their boundary lines. After a brief struggle, Crazy Quilt escapes but our three friends are made prisoners. They are taken before King Blotto and charged with trespassing, the penalty for which is to be thrown into the Immense Inkwell.
CHAPTER 5: The execution is delayed when it's discovered that the Royal Executioner is off for the day and his assistant can’t recall the exact wording of the ceremony. While the Inkaboos debate what to do, Crazy Quilt returns with the Scissors Soldiers who engage them in battle. In the turmoil, our group escape on the back of the dragon, who swims out to sea and safety. Judy spots the Silver Star floating on the surface of the water, but before they can recover it, the ornament is swallowed by Wesley the Wailing Whale.
CHAPTER 6: The Wailing Whale explains in song why it enjoys ill health. Crazy Quilt hits on the idea of tickling the polka-dotted Wesley until he coughs up the star. It works, but the star is, in turn, caught by Samuel the Performing Seal, who insists on Juggling it on his nose. One final toss of the star into the air, however, attracts Penelope the Pelican, who catches the shiny bit in her beak and flies off.
CHAPTER 7: Crazy Quilt swims our friends to show to dry out. They meet an incompetent magician, Mr. Presto, who, in demonstrating his magical prowess, mistakenly pulls Penelope from his hat. The angry bird complains that when the magician so rudely summoned her she dropped the star while flying over the Island of Obi. The group looks along the shore for a boat to take them to Obi. They discover, instead, a treasure chest and, moments later, they are surrounded by a band of Pirates.
CHAPTER 8: Crazy Quilt flees again and the rest of our friends are hustled into the buccaneers longboat and, as prisoners, are taken aboard the anchored pirate ship, the Suzy Q. There they learn from Capt. Tatty that their supposed captors are the Candy Pirates and friendly follows indeed. The pirates agree to sail to Obi. As they approach the island's shores, they see through a telescope a big Roly Poly Policeman patrolling the beach. And on the lapel of his uniform is pinned their Silver Star.
CHAPTER 9: The pirates give them a small boat to row to shore and then sail off. But a Magic Wave prevents them from getting through the surf. They try again a few hundred feet down the shore and find the water calmer. Landing on the beach they return to find the Roly Poly Policeman, but the star is gone from his chest. The Irish-brogued cop explained that a fellow who said he was a friend of theirs came to collect the star, then ran on up the beach in the opposite direction. From the policeman's description, it could have been none other than Crazy Quilt. Our group follows but as they are running along the sand, Paddy O'Cinnamon disappears.
CHAPTER 10: Paddy, it seems, crossed an invisible boundary line, and so do the children, reuniting the group once again. An educated owl. Professor Whiz tells them that he'd spotted Crazy Quilt run into the nearby home of the feared Wintergreen Witch. They follow but find the home empty, except for a magical picture of a great forest. Stepping through the frame of the Picture into the woods, they meet tiny Fraidy Cat, who in a wee voice tells of a great giant who lives there. The trio and the kitten try to run when the giant approaches.
CHAPTER 11: The Giant. Fee-fo is huge, but gentle and a real friend. He takes Jimmy, Judy and Paddy to the Goody Good Grove where they have an elegant Banquet. As night falls suddenly on the Magic Forest, they spot two scary yellow lights in the darkness.
CHAPTER 12: The lights are really Crazy Quilt's eyes. The witch has put him in a trance. When they wake him, the three friends learn to their dismay that Wintergreen has stolen the star from Crazy Quilt. Anxious to return to the witch's home, but lost in the woods, Jimmy recalls the whistle given him by Fee-fo. Three blasts on the whistle will bring the gentle giant to help. But when Crazy Quilt tries, he inhales too deeply and swallows the whistle.
CHAPTER 13: The dragon, however, still manages to toot for help and Fee-fo arrives to rescue them. He is too large to return with them through the picture frame. The four adventurers, though, confront the witch in her home. Not only does the hag refuse to return the star, she threatens to use magic to transform them into all manner of horrible things. She is horrified, however, at her own reflection in Judy's pocket mirror, and gives them back the star. The children foolishly let Crazy Quilt put the star in his hip Pocket. And when they return to Maybeland from Obi, the dragon sits down and crushes the ornament to bits.
CHAPTER 14: The dragon suggests they go to the castle of Queen Melissa to get help in repairing the star. The Grand Wunky, the royal attendant, ushers them into the presence of the beautiful and kindly queen.
CHAPTER 15: Queen Melissa writes special instructions and seals them in an envelope, telling Judy and Jimmy that they will help them to restore their precious Silver Star. But the instructions can be read only in complete darkness. The Grand Wunky suggests they may find total darkness in the Wishing Woods, and directs them. Just inside the woods, they encounter bathtub singer, Snappersnick, the Crooning Crocodile. The friends are horrified though, when Snappersnick swallows the instructions.
CHAPTER 16: It turns out that the croc is near-sighted, but can 'absorb' the contents of any writing by eating it. He tells them that Melissa's note tells them to go to the Wishing Well. En route, they meet Oliver the Ostrich, a Cockney fellow who loves eating alarm clocks and bacon. Eventually they reach the Wishing Well, but alas, Paddy leans over too far and falls in.
CHAPTER 17: The only way to rescue poor. CINNAMON BEAR is to use up the only wish allowed them. Wearily Judy Jimmy, Paddy and Crazy Quilt trudge back to see Melissa for fresh instructions. But they come to a river of mud and the awful Muddlers, who toss our hero's into the quagmire.
CHAPTER 18: As they are about to sink beneath the mud, they are rescued by the Cockle Burr Cowboys. The wanglers, fortunately, work for Melissa and, through them the children speak to the queen again. She is sympathetic and gives them new directions. Leaving the cowboys behind they set out across the Purple Plain toward the Golden Grove, where they are to find the Singing Tree and a further clue. But, horrors, they hear bloodcurdling War whoops. It's Indians!
CHAPTER 19: It's only Chief Cook'n Bottlewasher, who has been attracted to Crazy Quilt's colourful pelt, which he wants. But Judy persuades him to take her pocket mirror instead. Just when they reach the Golden Grove, the evil Wintergreen reappears. She demands the broken star and, since Judy no longer has the protective looking glass, Jimmy is forced to surrender the pieces of the star to Wintergreen.
CHAPTER 20: A still angry witch is about to turn our friends into bullfrogs but discovers Queen Melissa has taken away her magical powers. The Grand Wunky reappears and forced the helpless witch to return the star and takes the old hag away in custody on the queen's orders. Tired, the adventurers fall asleep under a tree. When they awake, they discover a huge silk Flying Hat.
CHAPTER 21: In the Fly Hat they take off for the Snow Country. There, on Melissa's instructions, they hunt for someone known as Nicky Froodle. A W.C. Fields-sounding snowman directs them to a nearby castle and the little elf named Nicky. He tells them that he will take them to someone who can help them mend the broken star, none other than Santa Claus himself.
CHAPTER 22: Santa makes the group welcome and orders up his reindeer to take the four adventurers to the shop of Jack Frost, who quicker than quick, repairs the Silver Star as good as new. He puts it on his window sill to get good and cold, but when they are ready to go, they find it missing!
CHAPTER 23: Jack Frost raises the window in time to spot the Bad Dolls dashing away with the star. Santa orders out the detachment of tin soldiers to pursue the dolls. But bad news, Captain Tintop radios back that the troops are encountering difficulties. A strange creature, never before seen in the Snow Country, is aiding the Bad Dolls.
CHAPTER 24: Back in Santa's office, things become clear. Melissa has warned that Wintergreen has escaped from her exile and has headed for the Snow Country. Reinforcements are sent to the soldiers battling the witch. In the meantime, Santa takes his visitors on a tour of the North Pole workshop. Then comes word that Capt. Tintop has returned victorious… and with the star!
CHAPTER 25: It's nearly Christmas now and the intact star is back with Judy and Jimmy. They are anxious to return to their home. Crazy Quilt wants to remain at the North Pole, but the children and Paddy are to return in Santa's sleigh. Jimmy asks Crazy Quilt to hold the star as he climbs up into the sleigh. When he turns to ask the dragon to hand him back the shiny ornament, our friends discover he's gone... running away as fast as he can!
CHAPTER 26: In Santa's sleigh, the all set out in hot pursuit after Crazy Quilt, who is headed straight for the North Pole. If the dragon can climb the pole to where the Misty Folk live, he will escape forever with their precious star. Paddy clutches the dragon frantically, then, in an inspiration, hollers a loud 'boo!' Crazy Quilt tumbles down the Pole. There is a wild scramble and... The children suddenly hear Mother's voice saying, “Wake up! You're all tangled up in that old crazy quilt coverlet.” Mother doesn't understand, of course, and Judy and Jimmy wonder to themselves, was it all really a dream? In gratitude to Paddy O'Cinnamon for his help, they vow to find the little stuffed bear a place on their tree every year. As the final chapter ends, they hear the feisty little fellow singing his song.