The company enters, waves and begins to assemble the set and put on costumes. The Storyteller comes forward and welcomes the audience to the story of Rapunzel – a musical fairy tale, complete with Wicked Witches, Heroic Princes, Kings, Magic and the longest hair in the world ("Once upon a Time"). Once upon a time, there was a poor Cobbler who lived with his Wife. They were both very hungry and lived next door to a beautiful garden. Unfortunately, the garden didn't belong to them; it belonged to a grumpy Witch who was very proud of her vegetables. She refused to share anything from her garden with the Cobbler and his Wife.

One night, the Cobbler and his Wife are so desperate for food that the Cobbler goes to the Witch's garden, gathers as much food as he can carry and tries to sneak back home. Unfortunately, the Witch catches him and, although she doesn't punish him, she tells him that he can take the food on one condition: she gets to keep his first born child. Confused by hunger, he agrees to this.

Three years later, the Cobbler and his Wife have a baby girl, but before they are even able to give her a name, the Witch comes and takes her from them, naming her Rapunzel. She takes the baby far from her birthplace and keeps her in a tower, where the child grows, unaware that the Witch is not her mother.

Rapunzel grows up in the tower, and the only person who visits her is the Witch. Every morning, the Witch comes to the foot of the tower and calls up, "Rapunzel, Rapunzel, let down your hair!" After Rapunzel lets down her hair, the Witch climbs up for a visit.

The Witch made Rapunzel a promise that she could go outside when she turns sixteen. On this special day, the Witch bakes Rapunzel a special cake and comes to pay her daughter a visit ("Happy Birthday"). Rapunzel is terribly excited at the thought of finally being able to go outside by herself, but, the Witch breaks her promise and tells her that she can have anything else but this. The Witch is going to keep Rapunzel in the tower forever.

That very same day, Prince Brian is riding through town, not far from Rapunzel's tower. It is revealed by Simon, his valet, that the Prince is running away. He feels that he is a failure, having reached the age of seventeen without doing one heroic deed ("I'm Never Going Home Again").

Once the Prince finishes his lamenting, he hears Rapunzel in the tower, singing about her current situation. Prince Brian sees this as his big chance to do something heroic at last. He then sees the Witch calling up to Rapunzel and then climbing up her hair. He realizes that the situation is indeed even more perfect than he first thought.

A short time later, Rapunzel is alone inside the tower when Prince Brian calls for her to let down her hair. Without even thinking, Rapunzel tosses her hair out of the window, and after a moment, Prince Brian swings himself up over the ledge. He tells Rapunzel to collect her things so that he can rescue her from the evil Witch, but she isn't sure what he is talking about. The only other person whom she knows is her mother, and she certainly can't be a Witch. The Prince, thinking he has made a horrible mistake, starts to go, but Rapunzel stops him by offering him a piece of her birthday cake. He eats a piece of cake with her and then learns a bit more about the girl. She spends her time completely alone with her hair ("Me, My Hair, and I").

The Prince then tells her what it is like to live in the real world. Oddly enough, he doesn't have a lot of friends, since his father is very particular about the people with whom he associates. Rapunzel tells Prince Brian that he had better go before her mother returns, but before he climbs down her hair, he promises to visit her some time soon.

The very next morning, the Prince wakes Simon and drags him back to the middle of the woods. He just has to see Rapunzel and wants Simon to keep watch. If the Witch shows up, Simon has to stop her from coming up the tower. With that said, the Prince calls to Rapunzel and climbs up her hair while Simon stands guard. No sooner is Prince Brian up inside the tower than the Witch approaches and Simon is forced to stop her. He tries a variety of things to get her out of the way and is finally forced to dance with her and tell her just how beautiful she is ("Wooing a Witch"). Once he sees that Prince Brian has climbed back down the tower and is safely out of sight, he prepares to go. However, by this time, the witch is completely enchanted with Simon and wants a kiss. She gets what she wants before letting him go.

The Prince visits Rapunzel every day, so Simon keeps the Witch busy every day. After some time, the Witch is completely transformed from an evil woman into a lovesick schoolgirl. Up in the tower, Prince Brian shows Rapunzel all of the many things that she can only see in the outside world: a kite, a helmet for jousting, a wooden recorder, which he teaches her to play. Hearing music for the first time makes Rapunzel wants to go outside and hear a symphony play at the castle. Prince Brian finally convinces Rapunzel to let him rescue her, even though she is worried about what the Witch might do to both of them.

The Prince tells Simon that as soon as it is dark, they will use ropes and ladders to get Rapunzel down the tower. The tricky part will be making certain that the Witch doesn't follow them. The way to do this is by having Simon make a date with the Witch and not show up. This way, the Witch (who is now completely infatuated with Simon) will wait for him at her home while Rapunzel is rescued. Simon does just as the Prince has told him but feels quite guilty; he rather likes the Witch (or Gretta as he is now calling her) and doesn't want her to be made to feel the fool ("Tonight's the Night"). While the Witch prepares for her big night (her first date ever), the two men go off to rescue Rapunzel. Unfortunately, the Witch realizes that she doesn't have her magic ring and goes off to search for it.

Her search takes her to the tower, where Rapunzel is nervously awaiting the Prince. The Witch finds the ring in the tower just as the bell tolls eight o'clock, and just before she leaves the tower, the Witch hears Prince Brian call to Rapunzel. The Prince climbs up with Simon. The Witch then realizes that she has been duped. She is furious and puts a spell over Simon, freezing him solid. Rather than freeze Prince Brian, the Witch decides to have a bit more fun. She takes out her magic ring and turns it, prepared to punish both Rapunzel and the Prince.

The scene shifts to the woods outside of the tower, just before dawn. Rapunzel and Prince Brian are trying to find their way. On the Prince's face are a pair of metal glasses with lenses that are completely black. He struggles to remove them but can't get them off. This is the spell that the Witch has put over the Prince, and unless she undoes it, he's going to stay this way forever. Rapunzel doesn't know what to do but suggests that maybe they try to get to the castle. She's never been outside, so she doesn't know where to go. Not being able to see makes it impossible for the Prince to lead her, but Rapunzel is convinced that they have to try, at least. She gathers up her hair and tries to describe the different sights that she see as Brian tells her which way to go ("The First Step Is the Hardest").

After a rather shaky start, they finally reach the town and knock on the door of the inn. They are very hungry and ask the innkeeper for some breakfast, but he wants money that they don't have. The Prince tries to tell him who he is, but the glasses keep him from being recognized. The innkeeper tells Rapunzel that by selling her hair to the wigmaker, they could get enough money for breakfast. Seeing no other way out of this, Rapunzel and the Prince go to the wigmaker's shop and have her hair cut off. For that, they are giver ten pieces of silver.

Before getting breakfast, the Prince suggests to Rapunzel that she find a carriage that can take them back to the castle. Rapunzel leaves the Prince alone and goes off to find a carriage. She talks to a man who is mopping the floor and asks him to help her. Seeing that she doesn't know what she is talking about, the man takes her ten pieces of silver in exchange for his mop, which he tells her is a carriage. He tells her that by putting one leg over it, the carriage will take her wherever she wants to go. Rapunzel takes the mop and excitedly returns to the Prince and shows it to him. He informs her that she has been duped, also telling her that she needs to be careful, since certain people just aren't nice. Now, they have to walk to the castle, making their way through the Haunted Forest.

When they finally arrive at the castle, they knock on the gate, and a guard comes to talk with them. At first, he doesn't recognizing the Prince, but after some persistence from Rapunzel, he agrees to let them see the King.

The King recognizes his son and wonders where he got the ridiculous glasses. Prince Brian introduces Rapunzel to his father and tells him the entire story. The King tries to remove his son's glasses but realizes that he can't. He then thanks Rapunzel for all of her trouble and asks her to leave. Prince Brian, of course, has other plans and wants Rapunzel to stay. The father and son fight about this as the Witch appears. She hopes that her daughter has finally come to her senses and is ready to come home, but Rapunzel has no intention of returning to the tower. Both the King and the Witch wonder just what has gotten into their children ("Growing Up"). Rapunzel and the Prince plead their case, and the King and the Witch eventually let them have their way. The King lets Rapunzel stay at the castle. The Witch breaks the spell of the glasses. The two lovers are as happy as can be... when they realize that Simon is still in the tower.

They rush back to the tower and call to Simon. Oddly enough, he doesn't sound very panicked, telling them that there is no rush to get him down. He appears at the window with the Witch. It is a happy ending for everyone.