Act 1

The narrator (Jeff Newman) introduces four groups of characters: Cinderella (Taylor Rammer), who wishes to attend the king's festival; Jack (Joshua Kaiser), who wishes his cow, Milky White, would give milk; a baker (Michael Angelo) and his wife (Jaclyn Freeberg), who wish to have a child; and Little Red Ridinghood (Lilly Picha), who wishes for bread to bring for her grandmother (Sara Rislov).

The baker's neighbor, an ugly old witch (Sara Buckholtz), reveals the couple is infertile because she cursed his father for stealing her vegetables, including magic beans, which prompted the witch's own mother to curse her with age and ugliness. The witch took the baker’s father’s child, Rapunzel (Chelsea Peters). She explains the curse will be lifted if she is brought four ingredients—"the cow as white as milk, the cape as red as blood, the hair as yellow as corn, and the slipper as pure as gold"—within three days. All begin the journey into the woods: Jack to sell his beloved cow; Cinderella to her mother's grave; Little Red to her grandmother's house; and the baker, refusing his wife's help, to find the ingredients ("Prologue").

Cinderella receives a gown and golden slippers from her mother's spirit ("Cinderella at the Grave"). A mysterious man mocks Jack for valuing his cow more than a "sack of beans". Little Red meets a hungry wolf (Edward Doerr), who persuades her, with ulterior motives, to take a longer path and admire the beauty of the woods ("Hello, Little Girl"). The baker, followed by his wife, meets Jack. They convince him that the beans in the baker's father's jacket are magic and trade them for the cow; Jack bids Milky White a tearful farewell ("I Guess This Is Goodbye"). The baker has qualms about their deceit, but his wife reassures him ("Maybe They're Magic").

The witch has raised Rapunzel in a tall tower accessible only by climbing Rapunzel's long, golden hair ("Our Little World"); a prince (Derek Anderson) spies Rapunzel. The baker, in pursuit of Little Red's cape ("Maybe They're Magic" Reprise), slays the wolf and rescues Little Red and her grandmother. Little Red rewards him with her cape, and reflects on her experiences ("I Know Things Now"). Jack's mother (Nancy Misch) tosses aside his beans, which grow into an enormous stalk. Cinderella flees the festival, pursued by another prince (Edward Doerr), and the baker's wife hides her; asked about the ball, Cinderella is unimpressed ("A Very Nice Prince"). Spotting Cinderella's gold slippers, the baker's wife chases her and loses Milky White. The characters recite morals as the day ends ("First Midnight").

Jack describes his adventure climbing the beanstalk ("Giants in the Sky"). He gives the baker gold he stole from the giants to buy back his cow, and returns up the beanstalk to find more; the mysterious man (Jeff Newman) steals the money. Cinderella's prince and Rapunzel's prince, who are brothers, compare their unobtainable amours ("Agony"). The baker's wife overhears their talk of a girl with golden hair. She fools Rapunzel and takes a piece of her hair. The mysterious man returns Milky White to the baker.

The baker's wife again fails to seize Cinderella's slippers. The baker admits they must work together ("It Takes Two"). Jack arrives with a hen that lays golden eggs, but Milky White keels over dead as midnight chimes ("Second Midnight"). The Witch discovers the prince's visits and demands Rapunzel stay sheltered from the world ("Stay with Me"). Rapunzel refuses, and the witch cuts off Rapunzel's hair and banishes her. The mysterious man gives the baker money for another cow. Jack meets Little Red, now sporting a wolfskin cape and knife. She goads him into returning to the giants' home to retrieve a golden harp.

Torn between staying with her prince and escaping, Cinderella leaves him a slipper as a clue ("On the Steps of the Palace") and trades shoes with the baker's wife. The baker arrives with another cow; they now have all four items. A great crash sounds, and Jack's mother reports a dead giant in her backyard. Jack returns with the harp. The witch discovers the new cow is useless, and resurrects Milky White, who is fed the ingredients but fails to give milk. The witch explains Rapunzel's hair will not work, and the mysterious man offers corn silk instead; Milky White produces the potion. The witch reveals the mysterious man is the baker's father, and drinks the potion. The mysterious man falls dead, the curse is broken, and the witch regains her youth and beauty.

Cinderella's prince seeks the girl who fits the slipper; Cinderella’s desperate stepsisters (Sara Nash, Erin Wieser) mutilate their feet ("Careful My Toe"). Cinderella succeeds and becomes his bride. Rapunzel bears twins and is found by her prince. The witch finds her, and attempts to claim her back, but the witch's powers have been lost in exchange for her youth and beauty. At Cinderella's wedding, birds blind her stepsisters, and the baker's wife, now very pregnant, thanks Cinderella for her help ("So Happy" Prelude). Congratulating themselves on living "happily ever after", the characters fail to notice another beanstalk growing.

Act 2

The narrator continues, "Once upon a time... later." Everyone still has wishes—the baker and his wife face new frustrations with their infant son, newly rich Jack misses the kingdom in the sky, Cinderella is bored with life in the palace ("So Happy")—but is relatively content.

With a tremendous crash, a giant's foot destroys the witch's garden and damages the baker's home. The baker travels to the palace, but his warning is ignored by the prince's steward and by Jack's mother. Returning home, he finds Little Red on her way to her grandmother's; he and his wife escort her. Jack decides to slay the new giant and Cinderella investigates her mother's disturbed grave. Everyone returns to the woods, but notices that the weather is more ominous ("Into the Woods" Reprise).

Rapunzel, driven mad, also flees to the woods. Her prince follows and meets his brother; they confess their lust for two new women, Snow White (Laken Buckholtz) and Sleeping Beauty (Hannah Bockenhauer) ("Agony" Reprise).

The baker, his wife, and Little Red find Cinderella's family and the steward (Hunter Kroll), who reveal that the giant set upon the castle. The witch brings news that the giant destroyed the village and the baker's house. The giantess (Sara Rislov)—widow of the giant Jack killed—appears, seeking revenge. As a sacrifice, the group offer up the narrator, who is killed. Jack's mother defends her son, angering the giantess, and the steward silences Jack's mother, inadvertently killing her. As the giantess leaves in search of Jack, Rapunzel is trampled ("Witch's Lament").

The royal family flee despite the baker's pleas to stay and fight. The witch vows to find Jack and give him to the giantess in exchange for her powers so she can become immortal, and the baker and his wife split up to find him first. Cinderella's prince seduces the baker's wife ("Any Moment"). The baker finds Cinderella and convinces her to join their group. The baker's wife reflects on her adventure and tryst with the prince ("Moments in the Woods"), but stumbles into the giantess's path and is killed.

The baker, Little Red, and Cinderella await the return of the baker's wife when the witch arrives with Jack, found weeping over the baker's wife's body. The baker turns against Jack, and the two, along with Cinderella and Little Red, blame each other for the situation before the four turn on the witch ("Your Fault"). Chastising their inability to accept their actions' consequences, the witch throws her remaining beans, thereby regaining her powers. The witch places one last curse on the quartet (revealing the giantess's destruction of their land), then uses her regained powers to go into hiding ("Last Midnight").

Grief-stricken, the baker flees, but is convinced by his father's spirit to face his responsibilities ("No More"). He returns and forms a plan to kill the giantess. Cinderella stays behind with the baker's child and confronts her prince over his infidelity. He explains his feelings of unfulfillment and that he wasn't raised to be sincere, and she asks him to leave.

Little Red discovers the giantess has killed her grandmother, as the baker tells Jack that his mother is dead. Jack vows to kill the steward but the baker dissuades him, while Cinderella comforts Little Red. The baker and Cinderella explain that choices have consequences, and everyone is connected ("No One Is Alone").

The four together slay the giantess, and the other characters—including the royal family, who have starved to death, and the princes and their new paramours—return to share one last set of morals. The survivors band together, and the spirit of the baker's wife comforts her mourning husband, encouraging him to tell their child their story. The baker begins to tell his son the tale, while the witch returns to lecture the survivors with a final lesson: "Careful the things you say, children will listen" ("Finale").