After a “Country Dance” in the Widow Piper’s gardens, wicked miser Barnaby claims his orphaned niece and nephew, Alan and Jane, are missing at sea, leaving their fortune to him. The Widow’s son, Tom, who has loved Jane for years, sets off to find the truth. But two sailors named Gonzorgo and Roderigo support Barnaby’s story, claiming to be the ship’s sole survivors. The sailors, realizing the Widow Piper is quite wealthy, plan to woo her to share in her wealth.
Tom, searching for Jane, encounters Little Bo-Peep, who has lost her sheep (“Never Mind, Bo-Peep, We Will Find Your Sheep”). Meanwhile, Alan and Jane arrive. They have survived the shipwreck and were aided by a band of gypsies, who dressed Jane as a boy and Alan as a woman. Jane immediately sets off to catch Tom. Alan, playfully impersonating a gypsy fortuneteller, reads the Widow Piper’s palm and says the widow’s daughter, Mary, should marry a man named Alan (“Floretta”). Mary rejects several suitors (“Mary, Mary”), because her eyes are set on Alan (“Barney O’Flynn”). Oily Barnaby attempts to woo Mary with a floral bouquet, but she discards the flowers and rebuffs him. Gonzorgo and Roderigo demand payment from Barnaby, who hired them “get rid” of Alan and Jane. They assure him they succeeded by sinking his niece and nephew's ship.
Alan and Jane, now dressed appropriately, discover the bouquet intended for Mary, and Alan is furious, thinking Mary has betrayed him. He confronts her, and they end their relationship. Barnaby is appalled to discover that Alan and Jane are alive. He hires the sailors to take the siblings through the Spider’s Forest and deliberately “lose” them. Meanwhile, Mary leaves town to escape the affections of Barnaby and Alan. Jane stays and helps her siblings with their schoolwork (“I Can’t Do The Sum”). Alan and Jane, lost in the Spider’s Forest, rescue a moth from the web before resting for the night (“Go To Sleep, Slumber Deep”). The Moth, it turns out, is a queen, and the scene dreamily shifts to the Moth Queen’s Floral Palace (“Birth of the Butterfly”).
It is Christmastime in Toyland (“Hail to Christmas”), and Barnaby and the Widow have spent three weeks looking for Mary. They hire bumbling Inspector Marmaduke to locate her. Alan and Jane arrive in Toyland, where, despite their unfashionable dress, they charm the locals (“Rock-A-Bye, Baby”). The Master Toymaker distributes toys to the children, including Jill, who has fallen for the Toymaker’s apprentice, Grumio.
Barnaby offers the toymaker a great deal of money to create toys that will wound and maim children, but the toymaker refuses. Jill meets up with Alan and Jane, who are in need of new clothing. Jill offers to bring them to the Toymaker’s shop, where she works dressing the dolls. Meanwhile, Mary, under the alias “Mam’selle Elisette,” is now making dolls for the Toymaker. Inspector Marmaduke questions her, but she claims to be an accomplished journalist (“Beatrice Barefacts”). The Toymaker has created a battalion of automated wooden soldiers, but Alan and Jane damage two of them as they don the soldiers’ clothes. Grumio convinces them to impersonate the broken soldiers, which they do with great bravado (“March of the Toys”). Meanwhile, the sailors Gonzorgo and Roderigo join Inspector Marmaduke in seeking Mary.
Tom arrives at the Toymaker’s shop (“Toyland”), and delivers a summons for the Toymaker to the Court Royal. Left alone, the Toymaker secretly works on a magical charm to make the spirits of the underworld inhabit the toys at his command. Jill attempts to spy on the Toymaker to learn his plans, but instead gets tipsy and carouses with Grumio (“Gavotte”). Barnaby visits the Toymaker and catches a glimpse of Mary disguised at “Mam’selle Elisette.” Alan and Jane plan to return home by boat, disguised as toys, but Mary recognizes Alan and the two lovers reconcile. The Toymaker tries his spell again, and this time it works. The toys rise up and fatally attack their creator while Alan stands aghast. Marmaduke and his companions enter and arrest Alan for the murder (“Finale Act II”).
At the Court Royal, Tom learns that Alan has escaped capture, and Tom assures Jane that everything will be all right (“Our Castle in Spain”). Alan and Mary, traveling in disguise with Jill and Grumio, imagine what their married life will be (“Before and After”). Barnaby, with Gonzorgo and Roderigo disguised as executioners, tells Mary that Alan will be tortured and executed if she doesn’t marry him. She bitterly relents, and they marry. Jane and the children mock Gonzorgo (“He Won’t Be Happy ‘Til He Gets It”).
Alan is captured and brought before the court. His only hope for clemency is to claim “the benefit of widow”: by marrying a widow, he can escape execution. Four widows appear to take the claim, but Alan cannot do it. The Widow Piper’s children plead with her to volunteer, but she is no longer a widow: she has married Inspector Marmaduke. Gonzorgo and Roderigo, feeling sorry for Alan, offer to poison his wine so he’ll go quickly and painlessly. He agrees, but Barnaby mistakenly drinks the wine instead, dying instantly. Mary, who is now a widow, gladly marries Alan, who is consequently freed. All the happy couples join in celebration (“Finale”).
(5 female; 5 male)
Bo-Peep — a careless shepherdess
The Widow Piper — a lonely widow with fourteen children
Contrary Mary —The Widow Piper’s eldest daughter
Jane — Uncle Barnaby’s niece
Jill — who helps Jack
Tom Tom — The Widow Piper’s eldest son
Uncle Barnaby — a rich miser in love with Contrary Mary
Alan — Uncle Barnaby’s nephew
Inspector Marmaduke — of the Toyland Police
Grumio — apprentice at The Master Toymaker’s workshop
The Spirit of Oak
Roderigo — a sentimental ruffian
Gonzorgo — Roderigo’s hard-hearted partner
Hilda — maid of all work in the Piper household
Simple Simon — who is fond of fairs
Peter — who has a passion for pumpkin pie
Tommy Tucker — who sings for his supper and everything else
Jack — who does chores
Boy Blue — who wants to be a farmer
Bobby Shaftoe — who wants to be a sailor
Sallie Waters — who wants to get married
Miss Muffet — who is afraid of spiders
Curly Locks — who wants to wed a title
Red Riding Hood — who is devoted to her grandmother
The Brown Bear
The Giant Spider
The Master Toymaker — who designs the toys of the world