Wishbone keeps getting interrupted while trying to take a nap, and begins thinking of the famous nap taken by Rip Van Winkle. He soon finds himself in Rip's shoes, having taken a twenty-year nap and waking to find his world turned upside down.

An intrigue involving the election for class president reminds Wishbone of The man in the iron mask. Imagining himself as Philippe, twin brother of the King of France, Wishbone must decide if he should risk everything to escape his iron mask and trade it for the king's crown.

Wishbone imagines that he is David Balfour, the young Scottish Lowlander bound for adventure in Kidnapped, the novel by Robert Louis Stevenson.

Joe and David publish a sports newsletter using new technology that will be better than the existing paper. The idea of new being better than old reminds Wishbone of A Connecticut Yankee in King Arthur's Court.

When Joe's team is in the running for the basketball playoffs, Wishbone is reminded not to judge people by size as he imagines himself as the seventeenth-century traveler, Lemuel Gulliver, whose adventures included visits to Lilliput, where people are six inches tall, and Brobdingnag, a land peopled by giants.

Joe Talbot, Samantha Kepler, David Barnes, and Wishbone are hot on the trail of an ancient Oakdale secret! They are searching for any sign of Willow Bend--an early town settlement that was destroyed by a flood many years ago. This exiting quest makes Wishbone imagine himself as Allan Quatermain, a great elephant hunter from H. Rider Haggard's thrilling adventure tale, King Solomon's Mines.