In the wintertime, Calvin and Hobbes go down a nearby hill on their toboggan. This is used instead of the wagon, although the jokes and story lines used by both are generally similar, as are the results: almost always catastrophic. The toboggan, as is the wagon, is predominantly used in two different scenarios: profound philosophical discussions or a death-defying plunge; often these two are put together. On occasion, the toboggan's lack of any steering mechanism is discussed. Sometimes, the sled is used in place of the toboggan.
The toboggan was seen on one story arc, when Calvin and Hobbes seceded from the family and moved to the Yukon. They brought the toboggan along, intending to ride it through the snow of the Yukon, but never made it that far. Curiously, Hobbes refers to it as a sled in this story arc.
- The toboggan was the last seen vehicle in the final strip.
- On one occasion, Calvin and Hobbes try to make money to buy a new "model" of toboggan for the new year.
- The toboggan and sled probably came to be when it was winter and Calvin and Hobbes couldn't ride their wagon.
- Unlike the wagon the toboggan normally crashes instead of falling down a ravine edge.
- After each ride the toboggan is put beyond repair but comes back good as new in its next appearance.
- Calvin favors the toboggan over the sled for its lack of a steering mechanism.