In The Simpsons Skateboarding, players take the four members of the Simpsons family plus Otto, Chief Wiggum, Professor Frink, Nelson and Krusty the Clown to ten skating locations around Springfield. Gameplay is similar to the Tony Hawk series, though the trick system is slightly different with some moves involving Street-Fighteresque quarter rolls of the d-pad. Each level has three kinds of objectives. Skillz school mode has challenges that involve doing specific tricks. There are five untimed goals and a final timed goal in each level. At first it serves as a tutorial of sorts, but it gets difficult later on. In skatefest, players are assigned five goals per level. Each level has one goal where you spell a word, one where you collect items, one where you find clocks in something similar to a checkpoint race and two miscellaneous goals. The final mode is a timed trick contest mode, where the objective is to get a given score within a time limit. All of these modes earn money, which is used to upgrade the characters' skating abilities. There are also various secret items to find or to unlock by completing objectives.