The opening cutscene shows Didi Pickles, Grandpa Lou, Tommy Pickles, and Chuckie Finster in the Pickles home. Didi is setting up a board game while Grandpa reads the rules, leading to the setup screen. The game includes a multiplayer option for up to four players, and it has four playable characters, including Tommy, Chuckie, Phil, and Lil. Any characters not controlled by the players are instead controlled by the game through artificial intelligence.
The main goal is to collect the most of a specific item. Stages begin with a cutscene to explain what needs to be collected, then the game begins. A spinner is used to determine how many spaces each player can move. Items can be gathered after landing on the "Search" space, which can be recognized by the magnifying glass design. Searching may lead players to find only a dust bunny, a dud item with no function, but it is the only way to acquire certain items. If a player finds the "Double Search Power" tool when searching, he/she may search twice every turn. Dil Pickles, Tommy's brother, appears when a player stops on a "Mystery" space, driving the Reptar Wagon and changing the identity of the spaces on the board. There is a hidden square option that can be turned on or off at the start screen.
Players can collect cookies, toy cards, and energy. Cookies are a form of currency that may provide opportunities for special bonuses. Non-playable characters, such as Grandpa and Tommy's dog Spike, serve as allies doing various tasks such as giving players extra cookies when they come in contact with them. Toy cards give players special abilities. One lets players turn into Reptar and travel up to five squares and stop anywhere they like, which can only be achieved normally when a "Set Spin" is selected randomly from the spinner. Toy cards can be purchased if one lands on a toy card space; which if used wisely, can stretch the limits of game play for a single turn. Energy is needed to move from one space to another in all boards excluding Reptar Rally. If one runs out of energy, they will warp to a "Bedroom" where the player can then warp to any of the main rooms instantly. There are also spaces for recovering different sleep amounts.
