During the game, each chapter takes place in a certain season.
The game starts out in fall (autumn). Most trees are with characteristic colored leaves, and some of them are seen falling on the ground. There is occasional rainfall.
Chapter 2 occurs during the later part of fall. The last mission of the chapter, Boxing Challenge, occurs just as the first snow falls.
Chapter 3 takes place in winter and all NPCs in the game change to their winter outfits. The ground becomes slippery, which affects Jimmy's handling on the skateboard and on bikes. New props that are exclusive to the Winter season can be found (such as snowmen), and the detention mini-game changes, which involves shoveling snow. Jimmy can also start snowball fights. The errand Lawn Mowing is unavailable during this season. Most trees are leafless. Most days in winter are cloudy, and there is occasional snowfall. Also, it gets dark much earlier, by around 17h30.
It is spring, and the snow is gone. The trees that lost their leaves are leafy again. Generally it is sunny, but there is the usual rain.
Chapter 5 takes place in late spring.
Chapter 6, as its name indicates, occurs in the summer. All the days are now sunny without clouds. But there's a way to bring the climatic changes back, by doing the Lawn Mowing job in the Old Bullworth Vale house. After a while, the sky will begin to get cloudy, in rare occasions it can start to rain.