Scenes of the Seasons.

There are lots of issues with shooting outside. Also you want to schedule certain things at certain times, but that may take you from one season into the next. You can fudge a certain amount of time. This is for seasonal areas rather than those that don't significantly change throughout the year.

Late autumn - winter - early spring.
If snowless, these look almost alike, though in the early-spring, buds appear on branches, but this is only noticeable in close-ups or when you have people go frame-by-frame looking for asynchronous events. If the temperatures are below freezing, it is relatively easy to make a snow-making machine and turn the scene into winter. If you need a slushy mess for a scene, late autumn and early spring allow for you to snow it at night when it is freezing, then let the morning sun make it go all slushy.

Late spring - early summer
These look similar in green leaves. Make sure that if you want certain flowers in bloom in a scene, you know when they're going to bloom and for how long in the location you're shooting.

Late summer - early fall
You can shoot some late summer for fall with the use of foral spray dyes. Quickly add color to leaves cut a some off and leave them on the ground. Instant autumn. This I noted back when they had shot the live-action Charlotte's Web and they freaked out because the corn-field had gone yellow. Spray dye green could fix this in several hours with bunch of people out there.

Late autumn - if you're shooting anywhere besides a complete evergreen forest, it will be obvious as all the trees are colored and leaves are falling.

The other thing to remember is that the sun falls at different angles through the year. High sun in the summer and low to the horizon in the winter. Also there are color temperature differences due to those angles. If you're shooting night scenes, generally the only obvious item is the moon, which is constantly changing. Also the direction / apparent size can change from night to night. Also if you're far enough from civilization, the stars might be obvious, not to mention that you have to keep on aeroplanes and satellites if they become obvious. Try to limit the times that the sun or moon is present in a shot, and when they are, try to match the angle and color by shooting them together whenever possible. Also try to shoot them as quickly as possible. If you're actors want to crack each other up on set, these are NOT the scenes to be wasting time screwing around.