It is put on by the Cumberland Farmers' Club and is usually held the last week in September.

The annual Maine State Pumpkin and Squash Weigh-Off is held at the fair.

An adult is limited to one entry in the giant squash and pumpkin weigh-off.

[2] The inaugural Cumberland Fair was held for two days, on October 10 and 11, 1868 in the center of town in the back of what is now Greely Junior High School.

On show were foods, handicrafts, vegetables of all shapes and sizes and also steers, especially in the traditional ox-pull.