The stone gates at the entrance of Community Park were built in 1923, the first year of the fair at the athletic grounds. Fieldstones were collected by the Fair Board and members of the community and used to construct the gates. These gates still stand today at the entrance on Winchester Road.

Over the next few decades, the fair grew to be a two-day event and included softball, lacrosse, and football games. Originally held on May 24th, sometime around 1940 the day of the fair was changed to the first weekend in June in hopes of better weather for the event.

The construction of the Brooklin Memorial Arena in 1948-49 allowed for new indoor classes and events to be included in the fair. New events included preserves, canning, crafts, sewing, and horticulture shows.

During the 1970s, the fair expanded to become a three-day event and included a horse pull event and square dancing. In 1976, the Miss Brooklin Spring Fair Pageant crowned its inaugural queen, Sharon Rice.

By the 1980s the fair had grown even further: it became a four-day event and introduced a midway and demolition derby. The midway was established in partnership with Albion Amusement in 1985 and still continues today.