The first fair took place in a field near Castleton, with Fredrick Button as the first president of the Rutland County Agricultural Society.

The fair became popular enough that, in 1849, the Rutland Railroad began putting extra cars on their trains to bring people from all over Vermont and Western New York to visit.

The MSJ Green Wave Cafe is a locally run food stand at the Vermont State Fair.

The booth is run by alumni and volunteers to the Mount Saint Joseph (MSJ) Academy in Rutland, Vermont.

Other food joints at the fair sell pizza, Italian sausages, soft drinks, fried dough, corn dogs, candy apples, cotton candy, popcorn, and various fried foods.