The first Italian Fest was organized as a Columbus Day Promotion for downtown merchants in 1984. Social, church and civic organizations from the area set up booths on Main Street to serve a variety of authentic Italian foods. Early fests featured a bocce ball tournament, entertainment, grape stomp, wine making, pizza and spaghetti eating competitions.

In 1986, a citizen group replaced the downtown merchants as festival organizers and added such popular features as bed races and the city's largest parade.
Since 1987, the Fest has come under the auspices of Collinsville Progress Inc., a civic organization and arm of the Chamber of Commerce. In 1988, the Fest was moved to mid September to take advantage of generally better weather conditions.

The Italian Fest now includes such features as the Paisan Pedal Push, 5K Run-Walk, continuous entertainment on two stages with authentic Italian Bands and local performers, Fest Olympics, Italian Cooking Contest, Bocce Ball, Grape Stomp, Wine Garden, Craft Fair, Wine Making Contest, Window Decorating, Little Miss and Mister Italian Fest Pageant and Pony Rides in the FREE Children's Area.