Miss Monticello and Miss Monticello's Outstanding Teen Scholarship Organization is an official preliminary to Miss Kentucky and Miss Kentucky's Outstanding Teen Scholarship Organization. This pageant is also home to the Miss Wayne County Are Scholarship Competition.
The Miss Monticello Pageant was held for the first time in 1996. Since that time the pageant has grown each year by leaps and bounds. The first Miss Teen Monticello was chosen in 1998. In 2003 the first Little Miss Monticello Pageant was conducted with winners selected in five age categories. 2005 marked the first ever Miss Wayne County Area.