The Westport Fair was established in 1955, under the leadership of Thomas McGarr (Voc-Ag Instructor) and Harold S. Wood (Principal), along with the support of the Westport High School Committee. The purpose of the fair was to promote agriculture in the town, and to show projects that the vocational students had completed. As time went on, it became the social event of the summer with many people looking forward to its arrival each year.
