Jack Wilcox felt that Plymouth youth should have some knowledge about the history of their home town and some familiarity with historical research materials.

The Wilcox Foundation Board organized the Wilcox Essay Contest to encourage high school seniors to conduct historical research, including learning about the Plymouth Historical Museum, historical documents available at the Museum and Plymouth Library as well as other sources such as old Newspaper collections and  even older Plymouth residents.

The essays are reviewed by teachers and other judges. In addition to awards based on merit, several essays are drawn at random each year. This allows every participant the chance to receive an award because the purpose of the Contest is to encourage learning about the history of Plymouth and not necessarily provide awards to the best written papers.