While Wentworth boasts many decorated military alumni, most graduates enter the private sector. The military structure develops self-discipline in cadets with varied aspirations. Wentworth's proximity to Kansas City gives cadets all the advantages of the metropolitan area. Cadet groups attend concerts put on by the Kansas City Symphony and performances by the Lyric Opera. Visits are made to the William Rockhill Nelson Art Gallery, the Truman Library, professional sport events, and dinner theaters.
Various trips scheduled throughout the school year keep cadets exposed to area culture.
Wentworth's hostess orients cadets about matters relating to social etiquette. Subjects range from proper table setting to conventional letter writing, and complement other aspects of Wentworth's education. All cadets will participate in Military Ball, a formal dance complete with a big band and battalion and company queens being crowned. Many parents and families are involved with Military Ball as it is the highlight of the spring parent's weekend. Wentworth's Quartermaster Store, located in the center of campus, provides essentials for cadets, as well as novelty items featuring the Academy logo.