Adjudicated events, including music festivals, contests, and competitions, are performance opportunities for American instrumental music programs. The purpose of this study was to examine the benefits and challenges of participating in large-group instrumental adjudicated events in three Kansas high school programs. Data analysis followed cross-case procedures for coding data, as well as strategies for trustworthiness. Select findings revealed that participants (a) valued the process of preparing for adjudicated events, (b) valued and sought out additional instructional staff as a means of enriching the process of preparation for adjudicated events, (c) identified multiple logistical challenges associated with preparing for and attending adjudicated events, and (d) identified music considerations associated with attending large-group adjudicated events. These are likely pivotal factors in attending adjudicated events and thus can help us further understand how and why adjudicated events hold an important place in the history of American music education.