Field trips to museums and performing arts centers are not a frequent activity for most students, so how do cultural organizations learn to make the most of these limited but potentially valuable "gateway experiences" toward increased arts participation? This cross-sectional study examines the engagement of students during a performance at a performing arts center with data collected over three seasons of performances across art forms, grade levels, and student populations (students who attend Title I schools, English learners, and students with disabilities) under the umbrella of Positive Youth Development theory. The findings of regression analyses and analyses of variance feature three aspects that may optimize positive engagement in the arts experience for students: prior attendance to performances, lessons in the art form, and preparation prior to the performance. However, when the data is disaggregated by priority populations, not all the factors predict higher positive engagement in a statistically significant way. The feature that may have a consistent incidence across all populations, and exclusively for students with disabilities, is preparation prior to the performance. These results present practical implications for audience recruitment, accessibility supports, and learning design for diverse learners.