To better understand and promote youth physical activity (PA) it is important to determine settings and characteristics that promote or influence behavior. This study evaluated the utility of a multi-method approach (accelerometers plus direct observation) to better understand youth PA at recess. A total of 100 third through fifth grade children (52 males and 48 females) wore an Actigraph accelerometer during school recess for five consecutive days in both Fall and Spring. Trained observers coded PA behaviors at the same recess periods using the System for Observing Play and Leisure Activities (SOPLAY). Overall, gender comparisons based on both instruments indicated that boys were more active than girls. MVPA levels were higher during climbing/sliding activities (40–50%) and when the activity setting was supervised and equipped (30%). Both assessments indicated that boys were more active but the contextual data from the SOPLAY indicate that differences may vary according to the environmental context.