Research on school recess has highlighted the need for more integrated and situated knowledge of students' recess experiences as a function of school and recess context. This study assessed differences in recess-specific negative affect; enjoyment and opportunities (indoors and outdoors), and physical activity and moderate-to-vigorous physical activity (MVPA) during outdoor recess as a function of victimization, developmental level (grades 4-6 or 7-8), and school urbanization (Greater Toronto Area) or in a small more isolated city or town within southwestern Ontario, Canada. Online surveys were completed during school by 445 students (209 boys; 236 girls) in grades 4-6 (n = 266) and 7-8 (n = 179) in 11 government-funded schools (four public in the GTA and seven Catholic in smaller cities and towns). MANOVA results revealed main effect differences by recess victimization, developmental level, and school urbanization, Students reporting victimization had significantly higher negative affect; lower recess, physical activity, MVPA, opportunities, and enjoyment in outdoor recess; and lower opportunities for play during indoor recess. Students attending school in the Greater Toronto Area were significantly higher in negative affect for recess and in enjoyment and opportunities for play during indoor recess. Finally, students in grades 4-6 were statistically higher than those in grades 7-8 in each of the measured variables except for negative affect. These findings help illuminate specific insight into the potential role of victimization, recess location (indoors or outdoors), developmental level, and school urbanization on students' school recess experiences.