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Abstract: The article deals with the problem of adolescent vandalism, its prevalence in the educational environment and the space of modern cities. The specific characteristics of student’s vandal activity are described, indicating the increased risks for the formation of a stable subject delinquent behavior model. An assumption is made about the possible connection between the propensity to vandalism and its motivational grounds with the adolescent’s place of residence (metropolis or small town). The empirical verification of this assumption was carried out through the ascertaining experiment, in which 177 adolescents had been observed from secondary schools of the megalopolis (Ekaterinburg) and a small town (Irbit). Data collection was carried out using the author’s questionnaire “Motives of vandal behavior”, processing was carried out by methods of mathematical and statistical analysis (cluster analysis, descriptive statistics and regression analysis). The results confirmed the presence of a high general readiness to commit vandal acts among adolescents living in a megalopolis, as well as the specific of the vandal motivational profiles among students in Ekaterinburg and Irbit. Thus, adolescents in a small town engage in destructive interactions with environmental objects, including educational ones, guided mostly by the motives of curiosity, protest and expression of their own aggression. The adolescents in the megalopolis are characterized by a more average motivational profile with the dominance of the aesthetic motive in vandal activity. The revealed patterns indicate a significant role of the environment and its conditions in the formation of teenager’s readiness to commit vandal acts, and, therefore, can be used as a basis for the development of effective preventive measures to minimize the spread of this deviation.