In the article the need of studying and of retrospective research of the issues of social education of children and youth in the pedagogical legacy of S. Shatskiy, a famous teacher, practitioner of extracurricular activities, initiator and founder of experimental education institutions, from the viewpoint of the new social-pedagogical positions is proved. The main stages of the activities of the prominent researcher and teacher-practitioner during the period from 1905 to 1932 were defined and analysed. The ways of using experience in the present-day period regarding the organization of work with children, the basis of which is the development of their activity, initiative, and independence by means of work and all-round creative action according to interests in the entertainment field, were outlined; as well as the need of an interconnection of family education, school, and pedagogization of environment and the need of an all-round enrichment of the child’s social experience etc. The contribution of S. Т. Shatsky in the development of children’s theory of the collectiveand the principle of self-government as a major in the social upbringing of children is highlighted, and the views of the scientific pedagogical value relationship to work, play, art, mental and social development of the child are considered; experimental study of the impact of physical activity on children’s collective life is conducted. On top of that, social-pedagogical aspect of the activities of S. T. Shatskiy and his colleagues was defined, i.e. the development of the content of social education of rising generation under the framework of a cleverly organised group of children that is constantly developing; education of new members of society as bearers of high spiritual culture, but at the same time work-hardened, physically healthy and capable of great endurance, determined, initiative, devoted to the motherland. The peculiarities of teacher’s development in line with the environmental approach to parenting as a task of social education of children in the era of social transformation are outlined.