The paper reports on a study of young children and the nature of their art learning based on the in-depth approach and in the context of "chorotopos" (space-place, area, landscape, region, village or town). The sample includes 50 children drawn from three classrooms in three early childhood settings in the area of Thessaloniki and Chalkidiki, Greece. Classroom observation notes, audio-taped analysis, photographic material and the artworks of children were used to find out the influences of the programs to young children's art learning. Findings indicate that artistic activities in relation to their "chorotopos" and in-depth exploration of materials made children more situated to their own environment and enabled them to understand the potential expressiveness of materials and their inherent meaning. Teachers' role was decisive in providing special "scaffolding" to further the exploratory process in an interactive environment of learning. The findings highlight the significance of learning in, through and about art by allowing children to experience their personal environment through objects and materials encountered in their "chorotopos," to appreciate its richness and to see themselves as part of it.