This book examines the pedagogical encounters within children's ecological and socio-cultural historical contexts, and aspects of playful learning and development within these contexts. It addresses research and practices varying across learning contexts, providing easily adaptable exemplary practices leading to children's positive learning and development. The book offers a unified general cultural-historical theoretical model for exploring new contexts at different stages of children's learning and development. It suggests studying contexts as a source of development, as social situations of development. It analyzes play, early learning and the transition from play to school learning. It also explores the role of teachers and parents in supporting the development of executive functions, digital literacy, creative inquiries, problem solving and creativity as necessary and important prerequisites of children's school academic achievements. This volume contributes to the discourse on how children's learning is shaped in the 21st century era. It equips educators and parents with new and effective methods of creating developing contexts in their daily practice and to fully utilize the developing potential of existing contexts.