The aim of this study is to present the varieties of changes to children’s playgrounds over the past 26 years, depicting the stages of the design process in designing playgrounds based on an adult perspective to encourage children to play more in today’s changing society. Fourteen Japanese selected works from 1992 (first issue) to 2018 (the latest issue) were chosen for analysis. By analyzing the titles, descriptions, ichnographies, photos, and critical design reviews, the form of and changes to children’s playgrounds are revealed in this paper. Results show the quantitative trends and qualitative changing patterns related to children’s play. Daily physical playing was considered crucial in the first decade of the 1900s. In the 2000s, natural education activities were given more importance, while in recent years exercise play and variety of play have been given more attention. According to the results, we have to consider not only the richness of daily playing facilities, but also the broader aspect of playability, more than just including natural elements into designs, or increasing the variety of play styles. The different ways children enjoy play and the future design trends are also discussed in the last part of the article. Changes corresponding to the improvement of technology should be made to make playgrounds more attractive for children. This study could serve as a design reference for professionals.