This qualitative study explores the conditions of children's level of well-being and their involvement in physically active play during kindergarten outdoors time. Observations of three to five year olds from one kindergarten in central Norway were conducted. The researcher followed the children around the kindergarten's outdoors playground and across different places on a hike. Observation instruments of measuring well-being, involvement and physical activity were used for categorising the children's level in different physically active play situations. The transcriptions of video observation and field notes were examined to determine conditions creating a high level of well-being and involvement. Four examples are presented that illustrate both high and low levels of well-being and involvement in physically active play situations. The findings indicate the importance of facilitating physical play situations that create challenges, variations, autonomy and social relationships. Body language and sharing joint attention on movement experiences is probably relevant for children's high level of well-being, involvement and persistence in physical activity. The practitioner's role within physical outdoors settings is significant.