Child engagement refers to the time spent interacting with physical and social environments according to age, abilities, and a situation. The aim of this study is to assess the functioning of children in early childhood routines using engagement assessment instruments relative to the presence of developmental disabilities, age, gender, and parental characteristics within the contexts of preschool and family routines. The sample comprised 150 children aged 3–5 (AS = 4.02, D = 0.78), including typically developing children (N = 49) and children with developmental disabilities (N = 101). To assess the children’s engagement in preschool classrooms, we used the Classroom Measure of Engagement, Independence, and Social Relationships (ClaMEISR), and the Child Engagement in Daily Life Measure was used to assess the children’s engagement in family routines. The results obtained indicate a significantly higher rate of engagement in routines and activities among girls and older children. Parental characteristics associated with children’s engagement included employment and marital status. Children with developmental disabilities, compared to their typically developing peers, had lower levels of engagement in social relationships and functional independence in daily routines. The results indicate that both instruments have a high internal consistency and are thus suitable for future use in the Republic of Serbia.