In this review I examine the role of play and assessment in the lives of young children. These two seemingly opposing constructs are first defined. Next, I address a particularly important form of assessment, “high stakes” assessment, and argue that if it must be used, we should use a variety of assessment methods. One such method that I discuss in great detail is the use of direct observations of children's play. Examples of reliable and valid inferences about children's social cognitive functioning made with this family of methods are provided. Two specific observational instruments (one for observing play in the classroom and one for observing play in the playground) are presented. Recommendations for their use by practitioners are made.