This qualitative study examines children’s lived experiences of play and playfulness through interviews and creative methods with 10 children aged 8–11 in a Playwork setting. Thematic analysis identified three core themes: playfulness as an internal experience; the contextual nature of playfulness; and Playwork theory in practice. Children described play as joyful, immersive, and intrinsically motivated, shaped by factors such as comfort, outdoor access, social relationships, and autonomy. They valued adult support that preserved freedom. Findings challenge narrow definitions of playfulness, emphasizing calm, solitary, and open-ended play, with implications for designing responsive, child-centred play environments.