A growing body of psychology and education research affirms the vital role of play for children’s healthy physical, social, cognitive, and language development (Almon, 2018; Weisberg, Hirsh-Pasek, Golinkoff, Kittredge, & Klahr, 2016). Playful pedagogy allows teachers to respect children’s autonomy, promote engagement, help to cultivate their love of learning, and offer support for knowledge acquisition (Weisberg, et al., 2016). However, children are experiencing fewer play-based learning opportunities, especially at school (Almon & Miller, 2011; Brown, 2016). In preschool and early elementary settings, children increasingly engage in teacher-directed academic instruction and teachers view play and learning or schoolwork as separate or dichotomous constructs (Wohlwend, 2007). Research indicates that practicing teachers report challenges meeting academic demands using play-based learning (e.g., Pyle & Danniels, 2016) with significant tensions between playful learning and current structures for teaching and learning in many schools (Mardell et al., 2016). Preservice teachers also report tensions in understanding play as learning in practice (e.g., Walsh & Fallon, 2019). These challenges and tensions create a “huge discrepancy between what we know about how young children learn and what we actually do in preschools and kindergartens,” (Almon & Miller, 2011, p. 1). How can we close the theory-practice gap (Whitenack & Swanson, 2013) through our work as teacher educators? With renewed energy around the study of play (Zosh et al., 2018) and increasing advocacy for children’s right to play (Doel-Mackaway & Colliver, 2019), we formed a community of practice (Lave & Wenger, 1991) to strengthen our individual examinations of our strategies as teacher educators and the approaches used by teachers to support and sustain playful learning in early childhood and elementary classrooms. Inspired by the Community of Practice on Play formed through the Center on the Developing Child at Harvard University we formed our collaboration to support our mission to restore play and playful learning in early and elementary education settings. In this interactive symposium, we engage in a dialogue about our roles as advocates for learning through play (Oliver & Klugman, 2004; Sluss, 2019) in our experiences with preservice and inservice teachers in Hawaii. We report on the following research 1) a narrative study that examines a new teacher’s efforts to sustain playful learning in a public elementary school classroom; 2) an autoethnographic study of play and process in art education; here, the value of the visual arts as a means to be creative, explore meaning, and excite the imagination is recognized as a vital part of the preservice teacher’s curriculum; 3) the review of the literature and examination of goals and practices related to exploration of STEM through play, with attention to developing beginning teachers’ knowledge and practice; 4) and an examination of teacher candidates’ perceptions of play through photo elicitation and semiotic analysis. By sharing our journeys with play as pedagogy to bridge the gaps between theory and practice, we aim to consider our approaches, challenges, and apparent successes to find ways to improve and increase playful learning opportunities for children.