Grassroots organizations have a critical role in supporting learning within many urban communities (Sobeck, Agius, & Mayers, 2007). Unfortunately, many informal organizations are short-lived as funding disappears and volunteer participation wanes. The Unspun Heroes, an informal fibre arts group committed to learning and developing skills related to local fibre arts culture, has been in existence so long that when queried, the members could not easily determine its origins. Through an exploration of 16 Heroes' experiences over the course of one year, it was determined that the Heroes community is sustained, supports learning, and survives at least in part because its organization mirrors that of an informal community of practice (CoP), which supports local community cohesion, intergenerational learning, and positive community action. In this research, the roles and responsibilities of the members within the CoP, as well as the characteristics of the CoP, are discussed with the aim of presenting key factors that support sustaining CoPs for informal learning and well-being. We identified six factors characterizing the CoP that contributed to its longevity: adherence to tradition, stress-busting, social connections, mentoring space, belonging to something bigger, and sharing. Each of these is discussed in relation to the current literature and community context. Finally, from these factors, we share three important considerations for adult learning design for well-being.