This article examines the processes of knowledge acquisition and transmission among adults within two "communities of practice" in Humboldt Park/"Paseo Boricua," a Puerto Rican community located on Chicago's near-northwest side. In particular, we examine the ways in which two adult women engaged in learning processes and enacted cultural practices within their workplace settings, a community café and a local health initiative. A primary objective of this broader ethnographic study is to provide insight into the various ways that community residents obtained and utilized knowledge, skills, and practices, as well as the larger role that these spaces and sites play in the life of the community.