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Inspired by the abolitionist scholarship of Love (2019) and concepts of freedom dreaming within the work of Kelley (2002), this chapter explores artwork produced within a collaborative inquiry group engaging the arts and each other to create visions of a more equitable educational system. Specifically, we explore how incorporating the visual arts into a public engagement research project called Freedom Dreaming for Educational Justice provided a “portal” (Roy, 2020) through which a multigenerational group of K-12 teachers, preservice teachers and mental health counselors, and university-affiliated faculty and graduate students imagined and worked toward more just visions of education with and through the visual arts. Grounded in the principles and practices of the National Writing Project and informed by a/r/tography, this community participated in a series of arts and writing based workshops to convey their education freedom dreams. Over one year, participants created self-portraits, composed three-panel comics, imagined new worlds on plexiglass, and penned proposal postcards. Drawing on critical visual analysis methods (Rose, 2016), we analyze a grouping of artwork created by both K-12 teachers and K-12 students for a public exhibition. In our analysis, we consider both the individual pieces as well as how the juxtaposition of the artwork brings diverse perspectives on intersectional educational justice into conversation with each other and with the audience(s) viewing their art. We argue for the potential of enlisting the visual arts as conduits for collaborative inquiry and for creating contexts for intersectional justice within education.