In this paper we draw on Mettler's concept of the "policyscape" and apply it to an examination of policy-making processes and "events" as they pertain specifically to an analysis of transgender inclusivity and gender diversity in the Ontario context. We employ Ball's focus on policy as text and policy ensembles alongside Bailey's employment of "policy dispositifs" to map key "events" that characterize important legislative developments that define the Ontario education policy landscape with regards to addressing gender identity and gender expression as a basis for anti-discrimination. We situate particular "events" such as the GSA (Gay Straight Alliance or Gender and Sexuality Alliance) and sex education controversies within a broader context of trans activism, which we identify as pointing to quite specific contingencies that characterize the Ontario "policyscape". Overall, the paper extends a consideration of the specificities of the Ontario case in Canada to a broader reflection on the utility of the "policyscape" as a crucial concept for making sense of the relevance of more general characteristics of a spatially-focused trans informed policy analysis.