This paper aligns with educators and historians who argue that certain aspects of expert historical thinking are excellent tools for democratic citizenship. The paper focuses on specifically contextualized understanding of the past, as opposed to presentist attitudes, which assume the past is just like the present. It presents a framework for analyzing contextualized historical thinking about events in terms of consideration of location, the perspectives of participants, placement within the flow of time, an understanding of the cultural tools and norms of the period, and the overall climate of opinion. Based on these elements, as well as other hallmarks of educational tasks in history, the paper sketches a task analysis, based on cognitive and sociocultural approaches to mind, of a number of activity structures commonly used in history instruction and some newer computer-based activities. It relates the task analysis to an empirical study from an intervention and study of children creating a hypermedia simulation of travel on the Underground Railroad. Appended are Web page screens created by participants and source materials used. (Contains 26 references, 1 table, and 2 figures.) (Author/BT)