This study seeks to contribute to our understanding of the problem of effectively encouraging historical thinking by (a) evaluating, and modifying Wineburg's heuristics for historical thinking for applicability to the problem-solving activities historians use at historic sites; (b) establishing the efficacy of a hypermedia-based education program "Tories, Timid, or True Blue?" at the Old North Church in Boston, Massachusetts, for encouraging historical thinking in middle- and high-school teachers (c) determining the amplifying effect that the combination of the use of multiple documents and the historic site from which they are derived has on historical thinking. Results suggest that this combination of activities does lead teacher users to reason in ways that suggest more sophisticated historical reasoning. However, considerable attention is paid to the ways in which historians and teachers think differently about the historic sites they encounter and how the overlaps therein might be used as the foundation for encouraging effective partnerships between historians and teachers as co-equal partners in improving history education. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]