The four stories provided here offer a peak into the rich and exciting world of transgender representations throughout history. The images were found in the archives at The American Antiquarian Society in Worcester, MA, a world class research library that is open to the public and has a great amount of material digitized and available through its website. The tireless Laura Wasowicz introduced me to their vast collection of children’s literature while my friend and colleague Kate Adams pointed me to the Eliza Leslie stories. This short exhibit was curated from extensive amounts of research I have done on the larger project titled, “American Transgender Histories: from Revolution to Civil War.” This research has been funded by several generous sources, including the National Endowment for the Humanities Fellowship at the American Antiquarian Society, Andrew Mellon Foundation Fellowship at the Massachusetts Historical Society, and Research Matters Grant from Connecticut College.