Many people and cultures around the world celebrate the legend of Robin Hood, or someone like him. Many also celebrate the classic romance between Robin and his beloved Maid Marian. What many do not necessarily think about is the portrayal of women in the countless tales of Robin Hood, or how the historical context surrounding each tale influences its characterization of the women within them. Author after author has used this hero's life to communicate ideas and values about the relationships between men and women in their own time. Why should the context of each tale matter? I explore both the depiction and historical context of female characters in Howard Pyle's The Merry Adventures of Robin Hood (1883) and Howard Green's The Adventures of Robin Hood (1956) as a practice in what it means to think historically. Following my analysis, I put the research to work with a compilation of practical classroom implications for teachers of history, thus demonstrating the universal need and value of historical thinking and inquiry.