Mary Coombs Greenleaf sought to take her place among the many frontier teachers who preceded her in 1800s. However, her destination--Indian Territory--was distinctive from previous American frontiers in that it was the geographical solution to a long record of Indian eradication policy. Mary Greenleaf was fifty-six years old, having just lost her mother, and although older than many, she was similar to those women pioneer teachers whose character and personality have been portrayed in the literature and art of the West. By examining the journals and correspondence of Mary Greenleaf and three other women teachers (Ellen Whitmore, Sue McBeth, and Emma DeKnight) who went to Indian Territory, this paper examines the rich character and broad experiences of these women and how their lives compared to conventional images such as that in Paul Nesbit's poem, "Oklahoma Women Pioneer." The authors compare characteristics of women teachers in Indian Territory to those outlined in Kaufman's study who went to the Midwest and Far West. This paper investigates the extent to which frontier teaching presented a way for these women to realize professional goals and express independence, self-worth, and individualized identity, which contrasts with Nesbit's narrow portrayal of such women as strictly architects of Zion.