The goal of this dissertation is to develop a connection between poetry and teacher education. I am motivated to undertake this project because poetry is an underappreciated resource, one that has a good deal to teach teachers. Specifically, I believe that poetry can teach teachers about how to creatively and democratically respond to problems of misunderstanding that arise in the classroom. In order to show how this is the case, I focus on the work Robert Frost. An experienced teacher and teacher educator, Frost devotes significant attention--in his poetry and prose--to problems of misunderstanding. "North of Boston", his second volume, explores-- through vivid descriptions of individuals caught in conflicts--what it means to work against misunderstanding, and what it takes to create conditions that make understanding possible. Using my readings of "North of Boston" as a starting point, I work to show their explicit educational significance by developing Frost's educational philosophy. I do this by expanding my attention to include Frost's prose, and by contextualizing Frost's work within a pragmatist tradition that originates with Ralph Waldo Emerson. I show that Frost's philosophy of education is--despite surface differences that are immediately apparent--closely related to the work of John Dewey, and I argue that comparing the two thinkers creates a bridge between Frost's poetry and the world of educational research. After this bridge is established, I focus on the practical implications of Frost's work for teachers and teacher educators. [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.]