If we compare elementary and secondary school classrooms today with their grammar school predecessors of the Middle Ages, we might find few similarities. The terrifying image of the medieval schoolmaster, seated in a chair with his birch in hand, ready to strike supplicant schoolboys for incorrect answers, does not match our more recent and comforting portrait of the teacher who circulates throughout the classroom and nurtures students through a student-centered curriculum. Yet, as an educator trained as both a medievalist and a high school English teacher, I am regularly provoked by the affinities I discover in medieval and modern pedagogies, particularly in their prevailing theories of knowledge acquisition and perspectives on the role of the writing instructor. In fact, the romantic conception of a teacher who creates a community of writers in the classroom by sharing her own writing and encouraging her students to make meaning through writing is firmly rooted in premodern notions of textual production and grammar school teaching practices. Medieval schoolmasters such as Bernard of Chartres, Geoffrey of Vinsauf, and Robert Henryson are striking examples of teachers who not only endorsed active learning, but also established the groundwork for the “workshop” model of writing instruction and other “modern” pedagogies. In particular, I want to demonstrate the way that premodern teaching methods have informed progressive educational movements such as the National Writing Project (NWP), which has been credited for developing the philosophy that the best teachers of writing should be writers themselves.