Book XIV of the early Japanese poetry anthology Man’yōshū (c.780s) features poems attributed to the people of Azuma [‘the Eastland’], a region roughly equivalent what is now the Kantō area. The “songs of Azuma” (J. azuma uta) in Book XIV have generally been understood as “folk songs,” including being framed as such within the Man’yōshū itself. However, not only are the azuma uta themselves a diverse group of poems which preclude an overarching characterization as “folk songs,” they are anthologized in a form that suggests an editorial hand that likely belonged to a learned individual from the capital. Through comparing the poetry of travelers from the capital who ventured to the Eastland with the poetry of Book XIV, this article centers several preconceptions about Azuma and its people that characterize its depiction in poems by both “Western” and “Eastern” poets. While travelers are more apt to take an ethnographic approach in their compositions about the Eastland, the poems of Book XIV are curated in order to create a pastoral vision of the Eastland that both collapses and highlights the distance between courtiers and Azuma people by centering the capacity of the latter to express “strong feelings” in surprisingly sophisticated voices.