At first glance, Franz Schubert’s Winterreise would hardly suggest itself for choral adaptation. The history of choral arrangements of songs from the cycle bears this out: The only song to have a major presence in choral music since the nineteenth century is “Der Lindenbaum,” which was first adapted by Friedrich Silcher in a way that emphasized its folklike, communal potential over its darker elements. Other songs of the cycle, such as “Der Leiermann,” seem to innately resist any similar treatment. This essay focuses on how the recalcitrance of “Der Leiermann” in relationship to choral arrangement colors the approaches of two recent arrangers to the song, Thomas Hanelt and Gregor Meyer; the chapter then takes into account a more improvisatory group performance of the song presented by student performers at the Universität der Künste in Berlin in December 2008. The possibility of choral or other non-solo approaches to “Der Leiermann” innately forces performers and audiences to approach the wanderer’s solitude, and the cycle’s ending, from new subjective perspectives, even as these arrangements also attractively offer nonprofessional singers a chance to grapple with Schubert’s masterwork.