In this article, the authors examine the potential in developing a model of curriculum design for Humanities/Liberal Arts courses in urban universities that focuses on cultural pluralism, community organizing, and collective inquiry as a means to foster university students' self-development and self-understanding as citizens, and active participants within the city. Their community-engaged approach arose as a response to the pedagogical and ethical complexities we faced as course lecturers teaching at the downtown campus of Ryerson University, which is situated in the heart of the city in Toronto, Canada. At Ryerson, they codeveloped the syllabus for, and cotaught, a first-year course in the Faculty of Art's interdisciplinary program, Arts and Contemporary Studies. They designed the course, "Introduction to the Humanities" with specific emphasis on integrating the experiences of the Toronto multicultural landscape into the classroom. In this paper, the authors reflect on two separate attempts to move learning outside the humanities classroom and into the city itself. They begin by discussing their experiences in the classroom and the perceived incommensurability between their roles as educators teaching the importance of civic engagement and the space of the classroom as separate or isolated from the rest of the city.