Students who attend Trinity College in Hartford, Connecticut, have elected to spend their university years in one of America's most distinguished small cosmopolitan cities. Over the last two decades as the world has become rapidly urbanized, Hartford has become a critically contested site where economic poverty, environmental degradation, residential segregation, and the search for identity in the face of fluid migratory patterns pose serious challenges and provide unprecedented learning opportunities. Moreover, students studying and living in cities almost anywhere in the world learn how urbanization--by creating problems and challenges that cross national, international, and disciplinary boundaries--has begun to collapse the distinctions between the so-called First and Third worlds. Connecting their learning experiences overseas with those at home, students are better positioned to comprehend the complex world around them. In this article, the authors discuss the urban and global initiative at Trinity College that provides fresh examples for rethinking the changing relationship between study abroad and the city. (Contains 28 endnotes.)