Stilgoe holds a joint appointment in the Harvard Faculties of Arts and Science and Design. He offers courses on the history and future of the North American built landscape.
Author of What Is Landscape? (2015), Old Fields: Photography, Glamour, and Fantasy Landscape (2014), Train Time: Railroads and the Imminent Reshaping of the United States Landscape (2007), Landscape and Images (2005), Lifeboat (2003), Outside Lies Magic (1998), Alongshore (1994) and other books, Stilgoe is a Fellow of the Society of American Historians and winner of the Parkman Medal (1983, for his Common Landscape of America), the ASLA Williams Medal, the AIA Medal for collaborative research, the Cabot Fellowship Prize, and other awards. Among his research projects are a book on elites and another on the enduring meanings of Spanish, French, African-American, Portuguese, Canary Island, and related Creole landscape terms north of Haiti and Cuba. He restores and sails antique boats.