Benjamin is deeply interested in the confluence of empire, geography and planning, and economics in the eighteenth-century British Atlantic world, as well as in the history of urbanization. He is currently working on an analysis of the West Indian Ceded Islands between the Seven Years' War and the American Revolution, its role in the professionalization of surveyors, and the region's influence elsewhere in the globalizing Empire.
He received a B.A. summa cum laude from Tufts University, and is a 2009 national Beinecke scholar. Benjamin is sole- or co-author of a number of peer-reviewed academic articles. An elected fellow of the Royal Geographical Society, he also serves as book reviews editor for New Global Studies.