Williamson has worked as a deputy managing editor and theater critic for The New Criterion. Williamson has also worked at the Mumbai-based Indian Express Group; the Lubbock Avalanche-Journal; Journal Register Newspapers; the Institute for Humane Studies at George Mason University, where he directed the journalism and communication programs; and as an adjunct professor at The King's College. Williamson was the editor of The Bulletin, a now-defunct daily newspaper in Philadelphia.