Trumbull is a town in Fairfield County, Connecticut, United States. The population was 34,243 at the 2000 census. RelocateAmerica. com currently ranks Trumbull, the only town selected from Connecticut, as one of the top 100 best cities to live in the U.S.. Money Magazine ranked Trumbull #68 in their top 100 best places to live rankings of U.S. cities in 2007 and #77 in 2009 .