Kitson began his career with non-League Hitchin Town and Arlesey Town before he joined Cambridge United in 2001 and became one of the brightest prospects in the Third Division which led to him being signed by Reading in 2003 for a fee of £150,000. He enjoyed great success with the "Royals", forming a formidable partnership with Kevin Doyle as Reading gained promotion to the Premier League in 2006. After two seasons in the top flight Reading were relegated and Kitson signed for newcomers Stoke City for a club record fee of £5.5 million.