Kessel played youth hockey with the AAA Madison Capitols in his hometown of Madison, Wisconsin. An offensive standout from a young age, Kessel put up 286 points (176 goals and 110 assists) in 86 games with his AAA bantam squad in 2001–02. He followed up on that effort the next year with the Capitols under-18 team where, during the 2002–03 season, he produced 158 points (113 goals and 45 assists) in 71 games. Kessel credits former Capitols coach and 1980 U.S. Olympian Bob Suter for becoming the player he is today.