Berry was drafted 55th overall in the 1997 NHL Entry Draft by the Colorado Avalanche. He played the majority of his first three pro seasons in the American Hockey League with the Hershey Bears. In his first full season with Colorado, he played 57 games before he was traded to the Pittsburgh Penguins on March 19, 2002 with Ville Nieminen for Darius Kasparaitis. He did not last long in Pittsburgh, as he was claimed by the Washington Capitals in the Waiver Draft later that year.