Berg played high school baseball in Wisconsin for the Antigo Robins. He began his college baseball career at Indian Hills Community College in Iowa. He was selected by the New York Yankees in the 43rd round of the 2003 Major League Baseball draft with the 1,290th overall pick. He did not sign immediately. In the summer of 2003, he played collegiate summer baseball for the Wisconsin Woodchucks and won a Northwoods League championship. He then played a season of college baseball at Triton College in Illinois before signing with the Yankees.
