Winter grew up in Hyde Park, NY and graduated from Franklin Delano Roosevelt High School in 1992, where he was a member of the varsity soccer and rowing teams. While in high school, he also represented the Hudson Valley in rowing in the Empire State Games. Upon graduation, he enrolled at Boston University where he was first introduced to rugby after failing to make the rowing team. At B.U., he was also a member of the Lambda Chi Alpha fraternity, but transferred to SUNY New Paltz after one year. There, he played rugby for the newly promoted Hawks in their first ever season in Division 1 in 1993 up until their playoff run in 1996. He then attended Northeastern University, playing rugby for the NU "Maddogs" throughout the remainder of his college career until his graduation in 1999. After college, Winter played briefly with Clontarf Rugby in Dublin, Ireland, making just a handful of appearances as a utility forward with their junior sides before the 2001 foot-and-mouth outbreak halted the majority of the 2001 rugby season. Following the lifting of the travel ban, Winter joined Bus Éireann RFC in the Leinster junior league for the remainder of their season.