Winchester Baseball is a local baseball league that is chartered by Babe Ruth Baseball. Players 4-to-12 years of age play under the Cal Ripken Division, while players age 13-to-15 play under the Babe Ruth Division.

Youth Baseball in the Shenandoah Valley started in 1952 and for over 25 years Winchester Baseball has been a huge part of developing youth athletes that have gone on to play at the High School and College levels. Winchester Baseball had the honor of hosting the Cal Ripken 10 Year Old World Series in 2011 and 2014.

Winchester Baseball has shown success not just at a local level, but has won multiple Virginia State titles and several South East Regional Tournaments sending teams to the 12 Year Old World Series in Colorado in 1991, 13 Year Old World Series in 2001, and the 14 Year Old World Series in 2009.

The success of Winchester Baseball can be seen in the induction of its President Bob  Brown in 2010 and in 2015 Winchester Baseball become only the second league in Babe Ruth South East Regional history to be inducted into the HOF.