Pre-Season Training | Weekly on Sat at 8AM

Pre-Season instructional training begins the first Sat in Jan and will be held at both Ryan Connoly or Stampede Batting Cages on Holton Street in Woburn at 8AM -9AM. Working with college, high school and talented program coaches, we will work with your player to teach and improve throwing, fielding, and hitting. We will flip flop between the two locations on a weekly basis to be able to maximize the space and the skill set that is being worked on for that week. Hitting will take place at the Stampede facility and fielding and throwing will take place at Ryan Connoly.

Spring Season City League

Our Spring Season will be part of a league named the City League, that includes multiple teams from Arlington, Medford, Charlestown, Belmont, Watertown, Brighton, and Waltham. This league will continue to build on skills of the players and games will be player pitch only for 10U and up, coaches pitch for our 8U players. Winchester places multiple teams in this league that will be composed of Winchester players selected by the coaches.  Game days are currently scheduled for Monday- Thursday with start times at 6:15 PM (subject to change) Practices will be scheduled by the coach. This league is a great league for players of all skill levels.

Summer Season

Winchester Youth Softball participates in the Middle Essex Summer Program. This program consists of towns all over Middlesex County and Essex County with games played Monday-Thursday at 6:15. This league is more competitive than our spring softball league, however, it is still based around having fun and enjoying the game of softball. Your practice schedule will be created at the discretion of the coaches of your daughter's team.

Fall League 

Fall ball is a great experience to play a little more softball. For our 10 and 12U programs we enter teams into the Charles River Softball League. You play a double header on Saturday morning and then are free to enjoy the rest of your weekend.