Softball | 14U


Winchester Youth Softball as of 2020 is broken up into 3 seasons. Each season serves a different need and the ability to participate in one or all three seasons is available for all softball players.

Spring League Dates: 

Pre-Season: Jan 7, 2023

Regular Season: Games begin the week after April vacation baring weather.


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 to try to avoid conflict with high school softball games and have a start time 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.

Tournament Team

This year WYBS will be placing a 14U team into the Babe Ruth World Series Tournament Bracket. Practices for this will begin starting in Jan with games Babe Ruth softball tournament play starting the middle of June with the State Tournament. Winchester is looking to potentially host the State Tournament at one of our fields. The New England Tournament will be held in Londonderry NH from June 28th- July 2nd. The Babe Ruth World Series will be in the middle of July and is a week long round robin tournament with quarter, semi and finals to crown a champion. In past years this tournament has been hosted by Plant City Florida. More details to come on this as we know more.


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