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 Season City League:

Our Spring Season will be part of a league named the City League, that includes multiple teams from Arlington, Belmont, Watertown, Brighton, and Waltham. This league will continue to build on skills but games will be player pitch only. Winchester usually places multiple teams in this league that will be comprised of Winchester players selected by the coaches.  Game days are currently scheduled for Monday- Friday with start times at 6:15 PM (subject to change) With multiple teams from Winchester, the expectation is that the majority of games will be in Winchester. Practices will be scheduled by the coach. This league is a great league for players of all skills level.

      Spring League Dates:

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

      Pre-Season Training: This is something that is new to Winchester Softball and is part of your registration fee however we understand if not everyone can make the pre-season training. This year starting on Feb 28, 2021, we will have the use of the Edge Sports Complex in Bedford MA to help teach pitching, fielding, and hitting drills prior to taking the field for the 1st game. Sessions will be held on Sunday morning from 8 AM-9 AM with your team every week (time will change for April). While participation in this is not required we would love to see if we can get as many girls there as possible. Our goal is to partner with Winchester High School players and coaches as well as Planet Fastpitch to help teach the girls the valuable skills that they will need prior to venturing outside in the late spring to make this game enjoyable for them.

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.

      Summer League Dates: TDB

Fall League (New for 2021)


      Dates: September -November 1 TBD

Register for the 2021 Spring Season today!

Spring registration deadline is March 15th.


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