Providing Winchester's Youth with Quality Baseball and Softball Leagues for All Ages

Our mission is to provide a quality baseball program for the youth of Winchester.  The organization strives to provide players with the opportunity to develop their baseball skills within a fun and competitive environment.  We emphasize the values of teamwork, sportsmanship, hard work, competition and community to help develop our children into the leaders of tomorrow.


For players between the ages of 6-15, SYBS offers a competitive and fun atmosphere for children to learn the fundamentals of baseball and good sportsmanship.


For players between the ages of 6-13, our Softball program builds a strong fundamental foundation at an early age, building to more competitive teams as players mature.


Registration is now open for the 2022 Majors Baseball Season.  

Players that would like to try out for Majors must register by September 30.  

Players that were already on a Majors team in 2021 do not need to tryout but they must be registered before the September 30th deadline.


Saturday October 2, 2021 at Nutile Field.
(Rain Date is Sunday October 3 at the same times.)

10 years old: 8:00 AM – 10:00 AM
11 years old: 10:00 AM – 12:00 PM
12 years old: 12:00 PM – 1:30 PM
(Age the player will be on April 30, 2022)

Players not available at the times above but players are strongly encouraged to attend a different morning session.  Otherwise, they can attend the afternoon session 4:00 PM – 5:30 PM

All players must attend tryouts in order to be drafted.  

Game Recaps

Catch up on all the action from across the league from our team of student reporters.

Winchester 10U Summer Tournament Team Defends Bay State Title

August 15, 2021

On August 15th, the Winchester 10U Bay State baseball team successfully defended their title as the Bay State Tournament Champions against a fired up Reading Red squad! The hometown fans were wowed by an absolute gem of a game as the Winchester 10s saved their best play of the summer season for the tournament finale…

Winchester 12U Wins Gold in Bay State Trophy Weekend

August 9, 2021

The Winchester 12U team played flawless baseball this weekend to win gold in the second Trophy Weekend of the Bay State Tournament, their second trophy of the summer and first gold trophy ever! The offense scored 17 runs over the two games, while their pitchers gave up no runs and only 4 hits! In Game…

Winchester 9U Team Wins Their Second Silver Trophy

August 9, 2021

The Winchester 9u team picked up its second silver cup of the year in Trophy Weekend #2. Needing to save pitching arms for the upcoming Tournament of Champions, the team felt happy to split the weekend action and be in strong position for the coming week. In Game 1 against Concord, Max Wilcken started on…

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Show your support for the Winchester Summer Baseball Teams with some custom Winchester Baseball gear!

The Summer Orders have been placed.
If you missed out, stay tuned for the next opportunity to order!

About WYBS

Winchester Youth Baseball & Softball Association (WYBS) provides quality baseball and softball programs for youth in Winchester, Massachusetts.
Click below to learn more about our program and how you can participate.



Nutile Field is now a LiveBarn Venue.  If you can’t make it to the Field,
you can still stay connected by watching all events Live and On Demand.



Winchester Youth Baseball & Softball has partnered with HomeWorks Energy to help Winchester families save money on energy bills and reduce their carbon footprint.  Sign up for a FREE Home Energy Assessment and HomeWorks will donate $50 to WYBS!

WYBS "Grand Slam" Sponsors