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 10s Rolling in Bay State Tournament

August 2, 2021

On July 21st the Winchester 10U Bay State team captured first place in Round One of the Bay State Baseball Tournament Champions. The undefeated 8-0 Winchester team faced a fired-up Belmont squad intent on avenging two previous tournament losses to Winchester. Starter Jack Silberhorn threw four strong innings with seven strikeouts. With the score tied…

Mudcats Win AA Championship

June 17, 2021

Anchored by strong pitching from Sean Garrity, Jack Usera, Max Wilcken and Moby Meyers, The AA Mudcats were able to live true to their name and manage a victory amidst some very wet conditions Monday night. Bryce Shaw fired three shut-out innings for the Raptors, while Cooper Statires and Jack Doherty anchored the catching spot amidst…

Winchester 12U Softball Champs 2021 – A Perfect Season!

June 14, 2021

Winchester Red 12U capped off an undefeated season on Sunday, June 13, 2021, against a tough Arlington team to win the championship. Arlington got off to a great start, jumping out to a commanding 6-1 lead through the top of the third inning. Winchester battled back with three runs in the bottom of the 3rd…

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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