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 9U Wins Bay State Title

August 27, 2020

Winchester takes down Reading, 9-2, to win Baystate 9U Championship Winchester cruised to an easy victory over Reading 9-2 on Friday night to capture the Baystate 9U championship. Winchester fired up the offense in the first inning, when Ben DeChristoforo singled on a 1-0 count, scoring one run.  River Maclin was on the pitcher’s mound and earned the…

Winter Clinics Underway

March 4, 2020

Our 2020 Program starts with our Winter Clinics. These sessions are a great way for your players to stay active and start preparing for the season ahead! To participate, you must be registered with SYBS for the upcoming Spring season. To register for the season and the Winter Clinics, click below.

SYBS Scholarships Awarded

March 4, 2020

SYBS is proud to announce the recipients of the SYBS Scholarships for 2018. Rebecca Melaragni and Teddy Falkenberg were chosen from a group of highly qualified applicants to receive scholarships of $1000.00 each as they embark upon their collegiate careers this fall. They will be attending Merrimack College and UMass Amherst, respectively. The SYBS Scholarship…

WYBSGear copy
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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