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.

Summer 2024 Baseball

Registration is now open for the Summer 2024 Baseball season for all ages and levels. 

Become a WYBS Sponsor!

Participating as a sponsor of WYBS gives you and your organization the opportunity to gain outstanding visibility to the Winchester Community.
Find out how!

Spring 2024 Softball

Registration is now open for the Spring 2024 Softball season. 

Volunteers Needed!

WYBS is run by a small, dedicated group of volunteers.
There are many ways to help aside from coaching a team... if you'd like to learn more, contact us today!

Game Recaps

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

A Heavenly Performance!

October 23, 2021

Congratulations to the Angels on capturing the Fall Season Majors Championship with a 7-3 win over the Rangers. The season finale lived up to its billing with the top-seeded Angels managed by veteran coach, Steve Boksanki, taking on the second-seeded Rangers, managed by coach, Marc Grimaldi. The Rangers bats were hot as they led off…

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…



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.


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.

Follow Winchester Baseball & Softball on Instagram!


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!
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Show your support for Winchester Baseball & Softball
with some custom Winchester Baseball gear!

The shop is now closed, but will open again before the Spring Season...  Stay tuned!

WYBS "Grand Slam" Sponsors