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.

Padres Use Fast Start to Beat Dodgers 11-2

June 14, 2021

By Jack Siciliano The Dodgers and Padres played Thursday night in the second round of the playoffs. The Padres got off to a quick start, with a run in the first on a passed ball. They then continued that momentum into the second, getting four hits to score five runs. Ben Sauerman, Carter Myer, Luke…

Dodgers Battle to Beat Red Sox

June 14, 2021

By Eric Xu This was a very close game between these two teams. The first inning started with an early Red Sox lead with Sean Boyd and Jack Silberhorn getting home by Sam Pandolfo. Sam Pandolfo was also able to get home, a total of three runs for the Red Sox. Dodgers were also able…

Diamondbacks Beat Cardinals 16 – 6

May 25, 2021

by Eric Xu The Cardinals suffered a heavy loss this Friday. In the first inning, the Diamondbacks started with a strong lead of five runs. The Cardinals started with an amazing hit by Eli Krogmeler that resulted in a double, but unfortunately, did not result in a run. On the Diamondbacks, Max Phillips was able to hit a triple. Cole…

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