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 for the Spring 2021 Baseball season is now open for all levels.
The deadline for registration is March 15th, so don't wait!

Baseball Registration

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.


Registration for the Spring 2021 Softball season is now open for all levels.
The deadline for registration is March 15th, so don't wait!

Softball Registration


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!


Registration for Winter Clinics is now open for 8 and 9 year-old Baseball.
Sessions will be held at Route 2 Athletics in Arlington. Spots are limited!

9 year-old players:
Sundays 12:00PM - 1:30PM
February 7 - March 28

8 year-old players:
Mondays 3:30PM - 5:00PM
February 8 - March 29

Game Recaps

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

Marlins Pounce on Cardinals to Win 17-4

September 21, 2020

By Jack Siciliano The Marlins scored runs early and often on Friday, September 18th against the Cardinals. They scored three in the first inning with RBI hits from Luke Molloy and Freddy Meyer, who would both come around to score as well. They added five more in the second with a few walks and RBI…

White Sox Narrowly Edge Red Sox 11-10

September 18, 2020

By Jack Siciliano The White Sox and Red Sox played a really close one on Tuesday, September 15th. Both teams went down in order in the first inning, but the scoring heated up in the second. Stephen McCabe and Tommy Kowalczuk started the inning with hits and were brought around on an RBI single by…

Red Sox Outplay Marlins 8-6

September 17, 2020

By Jason Feng On Monday, the Red Sox hung on in a tight game to beat the Marlins 8-6. To start off the game Steve McCabe hit a double to score Jack Allen. In the bottom of the first, the Red Sox held the Marlins scoreless thanks to great catches from Ryan Kutylo and Quinn…

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