About Winchester Youth Baseball & Softball (WYBS)

Winchester Youth Baseball & Softball Association (WYBS) provides baseball and softball activities for children of the ages of 6 to 18. To be eligible, children must live in the town of Winchester. For baseball, players must be age 6-15 as of April 30 of the playing year and they are assigned to leagues for their designated age groups. For softball, ages are roughly equivalent but assignment to leagues is based on school grade. Exceptions to these age and grade assignments are not made for playing ability or other factors.

Activities are available mainly during two seasons, the spring season and the summer season. The spring season, which is primarily instructional, is open to all children who are registered on time and consists of practices and games from late April to late June in leagues organized by age group and sometimes by playing ability. The youngest children are also grouped according to school attended whenever possible. The summer season is more limited as to age groups and to players who are quite serious about pursuing the sport. Summer baseball and softball are generally more competitive and more demanding on families during a period when they might be engaging in other activities. To assure that the quality of both seasons, anyone wishing to be eligible to play during the summer must also play in the spring.

Our organization is planned and executed by our Board of Directors. As a not-for-profit organization, we rely on volunteers to perform the many functions needed to give our kids a worthwhile experience. For some positions, such as coaches, we offer training to assure that our volunteers have the background and understanding of what it takes to do their job well.

Our program is affiliated with Babe Ruth League, an international organization that offers the opportunity for tournament play, a comprehensive insurance package and considerable flexibility in how we manage our spring and summer seasons. Babe Ruth covers both baseball and softball, with baseball being subdivided further based on playing age. The 12 and under division is known as the Cal Ripken Division. Descended from the previous Bambino Division, it was renamed for the 1999 season in honor of the future hall-of-fame infielder of the Baltimore Orioles.

WYBS.org is used to facilitate our ability to serve our community. If you join WYBS, you will receive periodic emails so you will be up to date with what and when things are happening. Members can also log in to find out what family members are registered to play, what teams they are on, game and practice schedules, and more.

WYBS Board of Directors

Chris Gannon

Executive Vice President
Matt Silberhorn

Rich Masterpol

Gina Richardson

Player Agent/Registrar
Janine Kutylo

Clint Myers

Advisor & Town Liason
Rich Michienzi

Equipment Manager
Matt Silberhorn

VP Baseball (13 & over)
Chris Porter, Steve McCabe

VP Baseball (10-12)
Chris Gannon

VP Baseball (6-9)
John Gillis

VP Softball
Jason Capodanno

VP Softball (10U)
Ryan Tate

VP Softball (12U)
Chris Lisy

Cal Ripken/Babe Ruth
Michael Creane

Player Development - Baseball

Player Development - Softball
Brian Gugliotta

Field/Schedule Coordinator

Nutile Field Leader – Baseball
Rich Masterpol

Nutile Field Advisor
John Tighe

Summer Coordinators

Andrew Statiris

Sportsmanship Coordinator
Steve McCabe

Jack Seitz
Marshall Daniels
Matt Capobianco

WYBS.org Website
Jack Seitz



"Winchester Little League is fantastic.  We're so proud to have been sponsors for over 20 years.  Thanks to all the volunteers that make the league so special."

2022 Board of Directors Meetings

Wednesday, January 18, 2023
7:30 PM, Winchester Town Hall

Monday, March 7, 2023
7:30 PM, Winchester Town Hall

Monday, October 15, 2023
7:30 PM, Winchester Town Hall

Monday, November 27, 2023
7:30 PM, Winchester Town Hall

Want to Become a WYBS Sponsor?

By participating as a sponsor of WYBS, you and your organization are given the opportunity to gain outstanding visibility to the Winchester Community through our new website, signage, uniforms and game reports in the Winchester Star.

More importantly, you have the opportunity to give back to your community by supporting a recognized, successful youth program.

Want to Help? Sign up to be a Volunteer!

What can be more rewarding than helping youngsters achieve their dreams?

As a not-for-profit, all-volunteer organization, we rely on the help of our community. Volunteering to help WYBS can truly be a labor of love. If you have skills, we will be delighted to put you to work. If you don't, we'll train you!  Interested?  Drop us a note.

WYBS Sponsors