Baseball Programs

Cheshire Little League Baseball Registration

2026 Spring Baseball

CYB Spring 2026 Little League Baseball - Recreational Leagues

Review Cheshire Little League's division structure HERE before proceeding to register to make sure your player is in the right place! The Cheshire Little League Spring season runs indoors in March and moves outdoors in April until mid-June.

New in 2026:

The town of Cheshire now charges field-use fees for both in-town and out-of-town residence. The in-town resident fee is $10/player. This fee has been incorporated into the league registration fee. Out-of-town players will see an additional $15/player fee at checkout.
We are excited to announce our increased partnership with the premier baseball & softball facility in town D-Bat Cheshire. With our limited field space, growing player numbers, and need for strong instructional development we now include in registration for all CYB players (AA and up) a 4-week pre-season clinic and indoor practices every-other week throughout the regular season. All D-Bat events are run by their professional coaching staff with support by CYB Coach volunteers. The program will develop baseball skills for players of all levels and keep us all moving no matter the weather!
Two senior division levels are now available for registration:

Intermediate (13U ): Is 50/70 format, playing on Mac4, and is designed to introduce baseball rules (ie. balks) and strategies (ie. leading, pick-offs) not permitted in Little League Majors level.
Juniors (14U): Is 60/90 format, played at Bartlem Park, and introduces all offensive and defensive rules of the game.

All games in the senior divisions have two umpires on the field. Cheshire will participate with the other towns in District 4. The CT Little League District map is available HERE.

Preliminary Schedule Details:

Players Evaluations (Minors & Majors) will be on Sunday Feb-1st and Saturday Feb-7th. Players will be assigned a time to attend after registration closes.
Pre-season clinics @ D-Bat will begin March 15th and run once a week for a month.
The 3rd Annual Greenwood's Gauntlet Tournament for Minors & Majors players will take place April 13th through April 19th.
Regular season games are expected to start on April 25th. Once games begin, there will typically be 1 weeknight game, 1 Saturday game, and 1 weeknight practice.
Games and practices are 2 hours each for all divisions except tee-ball which is only 1 hour.

Register early to guarantee your spot! To preserve quality playing time and balanced team size, Wait-Lists will be activated towards the end of the registration period. The league continuously monitors division enrollments and will make every effort to include all interested players.

The season schedule will be posted after registration closes and teams are drafted. A communication on evaluations for Minors and Majors divisions will be emailed and posted on www.cybcys.org following registration closure.

The final schedule is based on the number of participants and the number of teams created for each division. If a division within Cheshire Little League does not have sufficient teams (at least four) to support in-town league play, those teams will participate in District 4 LL season games. This will require local travel to surrounding towns. The CT Little League District map is available HERE.

Credit card payment is due at registration. Checks may be mailed to the CYB's PO Box. Further details provided in program registration.