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Cheshire Youth Baseball and Softball

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.

Update 3/1:
Little League divisions T-Ball through Majors are now in LATE SIGN-UPS ($15 processing fee). Registrants will be accepted where team size permits. Join the waitlist to show your interest in participating in the Spring 2026 season.
Intermediate and Junior divisions remain open at the standard fee until Dodd Middle School baseball team selection is complete.


New in 2026:
  1. 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.
  2. 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!
  3. 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 includes all offensive and defensive rules of the game on the big field!
All games in the senior divisions have two umpires on the field. Cheshire will participate with other towns in District 4. The CT Little League District map is available HERE.

Preliminary Schedule Details:
  • Player evaluations for both Minors and Majors will be held March 1st 3:30p-6:30p @ Highland Gym. Minors and Majors players may attend at any time.
  • 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.

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 512. Further details provided in program registration.

AAA - Hybrid (Coach & Player) Pitch Baseball

Registration closes on 04/04/2026 at 11:59 PM
Season Dates: 03/15/2026 to 06/21/2026
Show Details
$235.00

Cheshire Challengers Registration

2026 Cheshire Challengers

Cheshire Challengers Little League program is designed for, and is open to, special needs athletes only. The league strives to maintain a positive atmosphere at all times while offering an enjoyable learning experience for our athletes, volunteers, and supporters.   Players participate in both home and away games as well as skills clinics and other Little League activities.

The Little League Challenger Division is Little League’s adaptive baseball program for individuals with physical and intellectual challenges and accommodates players ages 4 to 18; or up to age 22 if still enrolled in school.

Challenger - Little League Challenger Division

Registration closes on 04/05/2026 at 12:00 AM
Season Dates: 03/01/2025 to 06/01/2026
Show Details
$0.00

Reds Travel Baseball

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There are no programs or divisions available at the moment. Please contact your club administrator with any questions.

Comets Travel Baseball

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There are no programs or divisions available at the moment. Please contact your club administrator with any questions.

Local Sponsors

Cheshire Youth Little League

550 Wiese Rd 
Cheshire, Connecticut 06410

Phone: 203-699-6622

Email: [email protected]

LITTLE LEAGUE® International

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