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WINDSOR LITTLE LEAGUE - Opening Day is April 20th!!!


Updated 11/16/2023

Any player League age 8 and older (*potentially 7 and older for Softball) will be required to participate in evaluations to help us determine divisions and teams.  

Please note the evaluations will be held in the beginning of April with dates and times that will be filled in on the table below when they are ready.

DateTimeSoftball/BaseballAge Range


Evaluation Location:

  • LP Wilson 

Protocols for players:

  • Players must bring the following equipment:
    • Helmet
    • Glove
    • Bat
    • Defensive Facemasks (Softball only)
    • Sneakers (rather than cleats for use indoors)
    • Water Bottle 


Parents can play many roles in sport: current or former athlete, coach, fan, motivator, role model or critic. A few studies have shown that family members may influence an athlete’s involvement and achievement in sport more than coaches. Parents also are the first and most critical agents at socializing sports.



What equipment does the League Provide?

  • Bats (suitable sizes by age and division)**
  • A few batting helmets per team**
  • Catcher's gear, glove, mask with throat guard
  • Baseballs and/or softballs for practices and games
  • Team Uniform Jersey
  • Team Hat
  • Team Socks (if need)

What equipment is parents/guardians responsibility?

  • Baseball/Softball Glove
  • Defensive Facemasks (Softball only)
  • Batting gloves (optional)
  • Rubber-soled cleats (optional for Tee Ball)
  • Backpack or equipment bag (optional)

**2022 COVID Protocols require players provide their own. If unable to, please contact [email protected] for equipment lease details



When does the 2024 season start?

Windsor Little League kicks off the season in April. Opening Day is being scheduled for around late April which we celebrate with a parade and ceremony. Practices may be scheduled prior to then, as well as a few games for players at the older levels. 

How many games are played each week?

It depends on the level of the player. Players in t-ball, A, and AA will usually play two games per week. Player in AAA-Juniors can play up to 3 times per week.

How many practices are held each week?

Practices may be once or twice a week depending on the level your player is in.

What days will practices and games be held?

The official schedule will not be released until early April. This is because the teams at higher levels verse teams from other towns, and it is a big, collaborative effort to schedule between so many towns and teams. We ask for patience while we determine the schedule, but will update you as soon as we can.

In which division will my player be placed?

If your child is aged (league age) 5 and has never played Little League before, the first stop is t-ball.

After one year of t-ball, your child would be eligible to start in minors, typically at the A level. Minors starts at A, then goes up to AA, then AAA. Typically, players in the A division are ages 6-8. AA hosts players between 7-9. AAA welcomes kids 8-11. Majors is for players 9-12. A formal evaluation is held each year for players 8+ to ensure they are placed in the appropriate division. Coach’s feedback from prior years may also be applied. 

If I want to request my child be on the same team as a friend, or get a specific coach, how do I ask?

You may send all requests to [email protected]. We will do our best honor requests, but we cannot make any promises. Our league consists of roughly 250 players, so please understand that it would be nearly impossible to meet every request.

Why does my child need to participate in evaluations?

Most organized sports require an evaluation, even if the player is a returning player. It’s very important to the safety of the whole team to know where each player evaluates.  Baseball and Softball will evaluate players ages 8+ .

My child has played Majors for two years. Will he/she still need to evaluate?

Yes. Players, even returning ones will be required to evaluate.

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