Pre-Season Training | Weekly on Sat at 9AM

Get ready to kick off the season with energy! Pre-season instructional training starts in January with weekly sessions alternating between defensive skills (throwing, fielding) and offensive skills in the batting cages. All sessions are located at New England Hitting and Pitching Academy located at 5 Wheeling Ave, Woburn MA.

Led by enthusiastic club and high school coaches, as well as current high school athletes, this training is all about building confidence, improving fundamentals, and having fun. It’s the perfect way for young athletes to grow their game and get excited for the season ahead!"

Spring Season City League

At 14U, Winchester teams compete in the City League against nearby communities including Arlington, Medford, Charlestown, Belmont, Watertown, Brighton, Waltham, and several other local towns. Games are currently played on Saturdays  (subject to change) and offer a perfect mix of challenge and fun. This division is a mix of 7th, 8th and 9th graders who are looking to continue their softball journey.

Winchester fields multiple teams made up of Winchester players selected by our coaches, with additional practices scheduled by each team’s coach. This league is a fantastic opportunity for players of all skill levels to grow their game, build confidence, and enjoy competitive softball in a supportive, upbeat environment.

Summer Season

Winchester Youth Softball turns up the excitement in the Middle Essex Summer Program! This league brings together teams from across Middlesex and Essex Counties for fast-paced games held Monday–Thursday at 6:15 PM. Summer ball offers a more competitive atmosphere than the spring season, giving players a chance to face stronger opponents, sharpen their skills, and experience a higher level of play—while still keeping the focus on fun, teamwork, and a genuine love of the game. Practice schedules are set by your  coaches, ensuring each team gets the training they need to shine all summer long.

Fall League 

Fall Ball is the perfect way to keep the softball fun going after summer! For our 10U and 12U and 14u athletes players, currently we are in the " Charles River Softball League" , where the focus shifts to learning, improving, and enjoying the game in a more relaxed, less competitive environment. Teams play a Sunday morning doubleheader—just enough action to kickstart the day—then you’re free to enjoy the rest of your weekend. It’s a great chance to stay active, build skills, and play with friends while soaking up those fall vibes!