Cheshire Little League & Softball Celebrate a Memorable 72nd Season

The 2025 season marked the 72nd year of Cheshire Little League, filled with energy, growth, and community pride. From Opening Day festivities to championship games and new competitions, this year showcased the spirit of youth baseball and softball in Cheshire.

Opening Day at Cheshire High School

The season began in style as hundreds of players, families, and volunteers gathered at Cheshire High School for Opening Day. Team introductions, ceremonial first pitches, and community turnout set the tone for a great season ahead.

Greenwood Gauntlet Tournament

The CYB 2nd Annual Greenwood Gauntlet was another major success. Teams from both Majors and Minors joined in competitive play, sportsmanship, and fun—cementing this tournament as a growing Cheshire baseball tradition.

Baseball Season Highlights

• Majors: CYB Bombers took down Team Doyle for the Championship, 10-6
• Minors: Orange Devils defeated the Temu Mets 20–9 in an exciting championship game
• AAA: Team Milano topped Team DeHaan 17–10 to capture the title

Cheshire’s Little League All-Stars proudly represented the town this summer, competing with passion and effort both on and off the field.

Home Run Derby & Pitch, Hit & Run

• Home Run Derby: Congratulations to Joey "JMac" McKenzie for taking the crown!
• 1st Annual Pitch, Hit & Run: A great turnout and a new tradition for years to come.

Honoring Tradition

Cheshire Little League participated in the annual Memorial Day Parade, honoring those who served and connecting our baseball and softball families with the wider community.

Softball Highlights

The CT Charge travel teams had an incredible season with tournaments, games, and team bonding. Check out some of their most memorable moments below:

A Look Back in Time

Want to see how far we’ve come? Visit our CYB Archives page for a look back at Cheshire Youth Baseball as it approached its 50th year—a mix of photos, graphics, and snapshots from the early 2000s that capture the spirit of the league and its players. From scanned photographs to Paint-style artwork, this page preserves a piece of CYB history. Enjoy the trip down memory lane!

Looking Ahead

As we close the book on our 72nd season, we extend heartfelt thanks to our players, coaches, volunteers, families, and sponsors for another incredible year of baseball and softball. Planning is already underway for 2026, and with the enthusiasm and commitment of our Cheshire community, the future looks brighter than ever.