Former players of the famed Winchester Fastpitch Softball League converged at the Golden Corral on Bypass Road to share memories, laughter, and camaraderie. Though the league itself has been dormant for years, its spirit remains vibrant among its alumni.
For decades, the Winchester league held a unique place in Kentucky fastpitch history. Operating primarily out of Massie Park, it welcomed teams from Louisville, Grant County, Georgetown, and beyond. It even expanded its reach by hosting state tournaments—drawing participants across the Commonwealth
“It’s just been…a great time,” reflected former pitcher Gary Willoughby, who helped orchestrate the event. “We’re having this so we can everybody see each other and talk about all the old games and reminisce”. For many, it was more than competition—it was family.
A League with Far‑Reaching Roots
The league’s reach extended far beyond Winchester. Air Force veteran Mike Casey joined the Lexington team simply because Winchester was the only place to play fastpitch after his service, and he soon found camaraderie on and off the field. Danny Glass, who played for both Owen County and Georgetown, recalled his four appearances in the World Series—an experience shared with his family that remains close to his heart
Lexington native Curtis Carter pointed to the league’s popularity, with as many as 2,000 fans flooding tournaments—sometimes arriving on Greyhound buses—making events feel like a major spectacle. Fellow competitor Oney VanLandingham also emphasized the competitive nature of Winchester teams: “It was a real competitive league. … at least one or two of the Winchester teams would always be in the same tournament”
More Than a Game—Lasting Friendships
Yet what truly stood out at the reunion was the enduring human bonds. “We just had a ball, and we miss it so much,” said Willoughby, adding with hope, “I would love to see it come back”. That sense of longing and nostalgia echoed throughout the dining room.
This gathering wasn’t the first. Similar reunions at the same venue took place in recent years—May 2023, May 2024—and each saw dozens of former teammates. In 2024, veteran pitcher Bob Spencer, then-66, was still celebrated for pitching 20 no-hitters and four perfect games over a 35-year playing span
But this May 29, 2025, event brought fresh perspectives. It was less about individual feats and more about communal history, uniting generations of players—from early pioneers to those who joined as teenagers.
Highlights from the Night
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Massive turnout: Alumni traveled from Louisville, Grant County, and more, along with local Winchester former players.
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Personal stories: Players reminisced about standout tournaments, rivalries, and the weekend trips brought together by state-level play.
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Shared legacy: The league was remembered as “big time,” with packed stadiums and enthusiastic coaches and
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Future hopes: Discussions floated about possibly reviving the league, though no formal plans were announced.
Reflections on the Game’s Impact
Many described the league as transformative. It offered structure, competition, and pure enjoyment. It also provided community—fields became gathering spots, and weekends became traditions. Even military personnel and far‑flung opponents found a shared home in Winchester.
Despite the league’s closure, its alumni remain connected—through annual meals, golf tournaments, and occasional softball pick‑up games. Gary Willoughby’s sentiment captured the mood for many: “We miss it so much—and would love to see it come back” .
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