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When Andy Benjamin first started playing in New Castle’s adult softball league more than three decades ago, his son Matthew would watch from the sidelines and cheer him on. As he got older, he would sit on the bench to keep score. Once he graduated from high school, Matthew (better know as Matty B) finally got to play alongside his old man.

“Most of us have the same story,” Andy Benjamin said. “Our sons said ‘keep playing until I can play with you.’”

It’s a cherished memory for Benjamin and one of the many reasons he’s played and managed in the recreational softball league since 1982. With the New Castle softball season in full swing, a remarkable 24 teams and close to 500 players are part of the program that is filtered into three leagues. It’s an impressive number of participants considering when Benjamin first started there was a little more than half that number of squads.

Benjamin, who played baseball in high school, described a league that has evolved and changed over the years. It’s a “user friendly” league, which makes it more enjoyable for those involved, Benjamin said. When he first started, anyone who worked at a business in town could play, even if they didn’t live in New Castle. That would result in an influx of “ringers” (superior players who would join the game under false pretenses.)

“In the beginning it was like the Wild West,” he said. “Everybody worked for somebody in the town. If there was a restaurant (that had a team) everybody was a part-time waiter there.”

Now, players need to live in the town or work for the town, Benjamin said, and that has resulted in more parity and fair competition in the league. He said two forms of proof are necessary to enter the league.

There are three divisions in the program depending on talent level and age. The A, B, or C league, with the A league the most competitive and the C league the least. Games typically last about an hour and 15 minutes.

New Castle recreation supervisor Doug Scott, who runs the softball program, said for the size of the town, the number of teams and players is above average. There are multiple teams that have been in the league for at least 20 years, he said and there are some players that are into their 60s that still play.

One advantage compared to other towns that New Castle can boast is it has lights at one of its softball fields, which can lead to more games per week. For those residents that commute to and from New York City on weekdays, it gives them the chance to still make their game that night. Instead of playing only one game a night, New Castle’s softball league can fit three games in, Scott noted.

Overall, it’s just a good group of guys engaged in friendly competition, Scott said.

“It’s been a community tradition,” Scott, who is in his second year running the softball games, said. “A camaraderie thing for a lot of guys. They get together, get outside, have a good time, go to the bar after. It’s just a good, fun way for them to spend time together.”

Aaron Podhurst, who ran the softball games for 17 years when he worked for New Castle, said considering only residents are allowed to play, to have close to 500 players is an impressive number. If there were more fields in town, Podhurst, who is now the Hastings-on-Hudson recreation department superintendent, thinks the program could’ve even expanded to more teams and players. There is generally a waitlist of players that want to join the league, Podhurst said.

Podhurst also mentioned having lights at one of the fields as a “tremendous advantage” that helps attract more players.

“It’s a great way for the adults to have some recreation,” he said. “They love to devote some time to something they actually enjoy. It’s just a great way to spend a night.”

While some towns and villages that have softball leagues include business and corporation teams and are simply looking for the most skilled players, New Castle prefers people within the community.

It’s led to special bonds between the men.

Benjamin said he doesn’t just consider his longtime teammates friends, but brothers. After almost every game on Tuesday nights, they all go to Quaker Hill Tavern to relive the ups and downs of the ballgame. They’ve gone to each other’s weddings, birthdays and their children’s bar mitzvahs. They even all went out to Arizona together once to play in a softball tournament hosted by Sports Illustrated.

Even players on different teams cultivate relationships with each other, Benjamin said.

“We do it for the fun, we do it for the competition, we do it for the camaraderie and when you play with guys for a long time, you develop a brotherhood,” Benjamin said. “There are 500 guys who just want to get out and go hit a ball and have some fun and share some good times.”