Tim Dempsey is the oldest player in the Montgomery Over 50 Softball League, but in the league, he has found a Fountain of Youth.

“This is great,” said Dempsey, 71. “Those of us who played Little League ball in Montgomery 60 years ago, or more this really takes us back.”

The league, which was founded by Ron Lewis, meets on Saturday afternoons at the Berea Field, starting in April and running until the end of August, and has been in existence since 2012.

“I was playing across the river in the Poughkeepsie area, and that was a 60-and-over men’s league,” Lewis said. “So, that’s where I got the idea to bring this over here, but I got the age limit down to 50 because I thought we would have a better shot of getting more players in that age group.”

This was before the spring of 2012. Phone calls were made, and Lewis took down names of people who wanted to play, and the names were put in a hat for a league draft. Lewis didn’t want a stacked team that would dominate the league.

“That’s the reason I did it that way,” Lewis said.
The first season – 2012 – the league had five teams, three of which were built from the league draft. Two other teams came in already established.

“I knew who they were from playing against them in the (modified-pitch over-30 league I previously ran),” Lewis said. “So, I let them come in.”

At its height, the league had 6 teams, but this season it had five after Lewis’ “Blue” team stopped playing after last season. Lewis also stepped down as commissioner, and was replaced by George Hammer, who also serves as home-plate umpire during games.

There also are some rules to accommodate the age of the players. If a batter needs it, he can have a special pinch runner, which starts from a line near the backstop on the way to first base. There are also pinch runners if a player can run to first base, but not all the way around.

There is also a run-rule designed to keep the games close and running on schedule. In the first six innings, the inning turns over after the offensive team scores five runs. In the seventh inning, both teams need to achieve three outs.

Therefore, no game is out of reach.

There also is a commitment line between third base and home. Once a base runner passes that line, they can’t return to third base. There also is a square base near the backstop for runners to score to prevent collisions at home plate.

“All the catcher has to do is have his foot on the board,” Lewis said. “If the ball gets there before the guy reaches the other base, it’s an out.”

Then there’s the board, a piece of rectangular plywood on the home plate area, that eliminates any argument over balls and strikes. If the pitched ball hits any part of the board on the fly, it’s a strike. The slow pitch has to have an arc from 6 to 12 feet. If it doesn’t meet that criterion, it’s called a ball.

The league started with five teams, Blue, Red, Yellow, Black and Green. Eventually a Camouflage team joined to bump up the league’s numbers to six. The Blue team folded after last season, knocking the number down to five. The teams did pick names; the Blue team was the Marauders, the Red team was the Raiders, Yellow was the Yellow Jackets, Green are the Dragons and Black had the most entertaining name of all, BOOGS (Bunch of Old Guys).
Camouflage are the Flames.

The league has been competitive with all six teams having won the championship at least once. BOOGS have won the championship twice (2015, 2016), as has Green (2018, 2019) and Camouflage has had three titles (2017, 2020, 2021).

Three games are played each day, starting at 12:30, but with five teams that means every week one team plays a doubleheader.

It does get competitive, and there’s plenty of banter between the players on both teams, most of it good-natured.

“It’s a fun league,” Dempsey said. “To go and have fun here is really what it’s all about. The teamwork is superb. It’s competitive because we’re all on teams. We do keep score, but for me, it just takes me back. At the ripe old age of 71, I’m happy to still be playing a competitive sport. And that’s all thanks to Ronnie Lewis. He’s our founder.”