“People start playing squash to get fit,” says Terry Pritchard, one of the most enthusiastic players at Headwaters Racquet Club. “But soon you are getting fit to play better squash.”

Either way, the game is a heck of a good way to have fun while elevating your heart rate, putting your lungs to the test, and giving your grey matter a workout. “You play your butt off in 45 minutes on a squash court,” says Jamie Hickox – and he should know. Born in Oakville but now living in Caledon Village, Jamie was a top-15 player on the world circuit from 1982 to 1997 and is currently Squash Canada’s performance director. Squash is like “chess on legs,” he says. “You have to think three or four shots ahead.”

Unlike tennis, squash is always played indoors in a cube-like room, 21 feet wide and 32 feet long for singles play. The racquet and hollow ball are smaller than those used for tennis, and there is no net. Instead, players take turns hitting the ball against any of the four walls, though it must hit the front wall at least once during any shot. A rally ends when a player fails to return a shot before the ball bounces more than once on the wooden floor, giving a point to the opponent. Games are played to 11 points, with a match being the best of five games.

Terry was a rank beginner when he picked up squash at the Headwaters club about five years ago. He remembers how nervous he was at his first tournament. “I thought it would be very competitive,” he recalls. “In fact, what we found was the opposite. It was sort of a family atmosphere.”

Terry’s experience matches that of most squash players, who comment on how social the game is. Leah Desbarres, the squash pro at Headwaters, says, “There’s always lots of socializing among squash players after a match.”

Leah, who has played the game since her early teens and ranked for many years among the top 10 players in Ontario, gave me a few pointers one day in the fall. I thought I was doing pretty well – until I asked her to play as if she were in a tournament. So she dropped shot after shot into the back corner, giving inexperienced, tennis-playing me no room to swing at the ball.

Taking pity, she told me to try a “boast,” a strategy that involves banking the ball off a side wall straight to the front wall. In this way, the game is a little like billiards. Leah’s suggestion helped, but the manoeuvre left me vulnerable to her next shot, which she dropped neatly into the opposite front corner so I had to dash madly to return it – whereupon Leah stroked the ball leisurely, hitting a line drive that was out of my reach.

“I’m not a power player,” she explains, “but I can place the ball pretty well.” Her accuracy frustrates a lot of big, strong heavy hitters, she says. No kidding.

“Hitting the ball hard is an advantage, but it isn’t everything,” says Jamie. His favoured shot is a “working boast,” essentially the shot Leah instructed me to use to get the ball out of a back corner. His love of squash developed from his enjoyment of hitting things against a wall as a young boy. After that, he says, “Imagine how much fun it was to have four walls to play against.”

This kind of childhood obsession, the repetitive sound of which can drive parents crazy, was critical to the development of the game, which originated in the Fleet Prison in London, England – a place where you’d expect people to spend a lot of downtime amid concrete walls. To pass the time, the debtors who made up most of the notorious prison’s population hit balls against the walls of the recreation yard. By the early 1800s this pastime had evolved into a game called rackets, a precursor of squash.

Then, “by some strange route,” wrote Ted Wallbutton on the website of the World Squash Federation, rackets made its way to Harrow, arguably the most prestigious school in England. Though it’s hard to imagine Harrow’s privileged students running out of balls, they must have, for squash emerged when the boys realized how challenging it was to play with a punctured rackets ball that “squashed” when it hit the wall.

Although squash doesn’t enjoy the popularity of tennis, squash aficionados hope this will change if the game is included in the Olympics. The campaign to make this happen recently suffered a setback when the Tokyo 2020 organizing committee rejected the World Squash Federation’s proposal, but officials aren’t giving up on their dream of making the game an Olympic sport.

Here in Canada, the game is played by about 200,000 people – and for a while the country boasted an acknowledged superpower on the world scene. Colourful and outspoken, Jonathan Power was the world’s number one player when he retired in 2006. Caledon has a few players to brag about too. From Palgrave, the two older Riedelsheimer brothers, Sebastian and Christian, both attended American universities on squash scholarships, and their younger brother Alexander will learn this winter whether he, too, is heading south of the border.

Asked what he considers his main advantage, Alexander says, “I’m pretty smart on the court and I’ve got pretty good hands.” These capabilities will no doubt help the 17-year-old realize his other dream: to become a doctor.

Meanwhile, I have to towel off after my short lesson with Leah. My damp shirt is all the proof I need that squash is a great workout, and figuring out all the angles is way more fun than sitting on a stationary bike. Leah admits she wanted us to play so I’d be reminded of squash’s “awesomeness.” Her ploy worked.