Not your
parents’
racquet club:
The entrepreneurs building a pickleball empire
Pickleball’s boom may have started three years ago, but Fairgrounds founders Drummond Munro and Matt Rubinoff are showing there’s still plenty of game left to play.
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If pickleball is the more laid-back version of tennis, Fairgrounds is the more laid-back version of the traditional racquet club.
Founded by two consumer retail veterans as a pop-up project at Yonge and Eglinton in the summer of 2023, the free-to-join pickleball and padel club has exploded in popularity, boasting over 54,000 members across four locations in the GTA, with many more on the way.
“I started looking at the space holistically, and realized that there was a pretty massive gap,” explains Fairgrounds co-founder Drummond Munro. “On one side you have public infrastructure - putting your racquet on a fence at Trinity Bellwoods Park to signal you’re next up on these courts with grass growing through the cracks - or private clubs that are quite expensive, with dress codes and etiquette rules.”
The long-time racquet sports enthusiast and consumer retail professional first discovered pickleball while visiting his family’s home in South Carolina in 2018. By the time he temporarily relocated there during the pandemic, Munro says it had become nearly impossible to book a court due to overwhelming demand.
“It entered the cultural conversation in a way I hadn't seen any other sport do,” he says. “Then after COVID everyone was prioritizing being outside, being connected, and pickleball has that in its DNA.”
In 2023 Munro partnered with STACKT Market founder Matt Rubinoff, and after the success of its initial pop-up, opened the first permanent Fairgrounds location in Cloverdale Mall in February of 2024. Three more outdoor venues followed soon after.
As they expanded their footprint Munro says they also expanded their offering, adding the squash-like Mexican racquet sport padel. “We’ll be opening a flagship location in Leaside - which will be our biggest location to date, with 12 pickleball courts and four padel courts - in the old Mercedes-Benz dealership at Eglinton and Laird on May 15.”
“Pickleball isn't just a trend - it's evolving. People want spaces to connect, hang out, and play. That's what Fairgrounds is all about.”
— Drummond Munro
Now the founders are preparing to expand nationally, with plans to open Fairgrounds locations in Vancouver, several yet-to-be-revealed cities in Alberta, Kingston and beyond.
Building a pickleball empire hasn’t been all fun and games. In fact, it’s been a “a constant cycle of learning, iterating, and adapting.” In the 13 months since they opened their first permanent facility, Drummond says they’ve tested just about every operating model possible, from indoor, outdoor, pop-up and permanent, with each site having its own particular set of variables to manage.
“The biggest challenge has been building while operating - learning in real-time, often without a playbook. But the upside? We now have a full year of real-world data to help us make smarter decisions and continue optimizing,” he says. “We’ve moved quickly, made mistakes, adjusted, and ultimately emerged more confident in what works - and just as importantly, what doesn’t.”
Yet despite these hurdles, Fairgrounds has managed to stay true to its easygoing roots. For example, membership is free and playing time is only $10 per person per hour, with some brand-sponsored events available at no cost. The venue also hosts DJ events on Fridays, children’s events on weekends and themed events like pickleball speed dating.
“We're trying to offer the private club amenities, but for a larger population,” Munro explains, adding that the new flagship location will feature saunas and cold rinse showers. “Even from a design approach Fairgrounds is intentionally very colourful and pulls a lot of inspiration from pre-existing public spaces, like using the galvanized chain link that you’d see in the park as our dividers.”
Munro says unlike a traditional racquet club, there is no dress code or etiquette rules, ensuring the club remains open and approachable to anyone with an interest in racquet sports.
“That could be 12-year-olds joining our kids programming on the weekend, the 87-year-olds coming from retirement homes to play in Cloverdale, and everything in between,” he says. “This sport just resonates with everyone. It's about bringing joy and happiness and getting active and connecting with the community, and I think that checks a lot of boxes for people right now.”