Mary Cannon and Erica Desai, friends who founded CityPickle in 2021, have turned their idea into a racket-sport powerhouse that recently opened what’s billed as New York’s largest pickleball club in the tourist-and-entertainment hub of Times Square.
The 37,000‑square‑foot flagship, located on the eighth floor of the historic Paramount Building at 1501 Broadway, marks CityPickle’s first year‑round location in Manhattan and comes nearly 60 years after the famed Paramount Theatre — which hosted performers including Frank Sinatra — closed at the site in 1966. The Times Square venue also serves as CityPickle’s corporate headquarters and features a full‑service bar and restaurant.
The opening follows CityPickle’s debut of New York’s first indoor pickleball club in Long Island City in 2023, across the East River. The company is also set to expand this spring with a 60,000‑square‑foot Brooklyn Bridge outpost in the Dumbo neighborhood, while continuing to operate seasonal locations, including one at Related Cos.’ Hudson Yards, where its first pop‑up opened in 2022.
The startup recently signed a 20‑year agreement to operate CityPickle at Wollman Rink, the former pop-up location, on a nearly year-round basis during non-ice skating season, also in partnership with Related, part of the group that operates the famed Central Park attraction. Outside New York, CityPickle operates a seasonal location at Philadelphia’s Dilworth Park, adjacent to City Hall. The company also plans to expand farther south with plans to open Boca Paddle by CityPickle, a 100,000‑square‑foot indoor‑outdoor pickleball and padel complex, in Florida later this year.
As far as what could come down the road, Cannon said cities where CityPickle would be interested in expanding include Boston and San Francisco domestically and Toronto and London internationally.
CoStar News spoke with CityPickle’s co‑founders, Cannon and Desai, about the company’s origin story, the rationale behind opening its first office‑building location in Times Square and what comes next. The following interview has been edited for length and clarity.
As longtime tennis players, why did you pivot to a pickleball club?
Desai: Mary and I are longtime friends. We played lots of tennis together over the years. During COVID, we each separately took a trip outside of New York and learned how to play pickleball, and thought it was so much fun that when we came back to New York, we wanted to continue to play. We realized at that time that there was nowhere to play pickleball — not one single dedicated pickleball court in all of New York City. The world was coming out of COVID at that time. We thought that New York City needed ways to come together in real time and space and have shared experiences and be together, and pickleball is just fun. … We also love to eat and drink, so we thought combining the food and beverage with pickleball would make it even more special and really emphasize that social nature.
Cannon: Tennis is incredibly expensive [here]. It's harder to find people who are your exact level in tennis. Pickleball is a little bit more forgiving — less expensive — much more accessible, particularly in New York City. And it’s not as physically demanding. So you can do it many times a week.
What led you to open your first Times Square location inside a historic office building?
Cannon: Times Square is the crossroads of the world, right? If you live in New York City, on a subway, you can get to Times Square in no time. Erica and I have looked at over 80 locations with our real estate brokers, and this location, the moment we walked in, we knew this was perfect. For a pickleball facility, you need high ceilings; this space has no columns. This was a homerun. It is on the eighth floor of an office building. We are a destination. It’s [us paying] office rent, not ground-floor retail rent. We wouldn't have 37,000 square feet in a traditional retail space, because that probably would not be cost effective for us. In addition to people paying to rent courts or to take lessons or clinics, we also do a lot of private events, [which] really are an important part of our revenue. Our Long Island City location is profitable.”
Desai: It's like a little oasis in Times Square. You don't necessarily expect it to be on the eighth floor of an office building. That adds to what makes it so special, because you come off the elevator and here it is. It's a little unexpected. That's like a very nice surprise and delight moment.
You said you met 17 years ago when your kids were 2. What backgrounds helped you crack the code on launching a profitable venture?
Cannon: Our professional backgrounds have been perfectly complementary to do what we're doing. I started my career [at Goldman Sachs] in finance and in investing, particularly in real estate. I then worked for Charlesbank Capital Partners, a private equity firm. We've been successful because we are very creative thinkers, and we are good with real estate, and we're hard workers. This is a really great culmination of our professional skills, and it really matches sort of the passion of how we like to live — we love any racket sports. We still play tennis.”
Desai: I worked in public health. Wellness and operations was a big part of what I did. When my kids were young, I did lots of nonprofit work and things at their schools and kept my skills going as much as I could.”
So how often do you play pickleball these days?
Cannon: “Not enough. We are building a business, so we work a lot. We love playing with each other, but we also love playing with our families. I have three children, and they love to play pickleball. We play often as a family. I was playing with my husband and my 16-year-old son on Sunday. It’s so much fun.” (Cannon, who lives in Manhattan’s Union Square neighborhood, and Desai, who lives in nearby Flatiron, said the Times Square location is where they often play with their families.)
How concerned are you about increased pickleball competition — and what separates CityPickle?
Cannon: There's still a supply-and-demand, massive imbalance. [On] weekends and after work, I wish we had 20 more courts. We're cheering on the other clubs. The demand is so high. We can all be winners here. We make it a real third place, where you feel comfortable [and] have everything you need under this roof.
Desai: Different clubs take different approaches. We want to build that strong community, and we want to make it easy for everybody to do that. We have a lot of amenities to help people fit pickleball into their day. We have the phone booths available to people if they need to jump on a call afterwards. We also have three showers. We have a restaurant and bar. We want people to have reasons to stay. We have professional cushioned courts. Anybody who makes a reservation can come and play here [without a membership]. That really distinguishes us.”
What’s next for CityPickle in New York and beyond? Are more office buildings part of the game plan?
Cannon: We've proven this model can work very well in an office building. We have spoken to a lot of large office real estate operators. They understand that this is an amazing amenity, especially as the trend is bringing your employees back into the office and making people excited for that. Everybody wants it, but do they have the real estate that works? The high ceilings, column-less space, it's not that easy to find in New York City. There are barriers to entry. So while we can't churn out clubs in dense urban areas, it protects us as a barrier to entry from excessive competition.
2026 for us is a massive expansion year. There's other places in the city that would make sense. Tribeca would be a great location [as] are areas on the Upper East Side where there's a lot of population density. We are pursuing other locations in other cities where it's not easy to play pickleball and also have a thriving number of companies co-located that can host events with us. If we were to open a couple every year, that's probably realistic.”