A full-size professional pickleball court is about to take over one of the busiest patches of pavement in the country. Starting August 26, Times Square Plaza will host CityPicklepalooza, a five-day pop-up offering free open play, pro-am exhibition games, and beat-the-pro sessions right in the heart of Midtown.
The event is organized jointly by CityPickle and the Times Square Alliance, according to Time Out, which first reported details of the activation. Free open play runs throughout all five days, with sign-ups opening soon on CityPickle's website. The temporary court will be surrounded by activation spaces, including courtside cabanas built for spectators and sponsors alike.
Beyond the open play, organizers have packed the schedule with branded programming: Pickle Pong With Rhone, Cabot's Shoot Your Shot, On the Court With Prince, On the Court With K-Swiss, and K-Swiss programming paired with open play fueled by Zespri. There will also be interactive games, giveaways, prizes, a live DJ, and nonprofit community programming woven throughout the five days, per the same report.
Why Times Square, and Why Now
Times Square Plaza sees an average daily foot traffic of 350,000 visitors, and it sits adjacent to the busiest transit station in New York City, making it one of the highest-visibility spots imaginable for a pop-up sporting event. The plaza regularly hosts large public activations managed in part by the Times Square Alliance, according to CityPickle.
The timing is no accident. CityPicklepalooza's run coincides directly with Major League Pickleball's 2026 Finals, held August 28-30 at CityPickle's Wollman Rink facility in Central Park, which is hosting the MLP Finals for the second consecutive year, according to Forbes. The event also coincides with the start of the U.S. Open in Queens, whose Fan Week and qualifying matches begin August 23 ahead of main-draw play on August 30 — a stretch that brings hundreds of thousands of tennis enthusiasts to the New York area annually, per CityPickle.
A Company Built Around Court Scarcity
CityPickle isn't a stranger to Manhattan real estate. The company opened a permanent 37,000-square-foot flagship in February on the eighth floor of the Paramount Building at 1501 Broadway in Times Square, just steps from where the pop-up court will sit. That venue features seven indoor courts and a full restaurant and bar, offering more than 2,400 court hours per week, according to Resident Magazine.
The Paramount Building itself dates to 1927, built originally for Paramount Studios. Its rare column-free interior construction is what allowed designers to fit seven full-sized pickleball courts inside the commercial office tower this year, a detail that fits into a broader wave of office-to-recreation conversions across Midtown Manhattan, according to Time Out's earlier reporting on the venue.
CityPickle also holds a 20-year license with New York City to run 14 seasonal outdoor courts at Central Park's Wollman Rink during the months when the rink isn't hosting ice skating, according to Pickleball.com. Hoodline covered that seasonal transition back in April, when the rink dropped ice for pickleball ahead of the 2026 spring and summer season. The company also runs a summer residency at Hudson Yards, offering open play and private sessions from June 1 through August 30.
The Numbers Behind the Boom
CityPickle was co-founded in August 2021 by New Yorkers Mary Cannon and Erica Desai to address what the two saw as an acute shortage of dedicated pickleball courts in Manhattan, according to the New York Times. Before dedicated facilities existed, local players frequently set up temporary nets on cracked pavement just to get a game in.
That scarcity has given way to explosive growth. The Sports & Fitness Industry Association's 2026 report found that 24.3 million Americans played pickleball in 2025, a 22.8% single-year increase and a 171.8% three-year growth rate, according to Pickletile. Pickleball has been cited as the fastest-growing sport in the U.S. for five consecutive years running.
Spectators watching the pro-am exhibition games in Times Square may also notice a rules wrinkle. In January 2025, USA Pickleball introduced rally scoring as a provisional option for select doubles and tournament formats, awarding a point on every rally regardless of who served — a departure from traditional side-out scoring, which only grants points to the serving team.
