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Paddles in the Plaza: How CityPickle Palooza Took Over Times Square

Written by CityPickle | September 2, 2026

What happens when you take our favorite sport, put it in one of the most iconic locations in the world, and invite some of the biggest names in pickleball and cool brands to join the party?

You get CityPickle Palooza.

From August 26–30, CityPickle took over Times Square for five unforgettable days of pickleball, brands, athletes, prizes, samples and seriously high energy moments. It was a celebration that proved just how powerful New York City brand activations can be when an ambitious idea meets an even more ambitious location.

But before the first players hit the court, there was a lot of work to do.

Overnight Hustle

The CityPickle Palooza experience officially kicked off at 9AM on August 26. However, the court wasn't there the night before.

The team had just one night to transform the space into a fully functioning pickleball destination in the middle of Times Square. While NYC slept, our amazing crew worked through the night to install the court.

By 9AM, the transformation was complete, and CityPickle Palooza was officially underway.

Day 1: Pickleball for All

We couldn't think of a better way to kick off Palooza than by making sure the sport was accessible to everyone.

We welcomed nonprofit Challenged Athletes, bringing pickleball to athletes who may not always have the opportunity to participate in traditional sports. The day was a reminder that one of the best things about pickleball is its ability to bring people together, regardless of experience or ability.

From there, the energy continued with Rhone's "Pickle-Pong" activation. Pedestrians were invited to put their skills to the test for a chance to win prizes, turning a walk through Times Square into an unexpected moment of competition and fun.

It was experiential marketing in its best form: don't just tell people about a brand. Let them experience it in an interactive way.

Day 2: The Pros Take Over

If Day 1 introduced New York to CityPickle Palooza, Day 2 showed everyone what pickleball at the highest level looks like.

Major League Pickleball brought the teams competing in the MLP Finals to our court, creating an electric atmosphere as some of the best players in the sport took over Times Square.

This made our court not just a place to play. It was the place to be.

And the excitement didn't stop at the court. Major League Pickleball also brought a massive screen to Times Square, streaming the MLP Finals throughout the weekend. Fans could experience the biggest moments of professional pickleball while standing right in the middle of the action.

However, the most epic part of the week took place with help from our partners at One Times Square: the iconic NYE ball was transformed into a giant pickleball. The CityPickle team and MLP teams got the chance to head up and see it up-close. Obviously, there couldn’t be enough pictures!

Prince was also on-site throughout the day, bringing its contagious, positive energy to the activation. From engaging with fans to customizing pickleballs, Prince proved that a little rain wasn't going to slow down CityPickle Palooza.

Day 3: Women, Wellness and Some Cheese

At 11 AM, the National Women's Pickleball Foundation hit the court, bringing an incredible group of visionary women together and showcasing the growing community around the sport.

Cabot activated throughout the day, handing out smoothie and cheese samples to hungry Times Square passersby. But they didn't stop at sampling. Guests also had the opportunity to get on the court during an hour of Cabot court time, where they could play, compete and try to win Cabot swag.

It was another great example of how immersive experiences can turn a brand interaction into something people actually participate in and remember.

Day 4: The Big One

Zespri handed out its delicious, famous golden kiwis, while K-Swiss brought court culture to Times Square. K-Swiss hosted court time featuring celebrity coach Matt Manasse for a "Beat the Pros" session, giving players the chance to test their skills against a professional.

K-Swiss also brought a truck loaded with gear that parked alongside the activation for the day, adding another highly visible brand moment to the already electric Times Square experience. It was a great example of how mobile tours and mobile brand experiences can complement a larger pop-up activation, creating multiple opportunities for consumers to discover and interact with a brand.

Cabot was back too, continuing to serve up yummy samples and bring its court time game to the Palooza crowd.

Between Cabot's cheese and smoothies and Zespri's golden kiwis, if you walked past CityPickle Palooza that day, you wouldn't leave hungry!

Day 5: One Last Rally

The final day brought back three of our incredible partners: Zespri, K-Swiss and Prince.

It was the perfect way to close out five days of pickleball and brand experiences in the heart of Times Square. Players returned to the court, brands continued engaging with pedestrians and the energy that had defined the week carried all the way through the final day.

More Than Pickleball

CityPickle Palooza was never just about putting a pickleball court in Times Square. It was about creating a destination and celebrating community.

A place where professional athletes could play in front of fans. A welcoming environment where someone new to pickleball could pick up a paddle for the first time. A home for innovative brands to create memorable interactions instead of digital advertisements. A moment when a giant New Year's Eve ball could become a giant pickleball.

That is the power of experiential marketing.

The best New York City brand activations don't just occupy a space. They become part of the city around them, giving people a reason to stop. They create moments worth photographing. They invite participation. And, most importantly, they leave people with a story to tell.

For five days, CityPickle Palooza turned Times Square into a pickleball playground and gave our partners a platform to create their own stories within it. Most iconic five days ever.

Thank you to our visionary partner, Times Square Alliance, who understands the power of an iconic location combined with creativity.