top of page

Imagine Skateboarding is Imagine Swimming's new venture that unites the passions of many of our staff and swimmers alike.  From diving into dropping in, from city pools full of water or completely empty, swimming and skating are sports full of similar creative expression -- and also activities where safety must come first.

"Safe Fun" has always been a core Imagine philosophy. We can't wait to bring that mindset to the skateparks and sidewalks of the city, as we teach interested children the fundamentals of the sport, with a focus on safety; the unwritten rules; and the rich history of skating in our city.

Much like Imagine Swimming's lessons, skate sessions are composed of small groups with no more than four children per instructor.

A big focus early on in your children's lessons will be to think before skating, or 'skating mental' in addition to basic balance and board manipulation, and how to safely negotiate the skatepark.  Once your new skater becomes more comfortable with basic techniques, we will introduce new skills.

We look forward to skating New York City with your children!


Spring Skateboard Lessons - Tribeca
Where: Pier 25 Skatepark


Duration: These 40 minute classes will be held at the following times on Wednesday-Sunday.



  • 3:20pm

  • 4:00pm

  • 4:40pm

  • 5:20pm

  • 6:00pm



  • 11:40am

  • 12:20pm

  • 1:00pm

  • 1:40pm

  • 2:20pm

  • 3:00pm


Spring Skateboard Lessons - UWS
Where: Riverside Skatepark


Duration: These 40 minute classes will be held at the following times on  Thursday

  • 4:00pm

  • 4:40pm

  • 5:20pm

  • 6:00pm




Regular Class: $40 per class. All scheduled lessons are billed monthly.
Semi-Private: $60/class, per child. All scheduled lessons are billed monthly.
Private: $120 per class. All scheduled lessons are billed monthly.



$50 (paid after trial upgrade). Billed annually.


Visit the parental portal, or Email for more information or to sign up


Imagine Skateboarding Decks are available now in our shop!



Josh was born in Springfield, Massachusetts to a family steeped in athletics. His father, Juhan, was an elite collegiate baseball player (at Springfield College he set the single season stolen base record) while his mother, Nancy, excelled as a gymnast. Josh's earliest memories were centered around dugouts and sidelines and in gymnasiums, where his dad coached and his mother judged college gymnastics. Swimming became a part of Josh's sport-centric upbringing when he joined the Pine Knoll Swim Team at age five. He went on to compete in age group competitions, excelling as a breaststroker and IM'er, and showed early talent when he placed second at the Western Massachusetts Championships two years in a row. However, he soon discovered skateboarding and by the time he reached high school he was gravitating more toward skating in empty pools than racing across filled ones! 

Josh recently left a two-decade career in the photo industry and, following in his parents' footsteps, has moved into teaching and coaching. As Imagine Skateboarding's first instructor, he hopes to share the lifelong joys of skating through Imagine's core philosophy of 'Safe Fun.' 


Chris Roche.jpeg
Christopher Roche

Born in New Jersey, and raised in Chile, Chris has always been interested in sports since he was a child. In his youth, Chris followed in his father's footsteps playing soccer for several years, and soon after picking up other team sports like basketball. Excelling in both sports, he even had the opportunity to participate in international tournaments in other countries.  However, it wasn’t until the age of 12 that Chris discovered his true passion of skateboarding. 20 years later, with skateboarding being his top sport, Chris can also be found snowboarding and surfing. Wanting to help others learn and grow within these sports, Chris has worked within the ski and snowboard industry for the past several years. He is excited to be working with Imagine Skateboarding to help pass along his love of skateboarding to the new generation.

Ray Romano

Ray first got into skateboarding  playing with Tech Decks during lunchtime in 7th grade with his friends. By summer break that year, he had saved up to buy himself a cheap skateboard, and he and his crew spent the summer learning all those tricks they dreamed about while playing with their Tech Decks in the lunchroom.

The cool auntie came through with a Powell Peralta Dragon complete next Christmas, but by the time Ray got to high school, that board had been relegated to the back of the closet.


The love of skating never left, and after graduation Ray picked up skating again. Not even a torn ACL in 2018 can slow him down now, and in fact he says he skates even better post surgery. 

As a veteran Imagine swim coach and deck supervisor, and one of our first skateboard coaches, Ray has helped to spread the Imagine ethos to all our new coaches, and can't wait to share his love for skating with everyone!

bottom of page