Rye, NY
Skateboard Lessons in Rye
Private lessons for kids and adults at Rye Skatepark and outdoor spots around town.
Why Learn in Rye
A Skatepark Built for Learning
Rye Skatepark is small, and that's a good thing when you're starting out. The layout is compact with manageable features, so beginners aren't dodging experienced skaters across a huge park. It's the kind of place where a first lesson feels approachable.
Coastal Town, Easy Pace
Rye sits on Long Island Sound with a mix of families and commuters. The town's pace is a little slower than what you'd find farther south in Westchester, and that carries over to the skatepark. It's rarely crowded on weekday mornings and afternoons.
Rye is about 30 minutes northeast of New Rochelle, close to Port Chester and right on the Connecticut border near Greenwich. If you’re coming from southern Fairfield County, Rye is often closer than driving into the city. The Rye station on Metro-North’s New Haven line also makes it reachable without a car, which matters for teenagers and adults who don’t want to depend on a ride.
Leon’s Rye students tend to be a mix of local kids whose parents are looking for something outside the usual team sports, and adults from the area who want to learn on a board that’s not in the middle of a packed city park. The skatepark here works well for both. It’s small enough that a beginner can use most of the features within a few sessions, and quiet enough that you’re not competing for space.
Where Lessons Happen
Leon teaches at the skatepark and open spaces around Rye. Here are the usual meeting spots.
Rye Skatepark
The main lesson location. A compact park with quarter pipes, a small bowl section, and flat ground for fundamentals. Its size is an advantage for beginners because you can see the whole park from anywhere in it. Leon uses the flat sections for balance and pushing, then moves students to the features as they're ready.
Rye Recreation Park Area
Paved paths and open areas near the recreation facilities. Good for students who want flat ground and space to work on riding, turning, and building speed before stepping into the skatepark.
Your Driveway or Neighborhood
If you have a flat, smooth driveway or a quiet stretch of sidewalk, Leon can come to you. Some students, especially younger kids, are more comfortable starting at home before moving to the park.
What to Expect
Leon’s first question is always what you want to get out of the session. First-timers work on stance, balance, and getting comfortable with the board under their feet. Returning students pick up where they left off, whether that’s turning, dropping in, or cleaning up a trick.
Lessons are about an hour. Having your own board is encouraged, but one can be provided if needed. Wear flat-soled sneakers and clothes you can move in. Helmets are required for students under 18.
Lesson Rates
Leon travels to you. Board available if needed. No extra charge for travel in Rye.
3-Lesson Package
$300
save $60
Private Lesson
$120
per hour
Group Lesson
$80
per person
Want to skate regularly? See monthly and multi-session options
What Students Say
“Leon is one of the best skater/teachers in New York. He's very knowledgeable. And also very patient with his students. Skating is very difficult and there is a lot of repetition. He will be guiding you the whole way making sure you land trick.”
Bj M.
Google Review
“Leon is an amazing skateboarder and an amazing teacher. My son took lessons from him and it was amazing. It was very appreciative of how nice it was and how comfortable he made my son feel. I highly recommend him.”
Ms. Marie B.
Google Review
Frequently Asked Questions
Rye Skatepark is the main spot. It's compact and beginner-friendly, which makes it a good place to learn without getting overwhelmed. Leon also uses flat pavement and open areas around town when the skatepark isn't the right fit for a student's level.
Private lessons are $120 per hour. The 3-lesson package is $300 ($100 per session), and group lessons are $80 per person with a 2-person minimum. Board available if needed.
Leon works with kids starting around age four or five. For younger students, lessons are about getting comfortable on the board, standing, balancing, and moving at their own pace. Rye Skatepark's smaller size actually helps here because there's less to be intimidated by.
Yes. Rye station is on the Metro-North New Haven line, and it's a short walk or drive from the station to the skatepark and other lesson spots. Leon can meet you at a location that works with your commute.
Flat-soled sneakers and comfortable clothes. Having your own board is encouraged so you can practice between sessions, but Leon can provide one if needed. Bring water on warm days.
Go to leontoppin.com/book to fill out the booking form, or send Leon a text at (914) 294-4407. He'll reply within a day to lock in a time and place.
Start Skating in Rye
Book a private lesson with Leon at Rye Skatepark or a spot near you.