Tarrytown
Skateboard Lessons in Tarrytown
Learn to skate along the Hudson River in Tarrytown and Sleepy Hollow.
Why Learn in Tarrytown
Quiet Paths Along the River
Tarrytown's waterfront and parks have smooth, paved paths without heavy foot traffic. That makes them good spots for learning to skate without worrying about crowds or obstacles.
A Relaxed Place to Start
There's no skatepark pressure here. Tarrytown's parks and open spaces give students room to learn at their own speed in a low-key setting that works well for first-timers.
Where Lessons Happen
Leon teaches at parks and open spaces in Tarrytown and the surrounding area. Here are the main spots.
Losee Park
A neighborhood park with flat, paved areas and enough space to practice without interruptions. Leon uses it for beginners working on balance and pushing, and for kids who want a calm spot to learn.
Patriots Park
Smooth paved paths wind through this park, making it a good fit for students who want to practice cruising and turning. Leon teaches here when students are ready to cover more ground.
Tarrytown Waterfront Area
Open pavement near the waterfront with flat surfaces and a relaxed atmosphere. A solid spot for first-time skaters or anyone who wants to learn in a scenic, low-traffic area.
What to Expect
Leon meets you at the spot and starts by finding out what you want to work on. First-timers learn stance, balance, and how to push. Returning students pick up where they left off, whether that’s turning, stopping, or learning their first trick.
Lessons are about an hour. Leon brings boards and helmets. Wear flat-soled sneakers and clothes you can move in. Helmets are required for students under 18.
Lesson Rates
All lessons include boards, helmets, and travel to your chosen spot in Tarrytown.
Private Lesson
$120
per hour
3-Lesson Package
$300
save $60
Group Lesson
$80
per person
What Students Say
“I've known Leon since 2016, in that time not only has he helped me tremendously in skateboarding skill he became one of my best friends. The patience and ability to break down tricks seems to come naturally to Leon. I've seen him teach people of shapes and size and ages and will 100% say he is worth your time!!!”
Raffi F.
Google Review
“Skating can feel intimidating. Leon creates a supportive environment and meets you exactly where you're at while celebrating the small wins.”
Paige W.
Google Review
Also Serving
Frequently Asked Questions
Leon teaches at Losee Park, Patriots Park (which has smooth paved paths), and the Tarrytown waterfront area. He picks the spot based on what you're working on and your comfort 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. Boards and helmets included.
Leon works with kids as young as four or five. He keeps sessions short and fun for the youngest students, focusing on standing on the board and getting comfortable.
No. Leon brings boards and helmets. Just show up in flat-soled sneakers and comfortable clothes. Bring water if it's warm out.
Yes. Sleepy Hollow is right next to Tarrytown and Leon covers both areas. If there's a better spot on the Sleepy Hollow side, he's happy to meet you there.
Fill out the form at leontoppin.com/book or text Leon at (914) 294-4407. He'll respond within a day to set up a time and meeting point.
Start Skating in Tarrytown
Book a private lesson with Leon at a park or waterfront spot near you.