Ossining
Skateboard Lessons in Ossining
Learn to skate at Snowden Park Skatepark and along the Hudson River waterfront in Ossining.
Why Learn in Ossining
A Real Skatepark to Learn In
Ossining has something most Westchester towns don't: a public skatepark. The Snowden Park Skatepark has 4,200 square feet of ramps and features with areas that work for younger kids and separate sections for more experienced riders.
Waterfront Setting on the Hudson
Snowden Park sits in an 11-acre park along the Hudson River. Between the skatepark, the waterfront paths, and nearby Engel Park, there's no shortage of flat ground for beginners or features for students who want to progress.
Ossining is a river town of about 27,000 people on the east bank of the Hudson, roughly 30 miles north of Manhattan. The big draw for skating here is Snowden Park, which has one of the few public skateparks in Westchester County. The park is at 2 Water Street, right near the Ossining Metro-North station, so students coming from other towns can take the train and walk over in a few minutes.
The skatepark has multi-level ramps and enough variety that Leon can teach a first-timer on the flat sections and then move a returning student to the ramps in the same hour. The rest of Snowden Park has a basketball court, playground, and open green space along the river — so families with younger kids can hang out while a lesson is happening. Leon drives up from New Rochelle for Ossining sessions, usually about 40 minutes depending on traffic.
Where Lessons Happen
Leon teaches at the skatepark and waterfront parks in Ossining. Here are the main spots.
Snowden Park Skatepark
A 4,200-square-foot public skatepark at 2 Water Street with multi-level ramps and designated areas for different skill levels. Leon uses the flat sections for beginners learning to stand and push, and the ramps for students ready to drop in and work on transitions. The skatepark is inside an 11-acre park along the Hudson with parking nearby.
Engel Waterfront Park
Paved paths and open areas along the river with a relaxed atmosphere. Leon teaches here when students want flat ground to practice pushing, turning, and cruising without the ramps. A good alternative for younger kids or anyone who prefers open space.
Louis Engel Park
A larger waterfront park with paved walkways and open stretches near the river. Once students can push and steer confidently, this is a solid spot for practicing longer rides along the water.
What to Expect
Ossining has something most Westchester towns don’t: its own skatepark. Snowden Park’s skatepark is smaller and less crowded than the bigger regional parks, which makes it a good place for students ready to try ramps and transitions. For beginners, Leon starts on flat ground — the paths at Engel Waterfront Park give plenty of room to learn stance, pushing, and balance before moving to anything with a slope.
Each session is about an hour. Leon can provide a board if you don’t have one, though bringing your own is ideal. Flat-soled sneakers work best, and helmets are required for students under 18. If this is your first lesson, the beginner’s guide walks through what to wear, what to bring, and what the first session looks like.
Want to try it yourself?
Book a private lesson with Leon. NYC and Westchester, all ages and skill levels.
Lesson Rates
Leon travels to you. Board available if needed. No extra charge for travel in Ossining.
Want to skate regularly? See all lesson options — duo, monthly, and multi-session
What Students Say
“Leon is the best instructor! He makes you feel comfortable from the start.”
Kenny A.
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“Leon is so friendly, he effortlessly meets/makes new friends everywhere he goes.”
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Start Skating in Ossining
Book a private lesson with Leon at Snowden Park Skatepark or another spot near you.