TeachMe.To Logo

The easy way to learn to play.

AboutFAQCoach FAQHelp Center
BrowseReviewsPrivacyTerms
InstagramFacebook

© 2026 Teach Me To


As a platform, we do our best to provide accurate information and make your booking experience seamless. However, we do not verify every detail and we do not background check every coach who lists themselves on our site. It's up to the instructors to provide accurate, up-to-date information. If you have any questions or concerns, just message us and ask!

💙
Get a free trial lesson
How does it work?
💙

Get a free trial lesson

First lesson free
•
Pay 24 hours after trial
•
Cancel anytime
TeachMe.To LogoTeachMe.To Logo
•
Near
Ossining
•
Near
Ossining

Best 2 coaches for Pickleball lessons near Ossining, NY

These coaches teach at top ranked spots and have great lesson fulfillment & student reviews.

These coaches teach at top ranked spots and have great lesson fulfillment & student reviews.

Don Dilorenzo profile
Don Dilorenzo photo 1
Don Dilorenzo photo 2
See more photos on profile
About Don

Don DiLorenzo – Certified Pickleball Instructor I’m a PPR-certified pickleball instructor with over 4 years of coaching experience, working with players of all ages and skill levels—from brand-new beginners to advanced competitors. My goal is to make learning fun, approachable, and tailored to each player’s unique style and goals. Whether you’re looking to build a strong foundation, fine-tune your technique, or develop winning strategies, I offer clear, supportive instruction that helps you grow your game with confidence. I specialize in fundamentals, court positioning, shot selection, and game IQ—while keeping sessions dynamic, safe and engaging. Let’s get you playing smarter, faster, and with more enjoyment every time you step on the court!

What students say...

"Don is an excellent choice for seniors looking to learn or improve at pickleball. He understands the limitations of people that are slightly older like myself. He focuses on fundamentals, puts safety 1st and explains how to play smarter not harder while creating a relaxed, welcoming environment. Players feel supported and comfortable at every level. Keeps the fun in the game.

Best Price
✨New
Don
From$93per lesson

Don

Bio: Don DiLorenzo – Certified Pickleball Instructor I’m a PPR-certified pickleball instructor with over 4 years of coaching experience, working with players of all ages and skill levels—from brand-new beginners to advanced competitors. My goal is to make learning fun, approachable, and tailored to each player’s unique style and goals. Whether you’re looking to build a strong foundation, fine-tune your technique, or develop winning strategies, I offer clear, supportive instruction that helps you grow your game with confidence. I specialize in fundamentals, court positioning, shot selection, and game IQ—while keeping sessions dynamic, safe and engaging. Let’s get you playing smarter, faster, and with more enjoyment every time you step on the court!
5.0
5 Lessons given
5.0
Nearby
2.1 mi
Chilmark Park
Available
Next: Tomorrow, 8:00 AM
💰$93 for weekly lessons
Get pickleball lessons with Don
Happy Student Score
What's the Happy Student Score?Coaches get a 0–100 score reflecting their reliability, responsiveness and customer satisfaction.
Learn more
Learn more
Chris Novelli profile
Chris Novelli photo 1
Chris Novelli photo 2
See more photos on profile
About Chris

Driven by a lifelong passion, I bring several years of pickleball coaching experience to help you elevate your game. My approach blends strategic insight with personalized techniques for lasting improvement and on-court confidence. Let's unlock your full potential!

What students say...

"If you’re looking for a coach who is both easy to get along with and highly skilled, Chris is the one. He brings a contagious energy to the court, and it’s clear he clearly loves the game. I really appreciate how he adapts his teaching style, to my needs, using fun drills that keep me motivated while noticeably improving my game. It is a huge plus that he’s such a strong player himself; his demonstrations are always spot on!

✨New
Chris
From$100per lesson

Chris

Bio: Driven by a lifelong passion, I bring several years of pickleball coaching experience to help you elevate your game. My approach blends strategic insight with personalized techniques for lasting improvement and on-court confidence. Let's unlock your full potential!
5.0
5 Lessons given
5.0
Nearby
2.1 mi
Chilmark Park
Available
Next: Tomorrow, 8:00 AM
💰$100 for weekly lessons
Get pickleball lessons with Chris
Happy Student Score
What's the Happy Student Score?Coaches get a 0–100 score reflecting their reliability, responsiveness and customer satisfaction.
Learn more
Learn more
  1. Pickleball
  2. New York
  3. Ossining
Featured in
Featured in

Finding a pickleball coach in Ossining is simple

1.

Find the right pickleball coach in Ossining.

We help you find the best pickleball coach for your needs. Filter by skill level, group size, and location. Browse our list of pickleball coaches that meet your criteria and watch their intro videos to determine if the coach is the right match for you. Our pickleball coaches are vetted, reviewed, and rated to make your decision easier. If you're having trouble finding the best pickleball lessons near you, reach out to our lessons coordinator by clicking the "Have any questions?" button at the top right of the page.

2.

Schedule your pickleball lesson in seconds.

Unlike other websites, TeachMe.To lets you schedule your pickleball lesson time and location online in seconds. We make the whole process seamless. Other websites for finding Ossining pickleball lessons and coaches make it hard to book and have very little information on pricing and scheduling. Not with us: we make it easy to find the right date, time, and place to learn pickleball.

3.

Instantly connect with your pickleball coach.

Get in touch with your pickleball coach immediately with the TeachMe.To mobile app. It's total free and available on iPhone and Android. Our app is the one-stop shop for managing your pickleball lessons on our platform. Communicate with your pickleball coach, get notified about new messages, view and manage upcoming pickleball lessons near you, track your progress, and get access to support services - all in one place.

It's really that simple.

Frequently asked questions

Also available in Ossining

Basketball lessons in Ossining
Tennis lessons in Ossining
Soccer lessons in Ossining
Golf lessons in Ossining
Singing lessons in Ossining
Baseball lessons in Ossining
Boxing lessons in Ossining
Volleyball lessons in Ossining
Dance lessons in Ossining
Guitar lessons in Ossining
Piano lessons in Ossining
Violin lessons in Ossining
Flag Football lessons in Ossining
Mental Health lessons in Ossining
Personal Training lessons in Ossining
Softball lessons in Ossining
Lacrosse lessons in Ossining