9 Pickleball coaches & instructors for lessons in Medway, MA

I'm a sports enthusiast who discovered a passion for pickleball in late 2022 after years of playing recreational tennis. Since then, I've fallen in love with the game and play almost every day. As a PPR Certified instructor and Six Zero Ambassador, I regularly drill and continually seek to improve my skills. As a 4.0 player, I'm dedicated to teaching others, helping them enhance their game, and spreading the joy of pickleball.

"The lesson with Larry was quite helpful, especially his helpful feedback and patience with applications. Though I think more technical details about shot mechanics would add to the learning, I’m hopeful that future lessons will cover this area as well. Still, I feel like I gained a good understanding of the basics, and it’s made me more confident in my game. If you're interested in steadily improving, Larry might be worth trying out.

Coming from a background in ping pong, Charley quickly became fond of pickleball during the tail end of COVID, gathering people from his church to play. Years later, as a World Pickleball Tour National Champion (January 2025) with a 4.5+ DUPR rating, Charley has reached the pinnacle of amateur competitive pickleball. With a Massachusetts teaching license and two years of coaching experience, he is passionate about helping players of all skill levels and age groups refine their techniques and develop a deeper love for the game. Additionally, he leads a weekly group and provides extra repetition with a ball-serving machine to maximize practice and improvement. Let’s take your pickleball game to the next level—let me know when you’re ready to get started!

"Charley was patient, knowledgeable and fun!

With two years of coaching experience and competing as a sponsored athlete, I bring a unique perspective to pickleball instruction. My passion is helping players of all levels unlock their full potential on the court. Let's elevate your game! Please message me about any inquiries, the more time I have to prepare the better as I also play in tournaments and so my schedule can fill up quick!

"Ayann really honed in on form and gave great tips for defensive strategy. Excited to my next 2 lessons- I think Ayann is really going to help me elevate passed 3.5

James Crosson has had the prestigious honor of being selected out of 300 participants to become one of the 60 certified coaches by DUPR’s exclusive coaching program. James is registered as National Professional Pickleball DUPR coach, a National Pickleball Professional with the International Registry of Pickleball Professionals, A National Professional with the International Coaches Institute, A professional with the RPPk Registery of Pickleball Professionals, and has worked with the Tyson McGruff coaching program to deliver excellence in all categories of coaching Pickleball. For over 8+ years James has become an avid Pickleball player, and his love for the game is only exceeded by his passion for teaching others how to improve in all aspects of their Pickleball game! From teaching beginners to excel quickly into the Pickleball world, to teaching advanced techniques and strategies to already established players to improve on their game, there is nothing James won’t be able to show you! James is extremely personable to make you feel comfortable in your learning process, and his methodology is that learning Pickleball should be a fun experience instead of feeling like a chore. James is an all-around athlete and has a strong tennis background from 6 years at the Newport Tennis Hall of fame. He fell in love with Pickleball, and was the founder of the very successful Fall River Pickleball Group. James is very competitive and is constantly playing in Pickleball tournaments against some of the best players in the Rhode Island and Massachusetts area. To ignite your passion in beginning your Pickleball journey, or to overcome the obstacles holding you back from being the best Pickleball player.

"James quickly taught me how to play so I could go out on the courts and start playing in open plays without feeling nervous! He gave me the ground work to start playing and learning on my own so I can continue to play until I need his guidance again! Awesome coach and fast teacher!

I love pickleball and the community it’s given me. Having learned from incredible mentors, I’m ready to pay it forward. A former 4-year HS tennis player, I’ve since competed in APA tournaments across all formats. My coaching is collaborative yet direct—I focus on technical skills to sharpen strengths and fix weaknesses. I offer flexible teaching tailored to what works best for you, always balancing improvement with genuine fun. All levels are welcome—let’s get on the court and level up!

I love the friendly environment that comes with playing pickleball, and I strongly believe that it is one of the most unique sports, due to its ability to be learned quickly without much previous experience. I’m extremely patient, can work with individuals at any skill level, and can tailor lessons to individual needs/goals. Most importantly, I love pickleball and bring this passion to any and all pickleball-related events. If you’re a beginner or have never even touched a pickleball paddle, within a short amount of time you’ll be able to rally and start winning points. If you’re more advanced, you’ll perfect you’re serve, spin, and net game. All ages and skill levels welcome!

"I found the serve practice to be especially valuable during the lesson with Daisy. It helped me focus on an important part of the game and improved my confidence on the court. If you want to sharpen your pickleball skills, I recommend giving Daisy’s lessons a try. You won’t be disappointed!

Ignite your passion for pickleball! With 25 years of coaching experience, honed by competing as a college athlete, I offer personalized guidance to elevate your game. My expertise ensures you'll achieve your goals while enjoying every moment on the court.

As a passionate pickleball enthusiast and experienced tennis coach, I bring deep understanding of strategy, technique, and player development to the game. With years of coaching high-performance tennis players, my transition to pickleball was a natural evolution - one fueled by a love for competition, community and continuous learning. A major emphasis will be placed on placing the trainee on a path of self discovery for developing the student's ability to solve problems independently.