10 Pickleball coaches & instructors for lessons in Holliston, 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!

"Charlie was excellent and helping me focus on drills regarding my play at the net in particular working on slowing down the game and using a softer touch with my paddle to help target more competitive play

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!

"I’m just a beginner looking to play mostly in a recreational sense and Ayann really helped me get started. He made the game easy to understand and really took his time and was patient with me as I was still learning the game.

Michael, based in Haverhill, MA, is a dedicated pickleball coach passionate about teaching across the North Shore of Massachusetts and Southern New Hampshire. With experience coaching players of diverse skill levels, he has helped students prepare for the Special Olympics, facilitated corporate team-building events, and guided individuals in improving their DUPR ratings. Michael specializes in coaching beginners to upper-intermediate players, focusing on skill development and a deeper understanding of the game, ensuring every session is both effective and enjoyable.

"The lesson was quite thorough with Michael maintaining constant engagement and focus throughout. His teaching skills really kept me involved, which made the whole experience quite insightful.

As a former tennis player turned passionate Pickleball enthusiast, I've transitioned my skills, technique, and strategy into the world of Pickleball. I play nearly every day and have dedicated extensive time to mastering the game. In addition to my racket sports background, I have experience teaching and coaching wrestling at the collegiate level. Now, my goal is to foster the growth of Pickleball and help individuals or groups enhance their skills, whether for casual play or competitive purposes. Looking forward to raising your game and having a blast on the court!

"Really, I gotta say, the lesson with Jon was quite helpful. He’s super knowledgeable and great at getting his lessons into your game. My girlfriend and I are taking the lessons together and we both felt like we learned a lot and had a good time. Jon has already helped me improve my transitions and soft game and helped her improve her drives and volleys. If you're aiming to sharpen your pickleball skills, you should consider giving Jon a try.

Phil Parrish is the award-winning Director of The Longfellow Clubs, where he leads a team of certified professionals in teaching pickleball across three locations in Wayland, Wellesley, and Natick. With over 15 years of experience in the tennis and pickleball industries, Phil is dedicated to helping players of all skill levels improve and enjoy the game. The Longfellow Programs offer a clear pathway for players to start at any level and progress in a fun, supportive environment. Phil and his team are committed to providing a top-tier pickleball experience, fostering both skill development and a love for the sport.

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.

Are you looking to take your pickleball game to the next level? I am an impact pickleball instructor that focuses on teaching you the whole game with s style of play that maximizes your full potential. I compete at the 4.5+ level myself and will teach you how to develop your technical, physical and strategic skills on the court.

If you are thinking about learning to play the fastest growing sport in the nation, but are hesitant to begin, read this short bio of our most popular Rhode Island instructor, Coach Phyl. Her experience and coaching style can help to ease your concerns. Hello and welcome! I’m Coach Phyl, and I am so glad you’re here. Let me tell you a little about why I love to work with beginning pickleball players. Pickleball is life, and I mean that literally. I took up the sport just as the Covid pandemic was shifting into high gear. It was the one thing I could do, despite my advanced age, while lockdown was beginning to happen all around me. It got me off the couch and moving, which I believe saved me from losing my mind, my passion for life, and my muscles, such as they are. It was kismet. I quickly recognized how similar the movements and strategies were to a game called Ace King Queen that I had played as a child. I loved and missed that game. Pickleball felt almost like finding it again. I fell in love with it immediately, not only for the game itself, but also for the social void it filled. Pickleball has brought many wonderful people into my life while providing me with a fun way to stay active during my “golden” years. I am filled with gratitude for all that it gives me, and I want to share these benefits with as many people as I can. We will have fun while you learn and practice new drills and skills. Pickleball is a multi-tiered sport that can be played by just about anyone. There is no better way to learn the basics than through in-person coaching. My teaching style is relaxed and non-confrontational. You will learn the rules of the game, proper warm-up techniques, paddle basics, a variety of strokes, serving options, targeting, timing, and the importance of drilling, with a few advanced strategies thrown in for good measure. As I like to say, just do it! There's no time like the present, so join me. See you on the court! Speaking of courts… While I am willing to travel to other courts, I encourage you to choose the courts at the John H. Chafee Sports Complex at 450 Hope Road in Western Cranston. These courts are well maintained and easy to get to. I love playing there, and I think you will, too. That said, if the weather calls for rain or otherwise is not in a cooperative mood (think wind, intense heat, snow, etc.), then a good choice would be the private indoor court at Open Table.

"Okay, I was pretty satisfied with the lesson with Phyllis. She paid close attention to my technique and offered useful tips that I can actually apply to my game. Still, I think I need a bit more practice, but I’m hopeful her guidance will help me improve. If you’re looking to refine aspects of your pickleball skills, you might want to give her a try.

With 5 years immersed in the vibrant world of pickleball instruction, I strive to develop well rounded players, I leverage my tournament-winning experience to impart not only technique but also a strategic approach to the game.gold medal over 50 champion in New Hampshire senior classic. He just competed in the U.S. Open 2025.