These coaches teach at top ranked spots and have great lesson fulfillment & student reviews.
I’m a PPR certified instructor who has been teaching pickleball since 2022. Happy to work with you on game and stroke specifics or to teach you overall game strategy to get you on the courts!
"Honestly, Michael’s patience and overall teaching ability stood out to me during the lesson, though I think a bit more focus on specific techniques could help even more. Still, his calm approach really made me feel comfortable and motivated to keep improving. If you're looking for a coach who’s attentive and genuinely listens, I’d say give Michael a try.
Brent Weigelt is a PPR certified pickleball coach who helps players build real confidence on the court. You get clear instruction, simple drills, and feedback you can use right away. Brent focuses on footwork, strategy, and smart shot selection so you grow your game with purpose. His background in tennis and years in the pickleball community give you a coach who understands where you are and how to move you forward.
I combine my tennis background and coaching experience to help players master the fundamentals of power, placement, and purpose. My singles-based strategy training creates confident, adaptable doubles partners who know how to win from every position on the court. I focus on developing powerful serves, clean groundstrokes, and smarter point construction that improve shot selection and on-court decision-making. 🎾 “Points Planned with Purpose”
Igniting a love for the game is my mission. While relatively new to teaching, my deep understanding of pickleball strategy and technique allows me to effectively guide players of all levels. I'm dedicated to fostering a fun, supportive learning environment where you can reach your full potential.
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.
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 Chestertown 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.
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.
Private pickleball lessons in Chestertown average $71 for a week of lessons, with 1 vetted coaches available. Every session is private — 1-on-1 by default, or with your invited group — tailored to your level and goals, at a location and time that work for you.
Pickleball lessons in Chestertown happen at 3 locations across the city, from Kent County Middle School (Tennis Court) to lesser-known neighborhood spots. Bookings open up across weekdays, evenings, and weekend mornings — and if you have a preferred location, your coach meets you there.
Private pickleball lessons in Chestertown average $71 for a week of lessons. Booking a lesson package brings the per-lesson rate down, and one-off single lessons are also available — what you pay depends on your coach's experience and the session length you choose.
Private pickleball lessons in Chestertown are built around your goals. Whatever you want to improve, a coach can focus each session on it. Here are the areas coaches in Chestertown work on most.
Win at the kitchen line with controlled dinks, resets, and patience. Chestertown coaches build the soft game that decides most pickleball points.
Start each point on the front foot with a deep serve and return. A coach in Chestertown works on consistency, depth, and placement off both shots.
Master the third-shot drop and the transition to the net. Pickleball coaches in Chestertown teach when to drop, when to drive, and how to take the line.
Speed up the game, defend the body, and finish points at the net. Chestertown coaches sharpen your hands, reaction time, and shot selection up front.
Move as a team, cover the middle, and stay in the right spot on the court. Pickleball coaches in Chestertown drill footwork and doubles strategy.
Looking for youth pickleball coaching in Chestertown? We match kids and teens — from first-timers to high-school and club players — with coaches who specialize in junior development. Private youth pickleball lessons run at the same weekly rate as adult lessons.
Every coach who works with kids goes through identity and background screening before being matched with young students, and their safety vetting is shown on their profile — so you can book with confidence.
Coaches in Chestertown teach juniors from as young as 5 through high-school and competitive athletes, tailoring each session to your child's age, level, and goals — whether that is first-time fundamentals, building confidence, or tryout and team prep.
Parents are welcome to stay and watch — many do, especially with younger kids — but it is never required. Either way, your coach shares progress and what to practice between lessons.
The location with the most coaches teaching pickleball lessons at
Kent County Middle School (Tennis Court)
Number of certified coaches in Chestertown
1 certified coaches
Average length of time coaches in Chestertown have been teaching for
10 years on average
How many coaches teach pickleball in Chestertown
1 coaches
Average cost of a pickleball lesson in Chestertown
$71 for weekly lessons
Photo coming soon!
125 Park Ln, Chestertown, MD 21620
2.4 miles away • 1 pickleball coach teaches here
Photo coming soon!
300 Washington Ave, Chestertown, MD 21620
0.7 miles away • 1 pickleball coach teaches here
