🎾 FREE Your First Session (60 min or less) Is On Me β€” No Catch Learn to Play sessions are always free
PCI Certified Coach Β· North Central Massachusetts

Pickleball Coaching with Jason Regan

Private lessons, group clinics, and free Learn to Play sessions β€” for players who want to get better, not just get more exercise.

Is Coaching Right for You?

Players Who Thrive Working with Jason

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Beginners Who Want to Start Right

Skip the bad habits. Learn footwork, kitchen rules, and the soft game from day one. Your future self will thank you. First session is free.

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Intermediates Stuck at 3.0–3.5

If you've plateaued, it's usually your third-shot drop or your kitchen game. We'll find the hole and fix it.

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Competitive Players Prepping for Tournaments

Pattern play, strategy work, and mental game prep. Show up at your next tournament with a real game plan.

How We Work Together

Programs & Pricing

πŸ“… Available Mon, Tue, Wed Β· 3:00 – 6:00pm Β· Primarily at Doyle Field, Leominster

Program Format Price
First Session β€” Free
Try it before you commit. 60 minutes or less, no strings attached.
1-on-1 · Up to 60 min FREE 🎾 Book Free
Private Lesson
One-on-one focused work on your specific game
1-on-1 Β· 60 min $40 Book
Group Clinic
Small group drills, games, and live coaching
4–8 players Β· 90 min $25/person Book
Learn to Play
Introduction to pickleball β€” rules, scoring, basic shots. Open to anyone.
Group Β· 60 min Always FREE Sign Up
Junior Pickleball Crew
Kids program β€” fun, fundamentals, and a love of the game
Ongoing program Contact for schedule Inquire
Partnership Learning Package
Two players coached together β€” perfect for spouses, doubles partners, or friends who want to improve as a team
2 players Β· 60 min $80 for 2 Book
Jason's Approach

Deception. Placement. Fast Hands.

"If you're trying to overpower opponents, you're already losing."

Jason is a deceptive player first. He lives for the dink, the fake, the perfectly disguised drive that leaves opponents guessing. Placement over power β€” always. The game is won at the kitchen line, not from the baseline.

And when the kitchen gets heated? That's where the fast hands come out. Jason loves showing off the net game β€” the speed-up, the counter, the reset. He'll teach you when to use each one.

You'll leave sessions with shots and a mindset. Both matter.

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Jason Regan
PCI Certified Coach
  • βœ“ PCI Certified Pickleball Coach
  • βœ“ USA Pickleball Ambassador Β· North Central MA
  • βœ“ Deception & placement specialist
  • βœ“ Fast hands at the kitchen line
  • βœ“ Available Mon–Wed, 3–6pm
  • βœ“ First session always free
  • βœ“ Learn to Play always free
What Players Say

Real Results, Real Players

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"Jason fixed my third-shot drop in two sessions. I finally understand what the kitchen game is supposed to look like."
β€” Local Player, Leominster MA
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"I was a total beginner. Jason made it fun, not intimidating. I'm already playing open play at Doyle Field and holding my own."
β€” Beginner Student
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"The group clinic was the best value I've found for pickleball instruction. Small group, lots of reps, real coaching feedback."
β€” Intermediate Player, Fitchburg MA
Always Free

Free Learn to Play Sessions

New to pickleball? Never even held a paddle? Learn to Play is for you. Jason runs free beginner sessions open to anyone β€” no experience required, no cost, no judgment.

In 60 minutes you'll learn the rules, how to score, and the basic shots. You'll leave ready to jump into open play.

  • βœ“ Completely free β€” always
  • βœ“ No prior experience needed
  • βœ“ Paddles provided if you don't have one
  • βœ“ Held at Doyle Field, Leominster
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Sign Up for Learn to Play

Email Jason to get on the list for the next session. We run them regularly β€” usually once a week when weather cooperates.

Sign Up β€” It's Free β†’

We'll reply with the next available date & time.

Before Your First Lesson

Not Sure Which Paddle Is Right For You?

If you're new to the sport or thinking about upgrading, our Paddle Finder ranks 741 paddles using side-by-side data from two of the most-respected reviewers. Take the 10-question quiz and you'll get your top 3 matches in under a minute.

Open the Paddle Finder β†’
Ready to Level Up?

Book a Session

Pick a time that works. Lessons held at Doyle Field (206 Priest St, Leominster) or a convenient North Central MA location.

πŸ“… Available Hours

Monday, Tuesday, Wednesday
3:00 PM – 6:00 PM

🎾 Your first session is FREE

Up to 60 minutes, no commitment. Just show up and play.

Questions first?
[email protected] Β· 508-808-4032

πŸ’³ Payment

Pay at the court β€” cash, Venmo, or PayPal all work. First session is always free, no payment needed to book.