Choose your session
Member prices are for members of The Pickle & Chilly Dill. Pick a program, choose your location and time, and you're booked.
A beginner-friendly introduction covering the fundamentals: rules, scoring, serving, positioning, and basic strategy. The goal is to help new players build confidence and feel comfortable on the court.
Book Pickleball 101Personalized instruction through live gameplay. Sessions focus on shot selection, court positioning, strategy, and technique, with real-time feedback. Saturdays, 10 AM–12 PM.
Book Dinkin'A structured session for players ready to take their game to the next level: targeted drills, advanced strategy, technical development, and competitive play. Same price for members and non-members.
Book Advanced TrainingOne hour built around your level, goals, and the parts of your game you want to improve, from fundamentals to tournament prep. Lessons away from The Pickle depend on distance and availability; you cover any court fees there, and travel charges may apply. Dylan confirms any extra cost before you book. Packs expire one year after purchase.
Book PrivatePrivate lessons
One-on-one coaching built around your level, goals, and the parts of your game you want to improve. Buy a pack and save.
Lessons held at the facility
| Lesson | Members | Non-members |
|---|---|---|
| Single lesson (1 hour) | $70 | $80 |
| 4-pack (1 hour) | $260Save $20 | $300Save $20 |
| 8-pack (1 hour) | $500Save $60 | $580Save $60 |
| 12-pack (1 hour) | $650Save $190 | $800Save $160 |
Independent coaching
| Lesson | Price | Savings |
|---|---|---|
| Single lesson (1 hour) | $60 | — |
| 4-pack (1 hour) | $220 | Save $20 |
| 8-pack (1 hour) | $420 | Save $60 |
| 12-pack (1 hour) | $600 | Save $120 |
Player development programs
Private lesson packages with an assessment, a plan, and video review, all tailored to your skill level, goals, and areas for improvement.
Build your foundation
5 private lessons$399
A great starting point for players who want to build a strong foundation and develop confidence on the court.
Train with purpose
10 private lessons$799
A comprehensive program for players who are committed to taking their game to the next level, with a structured plan and ongoing feedback.
Elevate your game and your gear
10 private lessons$999
The full development experience: everything in Complete Player Development, plus a personalized paddle consultation and one paddle tailored to your game.
All lessons must be completed within one year of purchase. See the cancellation policy above.
Clinics & events
Dylan runs special clinics and events a few times a year. Want to hear about the next one? Send him an email.
Brand new? Start with Pickleball 101. If you play regularly and are around 2.5–3.5, try Dinkin' With Dylan. 3.5 and up, join Advanced Training. Want to work on something specific? Book a private lesson.
Sessions at The Pickle & Chilly Dill are paid at the court, with no online prepayment. Private lessons at other locations may require payment in advance.
Not at The Pickle & Chilly Dill. For private lessons at another facility, you cover any court fees there, and travel charges may apply. Dylan confirms any extra cost before booking.
Group sessions are at The Pickle & Chilly Dill, 3350 E Montclair St, Springfield, MO. Private lessons can also be held at other courts, depending on distance and availability. You choose your location when you book.
Cancel or reschedule more than 24 hours before your session. Late cancellations or missed sessions may forfeit the session or its fee. Exceptions can be made for emergencies at Dylan's discretion.
Yes. Lesson packs expire one year after purchase.
No. Dylan has demo paddles and balls from LUZZ, Friday, SixZero, and 11Six24 for you to use, so you can try different gear before you buy.
Comfortable athletic clothes and court shoes with non-marking soles. Bring water.
Booking
Pick a program, a location, and a time. Sessions at The Pickle & Chilly Dill are paid at the court.
