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Cape Cod Pickleball at Chequessett Club

Cape Cod’s Most Social Sport

Pickleball has taken Cape Cod by storm — and the Chequessett Club is at the center of it all. Whether you’re picking up a paddle for the first time or competing in team matches against other clubs, we have clinics, open play, social events, and junior programs running all summer long. All sessions are bookable online through CourtReserve.

4 Courts

Dedicated Pickleball · Members & Public

8 Programs

Clinics, Open Play & Competitive

All Levels

First-timer to Tournament Player

All Members can book through the Pro shop or organize play through TeamReach — use code 9291 for the Chequessett Group. All weather-related cancellations and postponements are posted there.

Reserve Court Now

Community & Fun

From casual open play to Dinks & Drinks socials, pickleball at Chequessett is as much about great company as great play.

Clinics for Every Skill

Pickleball 101 for first-timers, Beginner and Intermediate clinics for developing players, and advanced Drill & Play for the competitive set.

Compete All Summer

Team Play events pit Chequessett against other Cape Cod clubs. Junior clinics bring the next generation of players onto the court.

Daily Pickleball Activities

Summer 2026  •  Advanced registration required via CourtReserve

Clinics & Programs

Structured instruction for players looking to build and sharpen their game

Clinic

Pickleball 101

For players brand new to the game. Learn essential shots, serving techniques, and scoring basics.

Mondays | 8:00am – 9:15am

Member: $20
Non-Member: $35

Register Now

Clinic

Beginner Pickleball

Sharpen shot selection and match play. Drills followed by moderated match play for the novice player.

Wednesdays | 11:00am – 12:00pm
Fridays | 8:00am – 9:15am

Member: $20
Non-Member: $35

Register Now

Clinic

Intermediate Skills & Drills

Enhance your game beyond beginner level. Drills focus on serves, dinks, drives, and match play scenarios.

Wednesdays | 10:00am – 11:00am

Member: $20
Non-Member: $35

Register Now

Clinic

Drill & Play

For advanced players with match and tournament experience. Fast-paced drills followed by moderated match play.

Tuesdays | 4:30pm – 6:30pm

Member: Free
Non-Member: $20

Register Now

Open & Social Play

Drop-in play, social events, and fun on the courts — open to all

Open Play

Pickleball Open Play

Fun, engaging drop-in play to master your skills and enjoy the game with friends.

Wed & Sat | 8:00am – 10:00am
Mon & Fri | 10:00am – 12:00pm

Member: Free
Non-Member: $20

Register Now

Social

Dinks & Drinks

Two hours of moderated round robin mixed doubles followed by drinks at the boathouse. The week’s highlight!

Thursdays | 3:00pm – 5:00pm

Member: Free
Non-Member: $20

Register Now

Competitive & Junior

Team match play and programs for younger players ready to compete

Competitive

Pickleball Team Play

Competitive intra-club and inter-club matches against other Cape Cod clubs. Team format with match play at multiple levels. Match play experience required.

Sundays | 3:00pm – 5:00pm

Member: $20
Non-Member: $35

Register Now

Junior

Junior Pickleball Clinic

For younger players ready to learn the game. All levels welcome — drills followed by match play. HS & College players encouraged.

Sundays | 1:00pm – 3:00pm

Member: $20
Non-Member: $30

Register Now

Pickleball Events

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