
Over the past 18 months, I’ve taken the opportunity to combine business, vacation, and personal travel with…..you guessed it, pickleball.
Armed only with my “Places to Play” app, 2 paddles, 2 balls and my sneakers, I set out to test the premise that a fun pickleball experience can be found anywhere — even for a total stranger walking into a new town or community. I am pleased to report that I was 100% successful in each effort, and that the pickleball culture embraced me with open arms. Though there were a few snarky curmudgeons at some courts, the vast majority of people were friendly, and welcoming of ‘the new guy’. Sample places I’ve played in the past 2 years:
- Wilmington, Delaware (converted public tennis)
- *Chestertown, Maryland (YMCA)
- Fenway Park (yes, that Fenway Park)
- *Shaker Heights, Ohio (converted public tennis)
- Winnetka, Illinois (fancy country club)
- *Kauai, Hawaii (dedicated courts)
- *Pescadero, Mexico (converted local bball court)
- Cabo San Lucas , Mexico (resort tennis court)
- Tahoe City, California (converted public tennis)
- Incline Village, Nevada (indoor and outdoor community center)
- Groton, Connecticut (community center)
- Mystic, Connecticut (YMCA and Indoor Sports Center)
- Holly Hill, Florida (48 court dedicated pickle complex)
- Orlando, Florida (dedicated indoor in converted retail / warehouse)
- Wakefield, RI (4 court indoor converted warehouse)
- Wautoma, Wisconsin (outdoor public park using dropped tennis net)
- Stevens Point, Wisconsin (indoor sports center with newly designated pickle)
*Chestertown, Maryland
Eastern shore of Maryland……An unspoken condition for agreeing to visit my mother-in-law with my wife was that I be able to sneak away and find pickle. Sure enough, the brand spanking new Chestertown Y had no fewer than 8 courts lined out in their massive gym. My Connecticut Y membership got me in for free and I went several times for open play.
NOTES: Certain hours only, temporary nets, cool bleachers to watch play, 2 foot temporary fences between courts to restrain loose balls, informal round robin, players seemed to ‘self-level’ their groupings.
*Shaker Heights, Ohio
Cleveland suburb. Visiting my old college buddy who shares a recent pickleball obsession. His regular group meets at the recently converted local tennis courts at a middle school.
NOTES: Temporary nets, play can’t start til 9 am due to noise agreement with neighbors, stick your paddle in line in the chain link fence for rotation. Youngest player 11, oldest player 78. Great group
*Kauai, Hawaii

Our first ever trip to Hawaii and it was a challenge convincing my wife to leave beaches and hiking to play pickle, she has a bum shoulder and can’t play. But I succeeded by agreeing to visit botanical gardens (a good marriage involves creative compromises).
NOTES: I had 2 spectacular experiences. In Poipu Beach I played for the first time on 100% dedicated pickleball courts. So cool. In Princeville, a neighborhood of snowbirds had banded together to re-surface a local basketball court. Best view of my life from a pickleball court.
Both locations deployed the fairly standard ‘paddle rack’ rotation system to keep play flowing. Being Hawaii, both were used to out of town visitors.
*Pescadero, Mexico
Once again I had to negotiate a pass to leave my wife, daughter and grandchild to seek out pickle. This time in gritty inland Mexican village. Not a place I would have visited on my own but a google search revealed a Facebook page called “Pescadero Pickleball”. It hadn’t been posted on in a year but I took a shot and tried to find it. After driving through vegetable fields, sketchy looking farms and by roving chickens and stray dogs for miles, I suddenly heard the reassuring ‘plunk plunk plunk’ of pickleball.
NOTES: Snowbirds primarily from Seattle and Vancouver who stay at nearby resorts, had worked a deal with the town to convert their covered (thank god) basketball court to pickleball. AWESOME. Cost to play? 50 pesos ($2.98)
Each time we visit somewhere to play, we learn a bit more about this market! Pickleball Business Advisors is brothers Bill and John Pryor. We provide a variety of consulting services based on extensive experience in fitness business development, and research into the fast growing pickleball marketplace. To initiate a feasibility assessment for your pickleball club, or for other consulting, contact us so we can learn about your project.