Pickleball Courts in Chestertown, MD
2 pickleball courts in Chestertown, MD — indoor and outdoor, free and paid. Verified counts, surfaces, hours and pricing. Updated 2026.
Kent County Family YMCA
Court count not yet published · Indoor · Membership Rating pending 02Roundtop Park
Court count not yet published · Outdoor · Free Rating pendingPlaying pickleball in Chestertown
We list 2 pickleball venues in Chestertown, MD.
On access, 1 is free public court and 1 is a membership club. Free play is your cheapest way in — start with Roundtop Park.
1 venue has courts under a roof, and 1 is outdoor-only.
Where to start
- Roundtop Park — Free to play, no membership required.
- Kent County Family YMCA — Indoor play when the weather turns.
Frequently asked questions
How many pickleball courts are in Chestertown, MD?
We list 2 pickleball venues in Chestertown.
Are there indoor pickleball courts in Chestertown?
Yes — 1 Chestertown venue offers indoor pickleball. Use the "Indoor" filter to see them.
Where can I play pickleball for free in Chestertown?
1 Chestertown venue is a free public court. Use the "Free" filter to find them.
Is the Chestertown pickleball court info verified?
Each listing is confirmed against the venue's own website or Google Business Profile; unconfirmed leads are clearly labeled "not yet confirmed." We never publish scraped data as fact.