Chestertown Parks & Playgrounds

Explore the natural beauty of Chestertown and surrounding Kent County by visiting one of our many parks or riding along one of our bike trails. Chestertown is a welcoming location for all visitors, even the four-legged variety who can enjoy our dog park!

Visit the Kent County Parks & Recreation website to see all the parks and facilities in Kent County.

Join our League

We play in the spring and fall, and we are always looking for new teams. You need at least 3 players at all regular season games. Games start at 6:00 in the spring and 5:30 in the fall and usually go around 1 hour. We play at the beautiful Wilmer Park in Chestertown. Visit the Ye Olde Town Bocce League website -


We want to hear from you! Please take a minute to complete our survey with your suggestions for our parks and playgrounds.


Special thanks to Sam Shoge at Shore Studios for use of his images.



The 18-acre park, located between Rolling Road and Schauber Road, is also home to the Chestertown Dog Park. Open Til Dusk Find Out More
Located on High & Cross Streets. Fountain Park is home to the Chestertown Farmers Market as well as community events. Open Til Dusk Find Out More
The Bayside Hoyas have adopted the Gateway Park basketball court located on Rt 20 and Flatland Road. Open Til Dusk Find Out More
Ajax Park on Cannon Street is a well-maintained community play area. Open Til Dusk Find Out More
Located at 402 E Campus Avenue the facilities are open to the public after school hours and when students are not present. Open Til Dusk Find Out More
Recently refurbished with new equipment and benches decorated by local students the park is dedicated to the memory of Louisa D’Andelot Carpenter. Open Til Dusk Find Out More
A waterfront park on Cross Street featuring the Broadreach Artscape at the entrance. Home to 4th of July fireworks and special events. Open Til Dusk Find Out More