Discover Chestertown with your Family

Kid-Friendly Activities

Discover Chestertown With Your Family

Welcome to our guide to kid-friendly activities in charming Chestertown, Maryland! Nestled along the scenic Chester River on the Eastern Shore, Chestertown offers a treasure trove of fun-filled adventures for families. From exploring historic streets lined with 18th-century architecture to enjoying waterfront picnics and educational experiences, Chestertown promises a delightful getaway for kids of all ages.

Wilmer Park

Wilmer Park serves as the hub for outdoor recreation in Chestertown. Located along the picturesque Chester River, the park features Aunt Sarah’s Playground, a modern art sculpture, chess tables, a pavilion, kayak launch site, kayak storage racks, a gazebo, benches, walkways, and a spacious open area. This versatile space is used for concerts, outdoor theater, bocce leagues, festivals, and a variety of other community events, making it a vibrant center of activity for residents and visitors alike.

Sultana Education Foundation

They offer programs and events that teach kids about the environment and history of the Chesapeake Bay region through hands-on activities and sailing experiences.

Kid Cutting with Scissors


KidSPOT is a hands-on creative learning center for children aged 2-12 open every Saturday free of charge to kids accompanied by their parents or other responsbile adult. The Center is a destination for area children where they can look forward to interacting with a variety of stimulating activities that expand their horizons.

Flagship Cinemas Seating

Flagship Cinemas

A trip to the movies is a fantastic way to entertain kids of all ages. From animated adventures to heartwarming family films, Flagship Cinemas offers a wide selection of movies that are perfect for young audiences. Treat your little ones to a big-screen experience they’ll never forget, complete with popcorn and their favorite snacks. Whether it’s a rainy day or you’re just looking for a special outing, Flagship Cinemas is sure to delight kids and parents alike!

Flagship Cinemas Seating

Self Guided Tours

The visitor center at the Kent County tourism office at 100 North Cross Street has information on self-guided walking, biking, and driving tours of the county, and a walking guide to the shady, brick streets of the Chestertown Historic District! Make sure to check out Twigs & Teacups, which will be sure to have a toy your kids will enjoy!

Ready for More Outside Play?

Chestertown is home to a variety of parks and playgrounds that are perfect for kids of all ages. From sprawling green spaces to playgrounds with exciting equipment, there’s something for everyone to enjoy. Click below to discover more family-friendly destinations in Chestertown!


Experience Chestertown’s colonial charm through our dedicated blog. Join us as we bring you firsthand accounts from enthusiastic visitors and passionate residents who have fallen in love with our historic town. Discover the hidden gems, explore the rich heritage, and immerse yourself in the stories that make Chestertown truly special. Stay connected and be inspired by the captivating narratives that unfold on our Chestertown Chat!

Upcoming Events

Chestertown is known for some long standing popular events that draw visitors from around the world! Enjoy Chestertown's year-round festivities from the weekly Farmers' Market to our Dickens of a Christmas in December! Join us for our next event, we promise good entertainment, good refreshments and great people!