Kids sitting on the grass

Local Events

Chestertown, a charming town located on Maryland's Eastern Shore, is a remarkable place for families looking to provide their children with a nurturing and enriching environment. With its idyllic setting, diverse community, and abundant educational and entertainment opportunities, Chestertown offers an exceptional quality of life for families. One of the biggest advantages of raising kids in Chestertown is the access to excellent educational institutions. The town boasts top-rated public and private schools, where children receive a quality education from dedicated teachers. These schools offer a wide range of academic and extracurricular programs, ensuring a well-rounded education for children of all ages. Additionally, nearby Chestertown is home to Washington College, a prestigious liberal arts college that provides countless educational resources and opportunities for residents. In terms of entertainment, Chestertown has a plethora of options to keep kids engaged and entertained. The town's vibrant downtown area features numerous family-friendly attractions, including parks, playgrounds, and recreational facilities. Families can enjoy biking along the scenic Chester River, exploring the expansive waterfront, or picnicking in one of the many picturesque parks. During the summer months, Chestertown hosts several festivals and events that cater to kids, promoting arts, music, and cultural activities. For educational opportunities beyond the classroom, Chestertown offers various museums and historical sites that provide an interactive learning experience for kids. The Chestertown River Museum is a popular destination, showcasing the region's rich maritime history. Additionally, the town's proximity to Baltimore and Washington, D.C. allows for easy access to world-class museums, science centers, and cultural institutions. Overall, Chestertown presents an ideal environment for families seeking a nurturing and supportive community for their children. With its outstanding schools, abundant recreational activities, and cultural offerings, Chestertown truly provides the perfect blend of educational and entertainment opportunities for kids.

Events in Chestertown

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28 results
Apr27-May189:15 AM
Yoga - Parent Child with Terra Spring II (ages 3 to 5) event image
May1616:30 PM
4th Grade Night Out to Shadow Land and RPYC event image
May1715:00 PM
Water Safety Day- FREE Family-Friendly Event event image
May1716:30 PM
Water Safety Day- FREE Family-Friendly Event event image
May1717:00 PM
Water Safety Day- FREE Family-Friendly Event event image
May1810:00 AM
Happy dancing parents draw
May1810:30 AM
Sensory Friendly Sundays event image
May2016:30 PM
Happy dancing parents draw
May2122:00 PM
Family Movie: "Despicable Me" Series event image
May2412:00 PM
Hometown Holidays 2025 event image
May2822:00 PM
Family Movie: "Despicable Me" Series event image
Jun1022:00 PM
Family Movie: Various Titles event image
Jun1410:00 AM
Children's Book Festival event image
Jun1413:00 PM
Expedition: Monarchs in our River-Friendly Yards event image
Jun277:00 AM
Happy dancing parents draw
Jul0614:00 PM
Family-Friendly Wild Soda Making with Lacey Walker event image
Jul12-150:00 AM
San Mar's The Great Bicycle Tour - TGBT XXXVIII event image
Jul120:00 AM
San Mar's The Great Bicycle Tour - TGBT XXXVIII event image
Jul2610:00 AM
Saturday Morning Kids – Guava Jelly event image
Kids on grass smilingWe help you save time and money
Kid running in baloonsWe bring families fun and entertainment
Kids playing at the kid`s playgroundWe are parent’s little helpers

Local Activities

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