The Best Outdoor fun in Chestertown, Maryland

Chestertown Dog Park is a spacious and well-maintained park located at 100 Schauber Road in Chestertown, Maryland. This park is specifically designed for dogs to enjoy and socialize in a safe and secure environment. With separate areas for small and large dogs, as well as agility equipment and plenty of open space to run and play, Chestertown Dog Park is the perfect place for your furry friend to exercise and have fun. The park is conveniently located in a beautiful natural setting, making it a favorite spot for both locals and visitors to bring their beloved pets for a day of outdoor fun.

Wilmer Park is a popular outdoor destination in Chestertown, Maryland, located at 413 South Cross Street. This park offers a variety of amenities for visitors, including Aunt Sarah's Playground, modern art sculptures, a chess table, pavilion, kayak launch site, kayak storage racks, gazebo, benches, and walkways. The large open area in Wilmer Park is frequently used for concerts, outdoor theatre, bocce leagues, festivals, and other events. It is a beautiful spot along the Chester River where locals and tourists alike can enjoy nature and outdoor activities. Don't miss out on all the fun at Wilmer Park!

Welcome to Jellyfish Joel's Beach Bar, located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Our bar is not just a place to grab a drink, but a destination for boaters and beach lovers alike. At Jellyfish Joel's, we take pride in caring for your boat with passion and attention to detail. Our newly renovated on-premise accommodations offer comfortable rooms with amenities such as a mini fridge, private bathroom, and access to ice & coffee stations. Guests can enjoy free parking, free Wi-Fi, and access to the beach, outdoor pool, golf course, and more during their stay. The Lodge is open year-round and conveniently located for local events.

Happy Run Kennel is a premier dog boarding and training facility located at 301 Hoffecker Road in Chestertown, Maryland. Our experienced staff provides top-notch care and attention to all of our furry guests, ensuring they have a safe and comfortable stay while their owners are away. We offer spacious indoor and outdoor play areas, cozy sleeping quarters, and personalized training programs to meet the individual needs of each dog. At Happy Run Kennel, we strive to create a fun and welcoming environment for dogs of all sizes and breeds. Visit us today and see why we are the go-to destination for pet owners in Chestertown and beyond.

The Lelia Hynson Boating Park is a picturesque university located in Chestertown, Maryland, United States. This institution offers a unique opportunity for students to engage in hands-on learning experiences related to boating and water sports. With state-of-the-art facilities and a stunning waterfront location, students can explore the beauty of the Chesapeake Bay while gaining valuable skills and knowledge in the field of boating. Whether you're a seasoned sailor or a beginner looking to learn the ropes, The Lelia Hynson Boating Park provides a dynamic and enriching educational environment for all. Come and discover the endless possibilities that await you at this one-of-a-kind institution.

The Lodge at Great Oak Landing is a charming lodging facility located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Nestled in a picturesque setting, this institution offers guests a peaceful retreat with stunning views of the surrounding natural beauty. The Lodge provides comfortable accommodations, excellent amenities, and exceptional service to ensure a memorable stay for visitors. Whether you are looking for a relaxing getaway or a fun-filled vacation, The Lodge at Great Oak Landing is the perfect choice for your next adventure.