Chestertown MarylandBEACHES & WATERFRONT ESCAPES
Listed below are the best beaches and waterfront escapes near Chestertown, Maryland.
1. Ferry Park
BEACH WITH SUNSET VIEWS
Ferry Park is a hidden gem located down Rock Hall's Beach Road offering a swimming beach and gazebo with picnic facilities. Visitors can enjoy the water during the day and use the available picnic tables and barbecue stands for family meals. It's considered one of the best spots to witness spectacular sunsets over the Chesapeake Bay with outstanding views across to the Western Shore.
2. Betterton Beach
JELLYFISH-FREE BAY SWIMMING
Betterton Beach is a well-known 5.2-acre waterfront park featuring 700 feet of sandy shoreline along the Eastern Shore of Maryland. The beach offers amenities including a volleyball court, bathhouse, picnic pavilion, stone fishing jetty, and transient boat launching ramp. Located near the mouth of the Sassafras River, it boasts lower salinity levels than nearby beaches, making it completely jellyfish-free for safer swimming.
3. Tolchester Beach
HISTORIC BAY RECREATION
Tolchester Beach has a rich history as a popular summer destination where visitors once arrived by steamboat to enjoy attractions like a merry-go-round and roller coaster. Today, the area is home to Tolchester Marina which attracts boaters who come to enjoy the sandy beaches of the Chesapeake Bay. Visitors can learn about the area's past at the Tolchester Beach Museum before heading to the beach to enjoy swimming and sunbathing.
4. Chestertown Marina
DOWNTOWN WATERFRONT ACCESS
Chestertown Marina is a beautifully renovated port offering 15 transient slips up to 18 feet in depth within walking distance of downtown attractions. The marina, purchased by the town in 2011, underwent an eight-year transformation to create an inviting space for boaters. Though the waterfront restaurant is currently closed due to fire damage, a new dining establishment is expected to open by summer 2025.
5. Wilmer Park
RIVERSIDE FAMILY RECREATION
Wilmer Park is a waterfront recreational area located adjacent to Chestertown Marina along the Chester River. The park features a recently added playground with excellent equipment specifically designed for young visitors. This riverside green space offers families a perfect spot to relax and play while enjoying views of the water.
6. Rolphs Wharf Marina
SECLUDED WATERFRONT RETREAT
Rolphs Wharf Marina offers visitors a night of seclusion along the Chester River with comprehensive amenities. The marina features a ship's store, swimming pool, beach bar, and a charming bed and breakfast. It's an ideal destination for those seeking a quieter waterfront experience away from the bustle of town.
7. Sassafras Natural Resource Management Area
WILDERNESS WATER ACCESS
Sassafras Natural Resource Management Area provides a more natural beach experience near Chestertown. The area offers access to the Sassafras River with opportunities for swimming and wildlife observation. Visitors can enjoy the unspoiled natural beauty while experiencing the Eastern Shore's waterways in a less developed setting.
8. Conquest Beach
QUIET BAY ESCAPE
Conquest Beach is one of the best beaches near Chestertown offering a peaceful waterfront experience on the Eastern Shore. The beach provides swimming access to the Chesapeake Bay in a less crowded environment than some of the more popular destinations. Visitors appreciate the natural setting and opportunity to enjoy the water without the bustle of larger beach areas.
9. Shanty Beach Bar
BEACHSIDE ENTERTAINMENT HUB
Shanty Beach Bar is a palm-tree shaded waterfront venue located at Tolchester Marina offering live pop music and refreshments. The beach bar attracts visitors who come to enjoy summer celebrations along the sandy shores of the Chesapeake Bay. It serves as a modern gathering spot continuing the area's long tradition of waterfront entertainment that dates back a hundred years.
10. Barbara's on the Bay
WATERFRONT DINING EXPERIENCE
Barbara's on the Bay is a waterfront restaurant offering delicious meals with scenic views near Betterton Beach. The restaurant provides the perfect spot to relax and dine after a day of swimming and sunbathing at the nearby beach. Visitors can enjoy local cuisine while taking in panoramic vistas of the water, completing their beach day experience.