If you haven’t yet explored the many miles of shoreline in Kent County, MD, here we share some boater-friendly trip suggestions for recreational boaters as well as anglers and paddlers on the Chesapeake Bay.

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Chestertown Marina. Photo courtesy of Kent County Economic and Tourism Development

The opportunities are plentiful because Kent County has water on three of its four “sides” (no, it’s not a perfect square). To the east lies the state of Delaware. To the north is the Sassafras River and Cecil County. The western edge is bounded by the Chesapeake Bay (which sets the scene for fabulous sunsets), and to the south is the Chester River and Queen Anne’s County. Inland Kent County is rural and relatively sparsely populated. If you go by car, you’ll see miles and miles of farmland. In addition to agriculture, the area is a popular waterfowl hunting destination.

With navigable waters on three sides, it is not surprising that the shoreline is dotted with marinas, beaches, parks, and fishing spots. Two public swimming beaches, one in the Town of Betterton and the other in the Town of Rock Hall, are owned and maintained by the county. Many marinas, full-service boatyards, dock bars, and water-view restaurants can be found along the waterfronts of the Bay and the Sassafras and Chester Rivers. 

Town of Chestertown

Chestertown, the waterfront county seat, is rich in colonial history. Walking tours are offered through the local Historical Society located on High Street. In addition to the restaurants and storefronts, you will find along the waterfront the Sultana Education Foundation home of the replica Schooner Sultana and host of the well-loved Downrigging Weekend Festival, which is held each fall and is one of the largest annual tall ship gatherings in North America. Chestertown is also home to Washington College. The 112-acre campus is dotted with stately red brick buildings and boasts a River and Field campus that is a living field lab developed to foster environmental projects.

If you’re in town on a Saturday, a massive farmer’s market on High Street runs weekly from the end of March until mid-December. Looking for a breakfast bagel or a sandwich lunch? Try Play It Again Sam, which is on Cross Street within walking distance of the river. For dinner try Phat Daddy’s Barbeque, which originated on the Western Shore and late last year opened “The Shack” on Spring Avenue. It is also within walking distance from the river, and as its name implies, serves up delicious barbeque and sides. Past visitors may remember 98 Cannon (previously Fish Whistle) on the waterfront. Unfortunately, it recently suffered a terrible fire and is currently closed until further notice. 

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Chestertown Marina. Photo courtesy of Kent County Economic and Tourism Development

Town of Rock Hall

The small town of Rock Hall sits right along the Bay, which means on clear evenings you’ll find gorgeous sunsets if looking out to the Western Shore. The public beach is a great place for viewing. Whether you’re into fishing, sailing, powerboating, or paddling, you’ll find this little town has lots of chartering options. Rock Hall has a long history of commercial crabbing, fishing, and oystering, so if you stroll down Main Street, stop into the Rock Hall Museum and learn more about the local economy and traditions. For those arriving aboard their own vessel, you’ll find multiple locations with transient slips. At the headwaters of Swan Creek, the well-protected Haven Harbor Marina has resort-style amenities and is home to the Waterman’s Museum, a tiny place that includes exhibits on oystering, crabbing, and fishing. Obtain the key from the adjacent Ditty Bag store.

Waterfront Camps

If your kids are looking for an overnight summer camp experience, Kent County has two good options: the YMCA Camp Tockwogh and the family-owned Echo Hill Camp. Located directly on the Bay near the mouth of the Sassafras River, Camp Tockwogh offers a weeklong specialty watersports camp designed for campers who want to focus on waterskiing, sailing, wakeboarding, and paddlesports (in addition to traditional camp offerings). Nearby Echo Hill Camp is situated on a 200-acre farm with a bluff sloping down to a long sandy beach. Here kids can try waterskiing, wakeboarding, kneeboarding, sailing, tubing, crabbing, fishing, kayaking, and boat rides, among other activities. The camp also has sunny fields, woodlands, and marshes.

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The view from Osprey Point Marina looking over The Haven off Swan Creek.

Cruising to and on the Sassafras River

By virtue of being in the Northern Bay, the Sassafras River has less salinity than those farther south, which makes this pretty waterway less appealing to sea nettles and hence more appealing to swimmers in the mid to late summer. The marinas and dock bars on the south shore offer plentiful destination spots for fishing, paddling, beach-going, or enjoying a cold drink and great food and conversation at a dockside bar.

Heading north from Rock Hall and hugging the Bay’s eastern shoreline you will continue around to the north side of Kent County. Here you might easily chart out an enjoyable multi-day cruise. Head northeast up the Bay. Along the way, you might plan stops at Tolchester, Fairlee Creek, Worton Creek, Still Pond, Betterton, and Georgetown. Bear right and ease into the Sassafras River. 

Before the mid-1900s, Tolchester Beach was for decades a popular vacation destination. Guests came by ferry or steamboat for the beach and amusement park. Today the beach is privately owned by Tolchester Marina. It remains a popular destination for boaters and swimmers due to its sandy beach and The Shanty Bar. Nearby, a trip up Fairlee Creek leads to the home of the well-loved Jellyfish Joel’s Tiki Bar. Safe Harbor Great Oak Landing also offers a marina, casual fine dining, a pool, and golf course. 

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Betterton Beach. Photo by Chris Cerino

Town of Betterton

Betterton Beach is a real gem. Located in the small town of Betterton, here you’ll find a five-acre, landscaped, family-oriented waterfront park. Situated near the mouth of the Sassafras River, the exceptional sandy beach has 300 feet of frontage for swimming and 700 feet of shoreline access. Along the waterfront area is a modern bathhouse with public restrooms, 500 feet of boardwalk with benches, and a picnic pavilion located on a bayview bluff. Anglers will enjoy the fishing jetty, and boating is available from a public landing and pier. If you’re looking for delicious food made with love, Marzella’s restaurant, run by Mr. and Mrs. Marzella, will deliver your order (made with fresh, high-quality ingredients), to the beach with a big smile and friendly conversation.

Turner’s Creek Park

As you make your way from the mouth of the river up to Turner’s Creek, keep your head up. There are lots of opportunities to spot wildlife, including bald eagles, along the cliffs that line both sides of the river. At the top of the creek is Turner’s Creek Park, part of the National Park Service Chesapeake Bay Gateways Network. It offers 147 acres of trails, woodlands, open fields, and a waterfront bluff overlooking Turner’s Creek. A public boat ramp and picnic pavilion are available. 

You may also want to explore the nearby Sassafras Natural Resource Management Area, which has fresh and saltwater ponds, wooded areas, farm fields, and trails. Knock’s Folly Visitor Center features exhibits highlighting the history of the farming community, the local Native American Tockwogh tribe, and Captain John Smith’s visit to the Turner’s Creek area.

Areas like Turner’s Creek and Lloyds Creek (just before Turner’s Creek as you head up the river) are great places to explore aboard paddlecraft, but this area is especially popular with paddlers in July and early August when the American lotuses bloom with incredible, giant yellow blooms that grace the surface of some of the shallower creeks and rivers in the area. 

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The shallow waters off the Sassafras delight paddlers each July with the American lotus bloom.

Top of the Sassafras

Boaters who make the trip all the way to the Route 213 Bridge will be rewarded with tranquil waters and multiple full-service marinas, including Skipjack Cove, Sassafras Harbor Marina, and Sailing Associates Marina. Fish Whistle at the Granary restaurant (previously located in Chestertown) offers waterfront dining in the warmer months and indoor fireside seating when it’s colder outside. Nearby, in Cecil County, the Mount Harmon Plantation is the northernmost colonial-era Tidewater plantation in the Chesapeake region that is currently open to the public. It’s designed for visitors to arrive by car, although the waterfront has a small dock. Those who pass by on the water will have a view of the old tobacco barn. Public tours teach about the history of the home, including commercial boat traffic on the Sassafras, which once was an important tobacco waterway. 

By Beth Crabtree