Discover the Upper Chesapeake Bay by Sailboat

Cruising the Northern Chesapeake Bay

“Venturing north of the Bay Bridge brings a different kind of fun and challenge for cruising sailors on the Chesapeake. Shallow water, brown water, but also fresher water, and fewer jellyfish are among the obvious. The bridge itself is something of a gateway, or barrier, depending upon how you look at it,” contributing SpinSheet writer Steve Allen once declared. And he’s spot on. Sometimes Middle and Southern Bay sailors wonder whether the Upper Bay is really sailboat- and sailor-friendly. Our sailing friends who know the area well tell us the Upper Bay has much to offer.

The catboat Planet at sunrise on the Upper Chester River, a tributary of the Chesapeake Bay. Sailboat photo courtesy of Craig Ligibel

Certainly, it is true that some areas are busy with powerboat traffic on hot summer weekends. The Middle, Bush, Magothy, North East, and Sassafras Rivers come to mind, as do popular gathering spots around Dobbins and Hart Miller Island and Fairlee Creek. But don’t let that deter you from exploring the region by sailboat.

Bryant Gorrell, a sailor, powerboat owner, and longtime resident of the Upper Bay region, who also serves as cruising director for the North Chesapeake Cruising Club, says, “There are many interesting places in the Upper Bay that can be explored by sailboat. Some are quiet with lots of birds and wildlife, others have interesting things to see and do.”

Gorrell, who sails a Catalina 30 with a three-foot, 10-inch draft, suggests checking out the Upper Chesapeake Sailing Facebook group for local knowledge. ”It’s a great group for information,” he says. “We have approximately 1200 members, so if you post questions about water depths, how well anchors hold in certain anchorages, or marina suggestions, for example, you’ll usually get some really good sailor-specific answers. Even though I sail up and down the Upper Bay and know the rivers and creeks well, there are still some areas that I wouldn’t choose to go with my sailboat,” he says.

Havre de Grace, Maryland, on the Chesapeake Bay is a popular destination for sailors. Photo by Adam Rybcznski

Havre de Grace

At the top of Gorrell’s list of places to visit is the town of Havre de Grace, MD. “Havre de Grace is an historic town with plenty of neat little stores, street fairs, nice marinas, and deep water in the channel. The July 4 parade is terrific, and in August and September the first Friday street festivals will return.” Havre de Grace’s shoreline has a beautiful waterfront promenade that ends at the Concord Point Lighthouse and Keeper’s Museum, where the Susquehanna River meets the Bay. The Maritime Museum and Lock House Museum will also be of interest to most sailors.

Chesapeake City

“Another interesting place to visit at the top of the Bay is Chesapeake City,” says Gorrell. “The town sits along the C&D Canal, and a hiking and biking trail runs along the water. Early fall is a great time to be there because you can watch, and sometimes meet, the many transients heading south to Florida and the islands. Some have fascinating stories. If you enter the canal by boat, be aware of the strong current, which can run from one and a half to two knots. Timing is crucial.”

Pirates and Wenches Fantasy Weekend in Rock Hall, MD, is an annual destination for many cruising sailors on the Northern Chesapeake Bay. Photo by Charles Milsop

Rock Hall and Swan Creek

The town of Rock Hall makes an excellent sailing destination. There’s plenty to do, with great waterfront fun and dining at the local restaurants and carry-out options to take back to the boat. The community has a real sailing vibe, public docks, many marinas, and generations of local waterman call this place home. Boat yard services, sailmakers, and charter (fishing and sailing) are part of the fabric of this community.

SpinSheet editor Molly Winans says, “As much as I can enjoy the party vibe on the dock by Waterman’s Crab House on a Saturday night at Rock Hall, MD, I appreciate the rural aspects of the Eastern Shore. Swan Creek is the quiet side of Rock Hall. It’s not for every sailor (check your depth in advance), but if you’re lucky enough to have a multihull or shallow draft sailboat, this calm creek with traditional shore scenery (barns, horses) makes for a wonderful place for a sundowner and a good night’s sleep. If you prefer a marina, look into Spring Cove or Haven Harbour for slips on the creek. There are also mooring balls available at Haven Harbour.”

Kayakers explore the American Lotus Blooms on the Sassafras River, a tributary of the Chesapeake Bay. Nearby is the historic Mount Harmon Plantation.

The Sassafras River

If you plan your visit to the Sassafras River in mid-July to early August, you may be in for a treat. This is the time of year that the amazing American lotus blooms appear in a couple of the creeks here. On the north side of the river the historic Mount Harmon Plantation even sponsors a Lotus Blossom Festival to celebrate the blooms. When you are ready to head to town, two historic towns can be found along the river, Georgetown and Fredericktown on opposite shores where the Route 213 bridge crosses the river. If you’re looking for a slip or marina services, Skipjack Cove Yachting Resort and Georgetown Yacht Basin with its associated Granary Marina provide plenty of amenities and dining for sailors and boaters. For overnight anchorage, Gorrell suggests Turner Creek, on the south side of the river. If it’s a hot summer day, SpinSheet centurion Davel Nestel reports that the Sassafras is a great river for swimming.

Still Pond and Worton Creek

Winans recalls her first trip to Still Pond, south of the Sassafras River, “Still Pond was such a pleasant surprise as a cruising destination. We first went there because, with a draft of six and a half feet, we feared the skinny entry to Worton Creek just to the south of it. We had no expectations and were pleasantly surprised. It’s an open anchorage, not the most protected one if you’re anticipating heavy weather, but perfect for a calm summer’s night. It’s not a secret. Expect other sailboat and powerboat cruisers, as well as families playing on water toys closer to shore. Bring kayaks and paddleboards and join the fun! The greatest joy of this anchorage is paddling into Still Pond Creek or Churn Creek (both with shallow entrances, sandbars at low tide), which open up into a whole new watery world to explore.”

As Winans noted, Worton Creek does have a narrow entry, but it is still a favorite for many sailors. Gorrell says once you navigate the entry, the water widens to expose “a special little place where we often see bald eagles—not a huge anchorage, but a peaceful one and a good weather hole.” Worton Creek Marina, located just 1.5 miles off of the Bay, offers a beautiful and tranquil setting, with all the amenities.

A family owned and operated business since 1949, slips can be reserved using Snag-A-Slip.

Sailors eating crabs at Kennersley Point Marina, on South East Creek off the Chester River, a tributary of the Chesapeake Bay. Photo courtesy of Craig Ligibel

Chestertown and the Chester River

With a shoreline dominated by agricultural land dotted with small towns, the Chester River is another scenic cruising destination. You’ll not find many options for fuel or much of a dock bar scene, but if you are looking for beautiful shores and some nice anchorage spots, you’ll find them here. Chestertown, probably the most well-known town on the river, is home to Washington College, the Schooner Sultana, and quiet streets that beckon a leisurely stroll. The town, most of which tends to be dog friendly, is home to two well-known festivals, which are perennial favorites for many sailing cruisers—the Chestertown Tea Party on Memorial Day Weekend and Sultana Downrigging Weekend around Halloween. History, tall ship, and pirate aficionados will be in nirvana at these two events. 

Baltimore Harbor and skyline. If sailing on the Pataposco River, look for the red, white, and blue buoy marking the spot where Francis Scott Key wrote the Star-Spangled Banner. Photo by Adam Podbielski

Baltimore Harbor

Baltimore Harbor is a completely different experience from the other spots we’ve covered, but it offers all kinds of opportunities. From Fort McHenry to the National Aquarium, to professional baseball and football games, and outdoor concerts, there is much to do within walking distance of the marinas along the Inner Harbor. A waterfront promenade provides a great place to get off the boat and stretch your legs. Many delicious restaurants are easily within reach.

As you navigate the waters of the Patapsco River near the Francis Scott Key Bridge, keep an eye out for the red, white, and blue buoy that marks the approximate place where Key penned the words to the Star-Spangled banner during the War of 1812. You can find lots of slip choices at Baltimore marinas using Snag-A-Slip.

~by Beth Crabtree