Northern Bay Cruising: Places Worth Exploration by Sail
At a recent SpinSheet Crew Party I found myself discussing favorite anchorages with a few passionate sailors. Swan Creek in Rock Hall was mentioned, with several heads bobbing until one sailor admitted “Oh, I’ve never been north of the bridge.” That comment set off a cheerful exchange about the benefits of Northern Bay cruising, including being able to swim in waters without jellyfish.
For sailors who live south of the Chesapeake Bay Bridge, planning to cruise northern waters may require blocking off a week rather than a few days to enjoy the small towns and secluded anchorages. Those with shallower drafts will have more options, but there are plenty of destinations for deeper vessels. Here is a suggested Northern Bay itinerary, sailing up the Eastern Shore to the C&D Canal and back along the western shore.
1. Chester River
The Chester River winds more than 24 miles from its mouth to Chestertown and continues well beyond the town’s drawbridge. There are many coves to explore, including Lankford Creek, my favorite Chesapeake anchorage. We typically anchor near Cacaway Island in spacious waters on the east fork. Swimming is jelly-free along the scenic tree-lined shore. The sunsets are stunning. We’ve also anchored in the west fork depending on wind protection and have visited Lankford Bay Marina for fuel and pump out. Other favorite anchorages include Grays Inn Creek, Reed Creek, and the Corsica River.
One year we made it all the way upriver to Chestertown, taking a slip at the Chestertown Marina within view of the Schooner Sultana. Due to winding turns and the fickle nature of the wind, we had to motor all 24 miles. However, that annoyance was quickly forgotten when we explored the college town on foot, with its charming shops, art galleries, and restaurants, including the incomparable Modern Stone Age Kitchen. Cruisers can reprovision at Chester River Wine & Cheese, Chestertown Natural Foods store, or on Saturdays at the farmer’s market.
2. Swan Creek (Rock Hall)
We typically sail to Swan Creek at least once a season, taking a mooring ball at Swan Creek Marina or anchoring nearby. Rock Hall is a mile and a half away and is easily reached by bike or on foot. We often stop at a small beach before arriving downtown to have ice cream near the cottage vendors, sip coffee at Java Rock, or provision at Fresh Start Foods. On the return, we frequently stumble upon a waterfront festival, live music, or dine at Waterman’s Crab House. If venturing to Rock Hall seems too far, Swan Creek offers a few waterfront dining options in addition to simply grilling in the cockpit.
3. Fairlee Creek
I confess. We have never braved the shallow entrance and tricky currents to enjoy Fairlee Creek, but we have sailing friends whose sailboat draws six feet and swear that it’s worth the sweaty palms. Intrigued, I detoured to Great Oak Landing Marina during a recent Eastern Shore road trip to check it out. From shore, the approach appears as daunting as the charts depict, and yet the inside anchorage is scenic, spacious, and deep enough. There’s a beachside tiki bar (Jellyfish Joel’s) that boats will pass on their port after successfully navigating the narrow entrance. Dining and live music can be found at the marina, and transient slips are available for those who seek all the amenities. I look forward to visiting Fairlee Creek by boat someday, but I can assure you that I’ll be the sailboat approaching at slack on a rising tide.
4. Sassafras River
We’ve anchored in the scenic Sassafras several times. Before the pandemic, we enjoyed anchoring at Betterton and dining onshore, but sadly that restaurant has closed. However, for those who are willing to travel eight miles upriver, Georgetown offers stunning sunset views from the deck of the Deep Blue Restaurant at the historic Kitty Knight Inn. A couple of nearby marinas offer transient slips. Alternatively, about half the distance to Georgetown, there’s a decent anchorage at Turner Creek Bend, with access to a nearby park and pavilion.
5. Chesapeake City
We’ve passed through Chesapeake City several times while transiting the C&D Canal. We’ve only stayed overnight once, and that was a few years ago in the tight anchorage on the south side of the bridge. Concerned we were anchored too close to other boats, we discovered some friends who invited us for drinks in their cockpit and assured us our spacing was fine. Later, we caught a water taxi to explore the town and dine at the Bayard House, where we enjoyed a lovely meal, only to learn that the water taxi quit earlier than the posted hours. Yikes! Thankfully our friends generously responded when we phoned them at 9 p.m. (cruisers’ midnight) to ask for a lift home. Word to the wise: if you consider anchoring, the entrance has become shallower, so be sure to check depths and local knowledge.
6. Havre de Grace
This historic town on the western shore, which missed becoming our nation’s capital by just one vote in 1789, is one of my favorite places to visit. Yes, it’s another long passage, more than 10 miles from the Bay within a narrow but well-marked channel of the Susquehanna River. Those who visit Havre de Grace won’t be disappointed. We typically take a slip at Tidewater Marina, especially in the hot summer months when shore power offers air conditioning. Our favorite places to dine include Tidewater Grille with a view of passing Amtrak trains, MacGregor’s with live music, and La Cucina. Bombay’s Ice Cream is a great stop after a jaw-dropping visit to Washington Street Books & Music, which is sure to amuse young and old with its movie props. For those who need access to good coffee and internet, I’ve spent countless hours at Concord Point and Java By the Bay 2. Museum lovers will enjoy both the Maritime and Decoy Museums. And the distinguished skipjack Martha Lewis recently returned home to Hutchins Park after several years of restorations.
7. Magothy River
As sailors head south from Havre de Grace, there aren’t many adjacent rivers to explore on the western side due to shallow waters or busy powerboat traffic. When our sailboat was based in Baltimore, we occasionally anchored in Bodkin Creek or near Mike’s in Rock Creek. Then as now, we often ventured farther to turn into the beautiful Magothy River. I’ve lost count of how many times we’ve anchored in Broad Creek, within view of the contemporary glass house. When storms or high winds are forecasted, we often anchor near the horse farm in Eagle Cove, although it’s become quite crowded of late. When time allows, we sail farther up the river to Dividing Creek and Mill Creek.
As you see, there’s much to experience north of the Bay Bridge, in jelly-free water and on land. Whether you plan to loop the Northern Bay counterclockwise as described, or in reverse, or zig zag according to prevailing winds, the rivers and towns will leave you with lasting memories.
About the author: Captain Cheryl Duvall is a USCG Licensed Master, Inland 100 GRT, and is the program director for the Chesapeake Area Professional Captains Association (CAPCA). She sails the Chesapeake Bay on Belle Bateau, a Gozzard 44.
