The waters between the twin spans of the Chesapeake Bay Bridge and Havre de Grace, MD, are often overlooked as “too remote” with towns that some say are spaced too far apart to cruise comfortably. But if you haven’t explored this less-developed part of the Bay, you should. The area is characterized by wide, open, brackish, tree-lined tributaries with sections of sandy beaches. The rivers are sparsely punctuated with development—aside from the occasional marina or small town—and the smaller creeks branching off from the bigger tributaries beg exploration, especially in great fall weather. We’ll start this adventure at the north end of the Bay in Havre De Grace and work south, but you can reverse or alter the route. There are great destinations in between, including the town of North East, the Bohemia River, Still Pond, Worton Creek, Fairlee Creek, and Chestertown—but here is one of many four-day itineraries to try.
Top o’ the Bay Havre de Grace (NOAA Charts 12270, 12278, and 12274)
Havre de Grace sits at the mouth of the Susquehanna River, which contributes the largest share of fresh water to the Chesapeake among all the Bay’s tributaries. It’s about 38 nautical miles up the Bay from the Chesapeake Bay Bridge at Sandy Point and Kent Island, and despite the sometimes heavy ship traffic heading to and from Baltimore Harbor and the Chesapeake and Delaware Canal, it’s an easy run on a well-marked route.
One area that demands attention on your way north is the charted magenta area around Aberdeen Proving Ground (APG) starting at Pooles Island near flashing green buoy “7” and running all the way up to the northern tip of Spesutie Island at flashing green buoy “3.” Don’t be surprised if you get rocked by loud “booms” that shake your boat while cruising near the area—it’s a munitions testing area. Yellow nun buoys outline the warning area. If you happen to stray into the restricted area, a U.S. Army patrol vessel will quickly pay you a courtesy visit. A winding channel works its way up past Spesutie Island past some spoil islands toward town; if you stay in the marked channel, you shouldn’t encounter any problems.
At flashing green buoy “17,” you can either turn to the west and into the marked channel leading into the City Yacht Basin at Millard E. Tydings Memorial Park (Commerce Street and South Washington Street), or north toward the several marinas that line the waterfront end of town. Check a cruising guide for details on specific amenities at area marinas, and secure reservations for an overnight stay in advance.
There is an open and exposed anchorage located just off the town waterfront outside of the marked channel, but stay clear of the mooring area. In town, you’ll find shopping, restaurants, and a promenade at the park with an unimpeded view across the river and down the Bay. The town is probably best-known for its decoy carving heritage. Stop by the Havre de Grace Decoy Museum at 215 Giles Street (410) 939-3739) to learn about the history behind this craft that was once a necessity for hunting waterfowl. Several antique shops around town also deal in decoys. Also consider the Havre de Grace Maritime Museum at 100 Lafayette Street. Restaurants line the town’s main drag.
Wind Down and Slow Down in Georgetown (NOAA Chart 12274)
After a relaxing, cool, fall evening in Havre de Grace, set your sights next for the picturesque Sassafras River, situated southeast of Havre de Grace and about a 15-nautical-mile journey. Again, keep clear of APG’s restricted area. About eight nautical miles upriver on the Sassafras is the pot of gold at the end of the rainbow at Georgetown, a great destination to lie back and unwind in a quiet, unhurried location.
Navigation is easy. If anchoring out is your thing, there are several great small creeks where you can drop the hook for the night. On the south side of the Sassafras, Lloyd Creek comes up first from the west, but only has one- to two-foot depths—not suitable for anchoring. Next heading east is Turner Creek, which has a somewhat tricky entrance, but has a nice nine- to 11-foot sliver where you can drop anchor.
Freeman, Island, and Woodland Creeks (which share a common entrance) have some areas in four- to five-foot depths where you can anchor, but they are open to the north and also exposed to wakes from passing river traffic. You can also anchor away from the designated mooring areas in Georgetown-proper in 16- to 20-foot depths or head up under the bascule bridge (five-foot vertical closed clearance) to some other great anchoring spots. Georgetown lies on the southern shore and Fredericktown on the northern, but most boaters consider it all part of Georgetown.
Transient marinas line both sides and many welcome transient guests. Call ahead, check their transient guests policies (they change), and secure a slip reservation. If you’re hungry, try The Granary Restaurant & Sassafras Grill at 100 George Street on the north end of the river, sandwiched between Sailing Associates and Duffy Creek Marinas. The restaurant is accented by a marina with slips for transient guests and is the sister facility to the large, well-equipped Georgetown Yacht Basin just across the river to the south. Skipjack Yachting Resort offers another marina option just west of Duffy Creek Marina. All the facilities in town are top-rate. Savor the peaceful solitude of this place. If you have a dinghy or tender with an outboard, the river above the drawbridge begs exploration, especially during the colorful autumn months.
Rockin’ Rock Hall (NOAA Charts 12274 and 12278)
Day three—you should be fully checked out from reality at this point. If not, Rock Hall is a great place to tie up, pick crabs, stroll, take a bike ride, and soak in the laid-back lifestyle of a popular Eastern Shore cruising destination. Known for its active working watermen population, the town is also a highly seasonal tourist town. Philadelphia boaters flock here to escape the city.
Heading south from the Sassafras River, pick up the well-marked Bay channel (or stay just outside to give shipping traffic room) and motor about 20 nautical miles south. Along the way, quick-flashing red buoy “38A” marks an area of eight-foot depths northwest of Worton Point; pass between this buoy and flashing red buoy “40” for the best water. As you approach Rock Hall, you might be tempted to head straight over Swan Point Bar toward Rock Hall Harbor or Swan Creek (many powerboats do). You may also head a bit farther south to green can buoy “3,” and then turn north toward town.
Rock Hall’s water scene consists of Swan Creek to the north and Rock Hall Harbor to the south. Swan Creek is the quieter, more naturally scenic side of town, while Rock Hall Harbor is where much of the “hustle and bustle” occurs. Both routes are well-marked, but the mistake boaters most often make is trying to cut straight across Rock Hall Harbor, which shoals up in the middle.
Find transient marinas on both bodies of water and again, secure reservations for this popular place first. The limited anchorage on Swan Creek fills up quickly on weekends. Shopping choices centered on Main Street run the gamut from eclectic art shops to higher-end clothing and casual wear. Rent bikes at Rock Hall Landing Marina and Swan Haven Boat Rentals. Enjoy the public beach at Ferry Park on the west side of town with great Bay views. Find the Waterman’s Museum near Haven Harbor Marina.
If you are lucky enough to make it to Rock Hall Main Street on a concert night, beat feet to The Mainstay, the town’s best kept secret, a 120-seat concert room where you will find jazz, blues, folk, and country music and other cultural activities. If you want high quality entertainment in a low-key, living-room-like setting, this is your place. If you like to pick crabs, have a casual waterfront seafood dinner, or stick around for when the band rocks the house later, try Waterman’s Crab House. The Harbor Shack (20895 Bayside Ave.), with live music, bar fare, and great people watching also sits on the harbor. Other fine eaters include Bay Wolf (21270 Rock Hall Ave.) and The Kitchen at Rock Hall (5757 Main St.). Durding’s Store (5742 Main St.) is the place to head for ice cream after dinner, and your morning caffeine infusion should come from Java Rock (21309 Sharp St.).
Bustling Baltimore (NOAA Chart 12278)
Charm City. Despite its frenetic harbor, busy shoreside pace, and heavy commercial shipping traffic, Baltimore is a great place to stay. From Rock Hall, Baltimore appears almost as a straight shot across the Bay. Not so fast, though. Remember the Swan Point Bar? Its four-foot depths seem like plenty for most power craft, but the bar is ever-changing. Green can buoy “3” marks very bottom extent of the shoal and is where you can safely point west-northwest toward Brewerton or Craighill Channel and make the approach into the Patapsco River.
At Fort McHenry, take the right branch, ending at the Inner Harbor. The city’s public docking on the west side has fixed piers, and although there are some anchoring options near the World Trade Center, we understand they crowd quickly; find better anchorages in Canton. If you’re feeling overwhelmed with choices, remember that the Inner Harbor extends seven and a half miles of walkable waterfront from the south shore to Canton. And when you tire of walking, it’s easy to find a cab or water taxi.
Ask yourself what you would like to do in the city and decide from there—of course, making slip reservations in advance whenever possible. Among our picks for Baltimore fun: visit Fort McHenry, go to an Orioles game, check out the National Aquarium, and take the kids to the Port Discovery Kids Museum. Our favorite restaurant? The Thames Street Oyster House (1278 Thames Street) in Fells Point. It’s affordable with Monday through Friday Local Happy Hour (Natty Boh oyster shooters, hon) and in a neighborhood we like to meander. For shopping, check out Zelda Zen for unique gifts and The Sound Garden for great new and used music.
