Four Days Cruising the Chesapeake Bay North From the South River

Four days cruising my sailboat in the Northern Bay

Last November I had the pleasure of four days of cruising in the Northern Bay aboard Hot Pepper , my J/120 cruiser/racer, along with three crew. Here’s a brief overview of our trip.

Bay Bridge view while cruising
The author and crew began by cruising north through the center span of the Bay Bridge just as the sun began to set.

Day 1—cruising from the South River to Eagle Cove on the Magothy River

Since the South River is our home port, this is where we began our journey. But if you hail from Annapolis or the West River, you could just as easily start from there. We sailed up through the center span of the Bay Bridge just as the sun began to set and turned into the Magothy River as night fell. The last 45 minutes of our journey that day were in darkness, but the day marker beacons helped us around the northern tip of Gibson Island, where we anchored in Eagle Cove. This is quite possibly my favorite anchorage, as it’s completely protected in every direction, and the sunrise is spectacular. Plan to prepare dinner and breakfast aboard.

fun in the galley while sailboat cruising
When cruising, cooking in the galley is part of the fun.

Day 2—cruising from Eagle Cove to Georgetown, MD, on the Sassafras

This leg takes on several characteristics throughout the day. First, leaving the Magothy to head northeast across the Bay, you’ll likely spot the Francis Scott Key Bridge as you pass the mouth of the Patapsco River with the Baltimore skyline in the background. Keep an eye out for big ships entering and leaving the Patapsco. Some may be using the southern route through the Bay Bridge, while others may be using the northern channel up through the Chesapeake and Delaware Canal. It’s also interesting to line up with the signal lights designed to help guide ships on their way via either route.

As you get closer to the Eastern Shore heading up the Bay, you’ll notice the water towers of Rock Hall to your starboard. Shortly after, the Bay narrows considerably from about 10 nautical miles at Rock Hall to just five nm as you pass Hart Miller Island to port. Continuing up the Bay you’ll pass Still Pond Bay to starboard, home to Echo Hill youth summer camp, and YMCA Camp Tockwogh where I taught laser dinghy racing for two summers while I was in college in the late 1980s.

At the northern tip of Still Pond Bay is Howell Point, which also marks the mouth of the Sassafras River. The shipping channel comes within a quarter mile of the point, so keep your eye on the horizon ahead as well as astern as you approach. Rounding Howell Point to starboard, you’ll see Betterton Beach, which was once a bustling resort destination in the late 1800s and remains today a place where families can enjoy great views of the Bay and passing commercial ships.

As you sail the 12-nm distance up the Sassafras, you’ll enjoy great views of both shorelines as the river itself narrows to less than a half a mile wide just three miles upriver. Channel markers will guide you around Ordinary Point, which juts out from the northern shore. Pay close attention to the channel markers just beyond the point, as they can be a bit misleading. Continue another 4.5 nm to your destination in Georgetown, MD, where you can get a transient slip at one of several marinas. Docking on the northern shore will give you walking access to Fish Whistle and the Granary restaurants.

cruising on the Chesapeake Bay
Cruising the Chesapeake Bay

Day 3—cruising from Georgetown, MD, to Rock Hall

Reversing the trip back out the Sassafras begins the journey back down the Bay. As you pass Still Pond Bay to port, you’ll notice the shores and waters of Aberdeen Proving Ground to starboard. Note that these are restricted waters used to test live ordnance, so stay closer to the Eastern Shore to avoid an unfortunate encounter with patrol vessels.

Getting into Rock Hall requires you to double-back around the southern end of Swan Point Bar. Two green ATONs provide visual guidance around the bar to head north along the Eastern Shore to the R4 channel marker for the approach to Rock Hall Harbor. Two elongated jetties protect the harbor but define a rather narrow entrance, so watch your depth and stay close to the day markers.
North Point Marina is my personal favorite transient spot, offering clean showers, refueling, a small ship’s store and a swimming pool during the season. Several restaurants are within walking distance, including Harbor Shack and Waterman’s Crab House. The walk into the town of Rock Hall is a little over a mile from the harbor.

pink sky while cruising
Cruising to a quiet anchorage? Often a sailor is rewarded with a beautiful sunrise or sunset.

Day 4—cruising from Rock Hall to South River

The final day of the itinerary brings us back out of Rock Hall, crossing the mouth of the Chester River and Love Point, which is the northern tip of Kent Island. We always sail through the center span of the Bay Bridge to ensure ample clearance aloft and below, but watch carefully for commercial traffic, heavy tidal currents, and unpredictable wind shifts as you sail through.

Alternative Northern Bay Cruising Itinerary—Middle River and Inner Harbor

If four days is longer than you can afford to spend aboard, consider an overnight cruise up the Patapsco to Baltimore’s Inner Harbor. Our favorite transient accommodations are at Harbor View Marina, offering gated security to each individual floating dock. It’s a short walk to the Inner Harbor restaurants and attractions, but far enough away to provide a buffer of security and protection from the tourist crowds.

To add a second night to a Baltimore cruise, consider adding a night at anchor in Eagle Cove on the Magothy to the south. Or if you’d like a longer sail from the Annapolis area, consider cruising up toward Back River to anchor in Hawk Cove, nestled behind Hart-Miller Island.

These itineraries are far from exhaustive explorations of the Northern Bay. If I live to be 100 years old, I still may not have explored all there is to offer north of the Bay Bridge. Later this year, I’m planning a cruise up the Chester River to Chestertown, and I’m hoping to make it up to Havre de Grace before too long. Ahhh… so much Bay; so little time. Happy cruising!

by Steven Toole

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