Tricky Waters: Eastern Shore of the Chesapeake

When I was 11, my Dad, his buddies and I sailed Wind Dancer, his C&C 37, from Long Island Sound to Chesapeake Bay. It was my second offshore passage.
Author:
Updated:
Original:
oxford%20marina

Oh, the places you’ll go!”

When Dr. Seuss wrote these words, he must have had cruisers on his mind. Rare is the cruiser who doesn’t dream of sailing over the horizon, of exploring remote areas. Distance breeds confidence, confidence breeds a taste for adventure, and few vehicles are better equipped to deliver one into the heart of the unknown than a sailboat. 

In the United States and Canada alone, cruisers can find enough challenging cruising grounds to fill a lifetime—places where the scream of an eagle, the spout of an orca or the call of a lonely loon will be the soundtrack to your days afloat. These places aren’t for greenhorns; they beckon to experienced cruisers and demand preparation and judgment. And while they vary greatly in terms of latitude and remoteness, each of these destinations harbors rewards both subtle and extravagant for those bold enough to look for them. 

Read about Pacific Northwest: Vancouver Island

West Side of the Florida Keys

Mid-Atlantic Coast: Eastern Shore of the Chesapeake

When I was 11, my Dad, his buddies and I sailed Wind Dancer, his C&C 37, from Long Island Sound to Chesapeake Bay. It was my second offshore passage. My memories of Smith Island, located in Virginia on the eastern side of the lower Chesapeake, are still vivid. Here we visited a generations-old fishing community where an archaic English dialect was still actively spoken, and where time seemed to have stopped. Once you break in with the locals, we learned, you connect with some kind-hearted souls. 

 Anchorage at St. Michael's

Anchorage at St. Michael's

Like all worthy cruising grounds, the Eastern Shore is not without its challenges. “The biggest problem is finding a safe anchorage,” says Ed Gatewood, a longtime Chesapeake cruiser. “Few creeks are navigable for vessels with [more] than three feet of draft, and some that are deep enough get shallow quickly—a sailboat can’t get far enough inside for protection from wind-driven waves in the prevailing southwesterly summer winds, which means being ready to pull up anchor in the middle of the night.” Still, Gatewood says he loves cruising there using his hook and suggests that Kiptopeke Beach (20 miles from Norfolk) offers reasonable holding and protection, thanks to the scuttled concrete McCloskey ships that were installed as a breakwater in 1948. 

The Chesapeake can be thought of as three distinct areas—the lower bay, the middle bay and the upper bay. The lower bay boasts deeper soundings and access to Norfolk, Hampton and Virginia Beach, but with the aforementioned tricky anchorages. The middle bay offers a myriad of protected harbors and attractions, including Solomons, St. Michaels and Oxford. In the upper bay, Gatewood recommends Wharton Creek, Still Pond and the Sassafras River for their safe harbors and freshwater swimming, while the views from Georgetown Yacht Basin on the Sassafras are excellent.

 St. Michael's Bay

St. Michael's Bay

I have clear memories of monitoring Wind Dancer’s anchor, but a clearer memory involves watching my Dad navigate with Loran. This often necessitated posting a bowman to scan for oyster mounds and sandbars. My job was to monitor the depth sounder. While we stayed afloat, we saw other sailboats go aground. Fortunately, they de-augured themselves by using crew on the rail, coupled with some throttle work, a time-honored technique.

 According to Kirk Adams, another longtime Chesapeake cruiser, cell service is patchy throughout the eastern shore. WiFi is available at most marinas, but signals are weak, necessitating trips ashore. Adams reports that marina amenities, like showers, laundry, fuel and water, are usually excellent, but that most pump-out stations are inconveniently situated. Also, both Gatewood and Adams point to the importance of being fully provisioned, as many grocery stores on the eastern shores are a bit “lacking” in gastronomic options.

Related

Pico-Michael

Cruising: Less (LOA) is More

The breeze kicks up. The boat digs in, and I tighten my grip on the mainsheet. It’s overcast but warm. The slate-blue water around me is patterned with whitecaps. Ahead, the low, tumbling hills of Old Mission Peninsula, a 17-mile long finger of land separating the east and west ...read more

2020-06-01_13-53-06

A New Era for Sailing Program Safety

As states begin to lift restrictions on gathering and marinas open back up, many sailing programs are still wary, especially since sailors from different households will necessarily be in close quarters, whether on their boat, in a launch or at a yacht club. Most will not be ...read more

MTcyNTIwMzc1NDYzMTkyNDkw

Zipwake

Zipwake Series S, the world's first inexpensive dynamic trim-control system, incorporates a state-of-the-art family of durable, fast-acting interceptors. The system is fully automatic, and is designed to significantly enhance performance, fuel economy, comfort and safety when ...read more

CCA-story-2048x

Safety Culture Starts with the Skipper

Sailing might not be the first pastime that comes to mind when you think of extreme sports, but that’s not to say risks don’t abound. The Cruising Club of America tackles many of them head-on in their newly released guide for skippers, Creating a Culture of Safety: The Skipper’s ...read more

GMR19_F53_0539

Boat Review: Beneteau First Yacht 53

Luxury performance-cruising isn’t entirely new. You can go fast and still be comfortable. You can even race if you make the right tradeoffs—or so says Beneteau, which recently launched its First Yacht 53, in the process also reinventing the company’s “First” brand. Design & ...read more

BirdonBoard

Cruising: Birds of a Feather

One of the neatest things about sailing offshore is the other lifeforms we encounter. We smile when we see flying fish skimming over the surface of the sea. We cheer when dolphins leap and dance in our bow waves. We are duly reverent when mighty whales sound and spout, and ...read more

pirate-marlin-logo

Pirate’s Cove Billfish Tournament

This Spring has felt a bit like a slow day of fishing but it’s almost time to time to Bait…and Switch. The Pirate’s Cove Billfish Tournaments offer something for every member of your crew. Exceptional fishing, fun times with family, old friends and new. Our run is short, our ...read more