My partner Mike’s family and mine have long histories with the Chesapeake Bay. His family settled on the eastern shore in 1640, while mine must have been there as well, with ancestral names of Tilghman (Tilghman Island) and Emory (Emory Creek). We surmise we’re related.
Mike has worked, cruised, and delivered yachts on the Bay (as it’s called by locals) for much of his life, and can navigate it with his eyes closed in any kind of weather. I used to pass through quickly, sailing my Hylas between Maine or Lake Ontario and Florida with the mandatory stop in Annapolis at famed Marmaduke’s Pub in Eastport. Sadly, Duke’s (where the guy on the stool next to you may have single-handed over from Capetown) is long gone, but Annapolis is still the sailing capital of the East.
The picturesque Maryland capitol rolls out rich history, quaint shops and of course nightlife. To fully experience this historic city, pick up a city mooring ball, and watch boaters as they negotiate their way down Ego Alley. When the sun goes down, take the water taxi ashore to sample the nightlife and enjoy a Painkiller at Pusser’s. Or head to Eastport, where the real sailors go, to Davis’ Pub, The Boat Yard, or any of the other pub-style establishments.
In peak season, you don’t need a chart or a GPS to cruise between Annapolis and St. Michaels or Rock Hall. Simply follow the crowd. Both are very popular destinations; however if, like us, you wish to avoid crowds, there are many more places on the Bay to cruise.
With over 8,000 miles of shoreline, the Chesapeake Bay offers a greater variety of experiences and anchorages than you’ll find anywhere else on the eastern seaboard. From quiet gunkholing with eagles soaring above to downtown Baltimore and a night of pub crawling, the Bay has it all. After decades of cruising this great body of water we still have barely scratched the surface of all the Bay has to offer. In fact, I’m ashamed to admit it, but I’ve never been into Baltimore by boat.
Poker runs and charity sailing events fill the summer calendar. One of the best regattas to watch is the log canoe fleet racing along the Eastern Shore featuring stunning antique sailing canoes once used as oyster boats. Captain and crew choreograph their tacks, using exceptional skill and balance, to round the buoys without overturning.
At the fall Oyster Festival on Tilghman Island, present day commercial fishermen demonstrate their amazing boat handling skills as they back lengthy single engine vessels into slips in the blink of an eye. Precision and timing are required to claim bragging rights.
Cruising the Bay in the early morning mist, watching watermen tending their crab pots is one of life’s special moments. We delight in spotting a schooner, a Chesapeake Bay Skipjack or a Buyboat – these vessels are the fabric of the Chesapeake’s history. Thirty four of the original 75 lighthouses are still standing, guiding boaters away from shoals. The screw-pile desiged Thomas Point Shoal Light near Annapolis, is the most well-known in the Chesapeake.
When we’re in the Bay, our home port is the beautiful historic village of Oxford, off the Tred Avon River. Here life seems to stand still. Trees overhang the single main street and flowers are everywhere. Traffic is nonexistent. Within walking distance are excellent pubs and restaurants serving hardshell crabs, and there is a small grocery store. There are several nice marinas and a good anchorage if you’re careful to watch your depths.
When leaving Oxford, cruise the Tred Avon River right up to Easton or head out to Tilghman or up the Choptank River to Cambridge. Like the scenic Chester River to the north, this is a really nice side trip, especially when the weather is kicking up the Bay.
My favorite anchorage is a small bowl between Oxford and Cambridge on La Trappe Creek. With a marked entrance, this protected anchorage is shaped like a miniature Sandy Hook, N.J. Boaters and their pets can dinghy over to the sandbar and relax in tranquility just off the River.
We can’t forget to tell you about the James and Chickahominy Rivers at the southern end of the Bay. North of Norfolk, the James River surprised us with wave heights you’d normally not see in a semi-protected area, so we didn’t have a chance to enjoy the sandy beaches along the shoreline. This route passes some of the area’s best known historic destinations, including Jamestown. Unfortunately there is very limited dockage there except at a nearby resort. It’s well worth a stop at the junction of the two rivers where there is a very nice marina and a park.
The Chickahominy, which in Algonquin means “the course-ground stone people,” was explored by Capt. John Smith in the early 1600s, and it is said he was captured upriver on Smith Island. Lined by cypress and rich in waterfowl and fish, the river is navigable for about 17 miles, much of the course unchanged by the centuries. Cruising this surprisingly deep river you can anchor, or stop at one of the charming restaurants with marinas along the way.
We stayed a bit longer than we’d anticipated at the delightful marina/restaurant across from Smith Island, as we lost a transmission. Happily, the staff was able to replace it while we enjoyed some hospitality we’ll never forget, proving once again that some of your most memorable cruises are those when you encounter a breakdown.
These are just a few of many wonderful places to explore on the Chesapeake Bay. Take a week, a month or an entire summer for something memorable every day. And come back soon.