Chesapeake Bay

Enlarge Photo

Photo by: George Sass Sr.

Years ago I was on my Grand Banks tied up at the town pier in Edgartown on Martha’s Vineyard — at the time one of my favorite cruising destinations — and an old salt on a beautiful wooden sailboat saw our Annapolis hailing port and called over, “I used to live down there on the Chesapeake, and I still miss it. There’s no better cruising on the entire East Coast.”

Well, now that I have become an old salt myself and fortunate enough to have cruised just about everywhere in North America and places beyond, I agree with him. As the largest estuary in the United States with an area of 4,500 square miles and a shoreline of nearly 12,000 miles, counting its major tributaries, the Chesapeake Bay offers virtually unlimited cruising opportunities. And in my opinion the fall season is the best time for a Chesapeake cruise. The hot, humid weather is over; the marinas, anchorages and restaurants are not crowded; the sea nettles are gone; the geese are honking, and the foliage is spectacular. Before you put your boat away for the season, consider a fall cruise to one or more of these treasured Chesapeake Bay destinations. For now, let’s explore the middle and upper bay, and in next month’s issue we’ll discover the lower bay (view the complete photo gallery here).

One of my favorite cruising spots is, of course, my hometown of Annapolis. Founded in 1694, Annapolis was a major colonial port, and today it is a thriving center for state government, tourism and maritime activities. A large mooring field is just off the city’s public docks within view of the U.S. Naval Academy, and additional moorings can be found beyond the Spa Creek Bridge. A city pump-out boat, which operates until Nov. 15, and convenient dinghy docks located throughout the downtown area make visiting boaters feel welcome. The restaurants, shops, galleries, museums, boatyards and chandleries are generally less crowded in the fall, and topping off the fall season are the United States Powerboat Show and the United States Sailboat Show, held in early October. 

A few miles northeast of Annapolis the long, deep Chester River begins a 30-mile stretch of beautiful coves, creeks and tributaries before reaching historic Chestertown. Recently, I rediscovered Queenstown Creek, seven miles from the Chester’s mouth, and after threading my way through the narrow, shallow entrance, I found a perfect spot to drop anchor off a sandy beach that projected out from the wooded shoreline. A dinghy ride to a public landing and a one-mile walk will bring you to a huge outlet shopping center, if you’re so inclined.