Backyard Bliss

A seasoned yachtsman recalls the magic of fall cruising on the Chesapeake Bay.

Chesapeake Bay

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.

Cruising up the Chester is doubly rewarding, its scenic shores leading to historic Chestertown, waiting to charm and entertain you. The river’s stiff current and funky bottom here can cause a restless night on the hook, so I normally get a slip at the Chestertown Marina. Homes and commercial buildings dating back to the 1700s and the nearby campus of Washington College, founded by George Washington, are beautifully restored. The better restaurants are just a block or two beyond the waterfront.

Beyond the colonial scene of Chestertown, the waterman’s town of Rock Hall is just north of the mouth of the Chester River. I prefer dropping the hook in nearby Swan Creek or getting a slip at the very attractive Haven Harbour Marina and then walking into the sleepy town of Rock Hall. On summer weekends it’s not easy getting a table at the popular Waterman’s Crab House, but during early fall, you can relax and enjoy an unobstructed view of the harbor while you feast on some of the bay’s best blue crabs.


Looking across the bay from Rock Hall, the cityscape of Baltimore is visible on a clear, fall day, and a visit to Baltimore Harbor will provide a complete change of pace. If you’re a baseball fan, the Orioles play about 10 September games at the beautiful Camden Yards ballpark, within walking distance of the downtown marinas. Baltimore’s National Aquarium offers a fascinating and forever new look at what’s under water. Nearby is Harbor Place, featuring restaurants and shops where you can get an early start on your holiday shopping. A few city blocks away, Little Italy boasts some of the best Italian restaurants on the East Coast.

For small-town charm, nothing beats St. Michaels on Maryland’s eastern shore. My family and I have been coming here for 25 years, and we still find something new every visit. Last year we arrived in time for the Halloween parade, which reminded us of why we love small towns. Local organizations, clubs, politicians and characters all played a part. One year we arrived during December’s Midnight Madness weekend, and we did all our Christmas shopping on Talbot Street, saving us the trauma of having to drive to a mall.

We try to combine an overnight trip up the nearby Wye River with our St. Michaels visits, and during the fall the scenic beauty of the Wye is priceless. Halfway up the East Wye is Dividing Creek, a popular anchorage that’s easy to enter and known for its peaceful setting. A kayak or dinghy ride along its shores will be rewarded with sights of ospreys, herons, ducks and geese — maybe an eagle — and you’ll likely see whitetail deer during a hike along the island’s six miles of trails.


Look for the second part of my article, on cruising special parts of the lower Chesapeake Bay, in the Cruising Yachtsman section of Yachting’s October issue.