Chesapeake

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Photo by: George Sass Sr.

Accessible only by boat and seven miles to the west of Crisfield across Tangier Sound is Smith Island, a window into the bay’s treasured past. Fighting a battle of erosion and disappearing wetlands, the 300 or so inhabitants continue to make a living from harvesting crabs and, to a lesser extent, welcoming adventurous tourists. Transient dock space and overnight accommodations are limited, so one of the best ways to visit is to take a day excursion boat from Crisfield. Enjoy a walk along the quaint, narrow streets and you’ll see far more crab pots than people. While you’re on the island, try a slice of the famous Smith Island Cake, featuring a dozen thin layers of cream and crushed candy bars. It was recently designated the official dessert of Maryland.

Most waterfront towns along the bay offer all kinds of maritime services, but one town stands out as especially boatcentric— Deltaville, Virginia, straddling the Rappahannock and Piankatank rivers on the lower western shore. With fewer than 1,000 residents, but more than 3,000 boats and nearly a dozen boatyards and marinas, Deltaville is a popular destination for winter storage and top-notch service work. Fall oyster roasts, art and seafood festivals, Halloween parties, farmers’ markets and Christmas cruises are reasons to visit after the summer rush.|

Deltaville

At some point during the fall one must decide whether to winter on the bay or head to the Intracoastal Waterway (ICW) in Norfolk for the 1,000-mile journey south. Even if you’re not traveling down the ICW, a cruise to the Norfolk and Portsmouth area has many rewards. Get a slip at Waterside Marina on the Norfolk side of the Elizabeth River and visit Nauticus, one of the most fascinating and educational museums in the country. Besides the fun exhibits and activities in the museum itself, you can tour the battleship USS Wisconsin, berthed next door.

Across the river is Portsmouth, which is enjoying a revival of its waterfront. Tidewater Yacht Marina and Ocean Marine Yacht Center are good places to stay, because they are within walking distance of Portsmouth’s restaurants, shops and museums. A ferry runs between Portsmouth and Waterside Park, so even if you stay on the west side of the river, you can easily visit Nauticus.

Norfolk/Portsmouth is mile zero of the Atlantic Intracoastal Waterway and 1,000 miles from the warm, sunny beaches of Florida. From here you can take the Virginia Cut or Dismal Swamp routes south. But before you head south for the winter, plan to spend the fall season exploring the magnificent Chesapeake Bay. The scenery is spectacular, wildlife is everywhere, and when you tire of secluded, empty anchorages, get a slip in a downtown marina and take advantage of what the bay’s exciting waterfront cities have to offer.