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.