The Chesapeake Bay with its gentle waters, steady winds, and rich history provides some of the best sailing in the world. And two of my favorite destinations, Worton and Swan Creeks, are easily accessible to Philadelphia boaters.
Worton, a quiet haven surrounded by farmland, bald eagles, and beautiful beaches, is one of the bay's best-kept secrets. My favorite spot is a long stretch of beach just off the anchorage on the north shore that's a great place to drop a blanket, read a book, and laze away a summer afternoon. A bit farther in, there's a large sandbar that's a little more popular - you might have to share it with one or two other boats.
After watching the last of the red glow sink in the western sky over Pooles Island, you can cook up a meal in your tiny galley, or, better yet, hop in your dinghy and motor down to one of my favorite restaurants on the Bay, the Harbor House. This is not your standard Eastern Shore crab-shack fare served in those little red-and-white paper containers with plastic forks and runny coleslaw. The chef is fantastic and the wine list is spectacular. I've had many great meals at the Harbor House and they never disappoint. I recommend booking in advance; this place gets full. One of my favorite meals there was on the Fourth of July, when my guest and I had medium-rare filet mignon, a Chimney Rock cabernet, and a clear view of the fireworks bursting over Chestertown. That was a night.
If you're looking for a little more variety in your sailing adventure, Swan Creek is your spot. Swan offers the best of both worlds - a peaceful, quiet anchorage tucked into one of the Eastern Shore's most beautiful rivers, and a wide selection of dining, attractions, and activities that will fill both your day and night.
The anchorage in Swan Creek is large and rarely too crowded. However, if you want a more luxurious experience, I recommend checking out Osprey Point Marina & Inn. I first visited this historic country inn when I took my parents there for their anniversary. Osprey Point embraces the spirit and style of the Eastern Shore and serves some of the best cuisine in Rock Hall. The inn provides shuttle service to town and offers bikes, kayaks, a pool, and picnic areas with charcoal grills. A night or two off the boat is nice, especially if you have guests new to sailing. Who wouldn't trade a hunk of foam and a slight diesel smell for a large, firm mattress with crisp white sheets and a chocolate on the pillow?
Rock Hall, a short walk from Swan Creek, is a classic Eastern Shore town with picture-postcard waterfront houses, shopping, crab shacks, fine dining, and live music. During the day, wander around the waterfront and check out the boats, or stroll through town, where you'll find antiques, crafts, clothing, gifts, and jewelry. Don't leave without stopping at Durding's Store on Main Street. This circa-1925 soda fountain serves to-die-for treats, homemade baked goods, and ice cream. If you happen to visit Rock Hall on July 1, you'll witness Kent County Watermen's Day, celebrating the men and women of Rock Hall who make their living from the bay. One hallmark contest of this weekend is the Work Boat Docking Contest. Boat owners know that docking can be stressful, especially with a 20-knot cross wind. Yet these pros make it look easy. Of course, there are those who "miss the mark," which only adds to the entertainment.
For nightlife, my two favorite spots are the Harbor Shack and Waterman's Crab House. Both offer great live music and tasty food, so you can't go wrong whichever you choose. (I usually just pick the place that has the better band.) If it's your first time on the Eastern Shore, order the all-you-can-eat crabs with a bucket of Natty Boh beer. That's about as local as you can get.
Philadelphia sailors don't have far to go to experience some of the Chesapeake Bay's best destinations. Spring, summer, or fall, Worton and Swan Creeks provide a first-class experience and lasting memories. And because these spots are high up on the bay, the jellyfish rarely invade, so the swimming is good all season long.
I make a lot of trips to Worton and Swan over the summer. So if you happen to make it to one of these locations, keep an eye out for a white C & C 30 Mark II with the name "Merritt" stenciled across the back. Hope to see you out on the water.