Captain john Smith, when he could tear himself away from Pocahontas, was an obsessive explorer. Now, the National Park Services has created a “water trail” that follows his 17th-century travels up and down the nearby Chesapeake Bay. In a recent article, we pinpointed some of his southern stops that can be reached by car, boat or bike.
Now, let’s turn to his northern discoveries. -Jay Lloyd
The carefully preserved colonial village of Chestertown — located on the winding, crab-filled Chester River — is a fitting place to start. It’s here that the replica of Smith’s shallop was built to celebrate the 400th anniversary of his arrival in Jamestown. The boat, powered by sail and oars, was then used to retrace his exploration of the bay. Chestertown is rich in history, restaurants and scenic vantage points. If you arrive by car or boat, things to do include a cruise on the schooner Sultana, a replica of an 18th-century Royal Navy patrol schooner. If you have time for one meal in town, grab a riverside table at the Fish Whistle. It’s a cut above pub food with a straight-from-the-sea approach. And there’s outdoor dining with a river view and an easy breeze on a warm bay day.
EASTERN NECK NATIONAL WILDLIFE REFUGE
Where the Chester River flows into the Chesapeake Bay, the northern landfall forms the Eastern Neck Wildlife Refuge. It’s a haven for migrating water fowl and a population of soaring osprey that nest on buoys and navigation markers. It’s also a spot where the American Bald Eagle has made an amazing comeback. You can explore Eastern Neck by bicycle, hiking trails or, if you bring a trailer-able boat, by water. You’ll also find spots to drop a crab line. Nearby things to do include a visit to the town of Rock Hall (just to the north) and taking a sailing cruise on the Crab Royale (Full disclosure here: I have frequently sailed as First Mate with Royale’s skipper Cap’n Mark Einstein). On your return, step onto the deck of the Waterman’s Crab House for a dockside crab feast on Rock Hall Harbor.
ST. MICHAELS, MD
St. Michaels, a colonial trading center on the Maryland Eastern Shore, is a dynamic boating town that holds as a centerpiece the highly lauded Chesapeake Bay Maritime Museum and its collection on historic bay craft. A landmark “Screwpile Lighthouse” guards the bustling harbor. This is one of the most popular Eastern Shore destinations for a visiting international fleet of yachts. Restaurants and activities are alive here. For Chesapeake steamed crabs, head for The Crab Claw, next to the museum. Take a harbor tour on the Patriot, a colorful day cruiser that plies the harbor and Miles River coastline. For overnight stays, bed and breakfasts dot the town and there’s a full-scale resort hotel.
John Smith also extensively explored the western shore of bay and when pointing his bow into the broad Severn River, could never have imagined that one day a town set on its southern bank would symbolize the nautical past, present and future of a new country. Annapolis is a must-visit by car, but preferably by boat, where you can breeze into the harbor while gliding past the U.S. Naval Academy. You’ll find shoreside restaurants and marinas on a harbor where everything that floats –from paddle boards to world class yachts — pick their way through a mooring field of visiting vessels. Here, you should take a self-guided tour of the Naval Academy. Don’t miss the museum and a visit to the crypt of John Paul Jones. Take sailing lessons at the Annapolis Sailing School or a cruise on a Woodwind Schooner. For dinner, visit Harry Browne’s on the circle surrounding the Maryland Capitol or the Chart House in Eastport. For crabs, try Buddy’s on Main Street or take a short drive to Edgewater and Mike’s Crab House on the South River.
Off Route 2, south of Annapolis
There’s a snug destination on the West River south of Annapolis where a pair of fun restaurants cater to the “crack and pick” crowd as well as sailors who prefer to sit down with a knife and fork. Most visitors arrive here by boat to overnight at the waterfront marinas. We usually tie up at The Pirates Cove. It’s a central stop where you can park the boat and step ashore for a sit-down dinner, or if arriving by car, stay at the Cove’s cozy inn. There’s even weekend entertainment and dancing. And just two blocks away on the waterfront, you’ll find Thursdays, where crabs are always in the steamer and the beer keeps flowing. It’s a good spot to hang out and watch the parade of arriving boats.
One of the most scenic rivers on the Historic John Smith National Water Trail is the Wye. It flows into the Miles River, just north of St. Michaels. It’s a wonderful river to explore by boat or kayak, with deep water, a picturesque coastline and abundant wildlife. You can drop a crab or fishing line anywhere.
A well-protected anchorage here is also a popular weekend destination for cruising sailors. Shaw Bay, just inside the Wye River and around a bend to right, produces a good swim spot and easy paddleboarding. If you want a little more privacy, head for Lloyd Creek; just hang another right at the mouth of Shaw Bay. You might even catch your own dinner!
Note: The National Park Service offers a free smartphone app called Chesapeake Explorer that covers the John Smith Water Trail. For planning purposes at home, just go to this Park Service website.