By Jay Lloyd

PHILADELPHIA (CBS) — Quick. Think of a single word that you would associate with the name, Captain John Smith. Now, most folks might blurt out, “Pocahontas.” She, after all was the Indian maiden who he courted and who saved him from the wrath of her father, a major chief of Chesapeake Bay native American tribes. But for a getaway guide, the word should be “explorer” – one who left us with a National Parks water trail that can be followed by boat or car. The trail covers nearly 2,000 miles of bay, rivers, harbors and creeks that Smith explored and mapped between the Virginia Capes and the Susquehanna River. So let’s set out in the wake of the Captain to visit some key locations on a venture to Maryland and Virginia.


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Credit: Jay Lloyd

Historic Yorktown isn’t far from the original Jamestown colony near the mouth of the Chesapeake where Smith began his first bay exploration voyage. If traveling by boat simply steer up the scenic York River to the Yorktown riverfront and its restaurants, Riverwalk promenade and a beach. If you arrive by car and want to see the route to Yorktown as Smith did, take a 2 hour schooner cruise on the river with alliance Yorktown Sailing Charters. After the cruise make a lunch or dinner stop at the locally flavored Yorktown Pub or the upscale Riverwalk Restaurant. Both are heavy on seafood and signature Chesapeake catches.



Credit: Jay Lloyd

In its heyday, Cape Charles was the hub of travel between the eastern shore of the bay and Norfolk, Williamsburg and points south. It was the terminal of the Kiptopeke Ferry. That was before construction of the Bay Bridge Tunnel. Smith explored the area intensely. Today Cape Charles is enjoying a revitalization while retaining an easy-going southern pace around a harbor that welcomes cruising boats and sport fisherman and is home to a fleet of commercial fishermen, crabbers and oystermen. By auto, there’s a growing number of B&B’s and eateries. Our favorite while spending a night before crossing the bridge-tunnel is Kelly’s Gingernut Pub. It’s Irish Pub friendly, right in the heart of town and you’ll get an earful of local knowledge. The town also boasts a sizeable, clean beach.



Credit: Jay Lloyd

When Smith found his way to what today is Tilghman Island, he found a pristine setting that would be adopted by generations of Chesapeake Watermen that came in his wake seeking the bounty of the bay. Cruising in to Dogwood Harbor near the mouth of the picturesque  Choptank River and its pathway to historic Oxford and Cambridge offers a glimpse of the natural beauty of the island and a historical perspective on the life of a waterman who worked the river and bay on a classic Chesapeake Skipjack. Arrive by car and enjoy the bay views from Black Walnut Point, browse Crawford’s nautically oriented book store and then lunch at Characters Restaurant to watch the boat traffic passing through the Knapps Narrow Drawbridge. To get on the water yourself, kayak rental and fishing charters can be had across the bridge at the Knapps Narrow Marina.

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Credit: Jay Lloyd

Everything you ever wanted to know about the Chesapeake Bay – everything you wanted to experience, from recreational boating to the sight of globe girdling yachts, bay oriented restaurants, bars and favorite bay bands, are all incorporated into one town. St. Michael’s is a colorful collection of  18th and 19th century buildings set on a harbor that holds waterfront eateries, a pair of crab houses, boat rides, and welcoming marinas. The centerpiece is the dynamic Chesapeake Bay Maritime Museum,  identified by a 19th century “Cottage Lighthouse”. But if you were wondering about the boat that carried Captain John Smith on his path of exploration, a 2006 replica of his Shallop is a focal point of the museum’s floating exhibits. Twenty-eight feet long with a steerboard to maneuver while being powered by oars and sails, the replica made its own 1,750 mile Chesapeake voyage before being put on display here along with an early copy of Smith’s Map of the Virginia colony. While here, try hot, steamed crabs on the deck of the Crab Claw restaurant, drink and dance at Foxy’s, and if you don’t have your own boat take a ride on the steamer, “Patriot.”



Credit: Jay Lloyd

Stately homes line the Chester River waterfront of this 18th century town that was a major port for the shipment of tobacco when Maryland was still a colony. It was here in the Sultana BoatYard that the replica of John Smith’s Shallop was built. Tour the yard on the Chestertown waterfront and sail aboard the tall ship Sultana, which makes her homeport here. The town is a snap shot in time. It’s Victorian era Imperial Hotel and restaurant have long been magnets for travelers, seeking throwback experiences combined with flavors that span the centuries. The streets surrounding the county courthouse are lined with shops that display antique and modern Chesapeake art and artifacts. The waterfront eatery and bar, Fish Whistle is the spot to sip and sup while watching the river traffic from the outdoor deck.


These are just a few of the many sites along the unique Captain John Smith Trail that can be accessed by boat and car – some only by boat. You can get a National Park Service App with maps and information or just go online for maps, information, history and a brochure.


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