8th Annual RMHC Telethon: More Than $1.2 Million Raised | #RMHCCBS3 | Bidding For Good | Photos 

Getaway Guide: The Captain John Smith Water Trail

June 19, 2014 7:00 AM

(credit: Jay Lloyd)

Reporting Jay Lloyd

Bet you didn’t know that June is National Trails Month. It’s the perfect time for celebrating America’s vast system of historic and recreational trails. The weather now is generally ideal for hiking, biking, horseback riding – even boating on a trail. Which brings us to the Captain John Smith National Historic trail. Yes, that John Smith, of Pocahontas fame. Parts of this trail are as close as an hour from home and can be accessed by the waters of the Chesapeake Bay. After landing at Jamestown, Smith explored the pristine waterway in a boat powered by oars and sail. He could reach into shallow creeks and explored over 3,000 miles of shoreline. Here are a few of my favorite spots to visit and explore by boat, car or bike. – Jay Lloyd



The link provides handy maps and a description of points of interest throughout Maryland and Virginia where John Smith stopped on his travels along both shores of the bay, from the historic Jamestown Colony to the Susquehanna River.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


On the western Virginia shore of the Chesapeake Bay, the James River flows to the original Jamestown colony. While visiting the restored colony is enlightening side trip during a getaway to nearby Williamsburg, exploring the James River by canoe or kayak, or hiking the shoreline gives you a unique view into what the early settlers might have experienced. Isolated beaches along the river provide picnic stops to sit and water gaze.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


Close to the storied battlefield that saw an end to the Revolutionary War, you’ll find Yorktown, an early port on the banks of the York River. If you’re without canoe or kayak, you can sign on for a two hour sailing cruise to explore the river on a pair of sleek schooners, the Alliance and Serenity that leave from the Yorktown docks. The tab for a two hour cruise is $35 for adults, $20 a child. After the sail, enjoy some time on a sandy beach with a nearby pub.

(credit: Jay Lloyd)

(credit: Jay Lloyd)



Chesapeake Bay sailors often bypass this quiet port on the eastern shore of Virginia in favor of the more lively spots around Norfolk, across the bay. They miss a rare treat in a restored 19th century town with deep water for sailboats, water sports, an expansive beach, golfing and two enjoyable restaurants that we had time to visit on a recent stop. If you’re returning home from a Williamsburg trip, don’t miss a chance to drive the 20 mile Chesapeake Bay Bridge-Tunnel. There’s a lookout rest, to stop along the span for a view of John Smith’s entry point to the new world. Then spend a night or more at Cape Charles.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


Returning home along the eastern shore of Virginia and Maryland may take a bit longer than dodging trucks up I-95, but the route is scenic and leisurely with interesting stops along the way. My favorite is Cambridge, Maryland, another point on the water trail. It was the setting for a contemporary town in James Michener’s “Chesapeake.” The crab processing plant is still there and Maryland steamed crabs are a Cambridge specialty. A Hyatt Regency resort is planted on the banks of the Choptank River where overnight guests can take a sailing cruise, play a round on a manicured golf course or just enjoy high quality dining on the waterfront. The Hyatt is popular with power boaters who dock overnight and take rooms at the hotel. Sailors note: The route 50 bridge is too low for sailboat passage to the hotel, but you can tie up at a public dock on the city side of the bridge.

That’s a lot of trail to cover in one getaway. We’ll look at more of Captain John Smith’s landfalls with a northern tilt in a separate upcoming article.

Note: The National Park Service offers a free smartphone app called “Chesapeake Explorer.” It guides you along the water trail and to other sites and activities on federal parkland along the length of the bay. It’s well worth a download for anyone who enjoys a Chesapeake Bay getaway.

More From CBS Philly

52nd ACM Awards
Getaway Guide To Senior Discounts

Listen Live