Virginia's National Historic Trail Boasts Miles Of Scenery Along The Chesapeake Bay Coast

Stretching over 3,000 miles through the tidal waterways of the Chesapeake Bay, the Captain John Smith National Historic Trail is as visually stunning as it is historically rich. Those who explore it are traversing the same routes John Smith mapped between 1607 and 1609. It's the first water-based national historic trail in the United States, winding through five states and the District of Columbia, offering a blend of coastal beauty and early American heritage. Of the prettiest places to paddle in America, this is one of the best on the East Coast.

The Chesapeake Bay serves as the trail's backbone, framed by lush shorelines, salt marshes, and tidal rivers teeming with wildlife. While it's probably impossible to see it all in one go, even a short paddling or boat trip reveals expansive skies, serene waters, and a strong sense of place rooted in centuries of exploration and cultural exchange. Whether you're launching a kayak or cruising on a sailboat, the trail offers countless opportunities to engage with the landscape.

If you're flying in, Baltimore-Washington International Airport (BWI) is your best bet. From there, it's a two-hour drive south to Point Lookout State Park, one of the trail's most accessible and striking entry points. Think: rugged shoreline, Civil War history, and kayaks launching into open bay water under a pastel sky. This is where your Chesapeake journey can begin.

One of the best things about the Captain John Smith National Historic Trail is how seamlessly it blends history and nature. You're not just kayaking on a quiet river — you're tracing centuries-old exploration routes, gliding past marshes where bald eagles perch, and pulling into landing spots once used by Smith and the Powhatan people. The trail isn't linear, so there's a freedom in how you explore it. The journey can be whatever you make it to be. Start on Virginia's James River, paddle a loop off Maryland's Patuxent, or cruise along Pennsylvania's Susquehanna — each offers a different chapter of the Chesapeake's story. For planning, you can download the interactive trail brochure from the National Park Service. It includes a map, historical context, and additional resources you may find useful.

One place you should absolutely add to your itinerary is Historic Jamestowne in Virginia, where John Smith first encountered the Powhatan Confederacy. Part of Virginia's Historic Triangle, this archaeological site offers guided tours, exhibits, and a powerful look at early colonial life. The site is open daily from 9 a.m. to 5 p.m., and general admission is $15 for adults. Pro tip: Go early to beat the tour buses and catch the morning light on the James River. Bring hiking shoes, sunscreen, a camera, and binoculars. The birdwatching here is incredible, and chances are high you'll spot mocking birds, eagles, or osprey soaring overhead.

The beauty of the Captain John Smith Trail is that it meets you where you are — whether you're chasing solitude, history, or simply the salt air. Base yourself in Annapolis, Maryland for charm and walkability, or in Richmond, Virginia for arts, incredible restaurants, and easy access to several trail segments. Both cities are within a few hours of major airports, and both offer a range of stays — from boutique hotels with river views to cozy bed and breakfasts in restored colonial homes. Expect to spend $120 to $250 a night in either city, depending on the season. Summer brings warmer waters for paddling, but also crowds and humidity. Spring and fall are the best times to explore the trail, but be prepared for cooler water and changing weather patterns. For a quieter experience, aim for late September or early May when the air is crisp, the leaves are turning, and the waterways feel like your own.

If you don't have your own kayak, outfitters like Bay Venture Outfitters in Maryland  offer rentals and guided eco-tours. For something truly special, book a full-day paddle from Burnham Guides Paddling Adventures with camping along the shoreline. Waking up to a misty bay and the singing of birds is the kind of reset you can't get in the city. That's the real gift of this trail: It invites you to unplug, float, and come away with a deeper sense of the land — and possibly even yourself. Want to have a water-based adventure in the west? The Colorado River is considered the best U.S. destination for an epic kayak adventure.