Trail News

Paddle Around America’s Birthplace in Jamestown, Virginia

bow of a kayak in the foreground with large, 17th century replica ships in the background
September 27, 2021

It’s a 10-mile journey to paddle all the way around Jamestown Island, located on the James River near Williamsburg.  Known to some as the birthplace of America, this historic island can be explored by land or water, and marks the location of the first permanent English settlement in America, dating back to 1607.

signs explaining where to launch paddle craft at Jamestown Beach park

Begin your journey at either the James City County Marina, or Jamestown Beach Event Park.  At the time of this writing (September 2021), the marina was closed for construction, but Jamestown Beach offered a suitable alternative spot to launch.  This park has a nice area for unloading kayaks and paddleboards, and a separate location for parking, which was a short walk up the hill from the beach.  The park also has restrooms!

ferry boat in the distance on the James river, water slightly choppyWhile the river may appear to be very calm at the beach, don’t be fooled.  This 10-mile journey should only be attempted by advanced paddlers.  Boat traffic, wind, and tidal currents all mixing with the flow of the river can make for an unexpectedly challenging experience.  The first challenge is navigating underneath the pier for the Jamestown-Scotland ferry.  At high tide, it might be impossible to fit under it, so be sure to check a tide chart as you are planning your trip.

pier to the ferry with the ferry boat docked in the distance; calm waters and blue skies

informational wayside about what the isthmus isShortly after passing the pier, you’ll encounter the biggest challenge of all – that little inlet under the bridge leading to Jamestown Island.  This spot is known as the isthmus, as it was just a natural, sandy strip of land that connected Jamestown Island to the mainland, but was washed away sometime during the 18th century.  Depending on the tide, the wind, and the lunar cycle, the current running under that little bridge is extremely tough to predict.  Even 200 yards out into the river you can still feel the effect of this funny little waterway, with swirling eddies and some chop, even on the calmest of days.  If you can handle paddling through the old isthmus, you can likely handle the rest of the way around the island.


stern of a kayak as it moves through a marsh creek with marsh grasses to the left and trees to the right, big blue sky tooThe creek behind the island is stunning.  Despite the sounds of boats on the river and cars on a distant highway, signs of civilization are few and far between for a mile or two.  From the lush marsh grasses to the impressive bald cypress trees and bald eagles soaring above, you can really get a sense of what the land looked and felt like when this area was first settled in the early 17th century.  But despite how peaceful the creek may seem, “peaceful” and “lush” would be a poor choice of words to describe the lives of those that settled here in 1607.  Disease, lack of freshwater, and clashes with the native Powhatan nation made for a gruesome story, which is interpreted well at Historic Jamestowne and Jamestown Settlement (more on those below).

And that peaceful feeling may not last for paddlers on this water trail.  When paddling around an island, it’s important to note that no matter what direction the wind is coming from, it’s going to be against you at some point during your trip – another reason this trail should only be paddled by advanced paddlers.  Be prepared for exposure to wind and chop, particularly on the east and south sides of the island, as those are the most exposed sections of the loop.

If the wind is not howling out of the south, several of the historic structures on Jamestown Island will be easily visible from the water, along with a few monuments.  While seeing these up close on land is pretty inspiring, viewing them from the water adds a whole new perspective.  Also, since this is a popular tourist attraction, it is highly likely that you’ll have some curious people touring the island and peering down at you!  Just smile and wave 🙂

two historic jamestown monuments viewed from the water

As you continue back to the launch at Jamestown Beach, be sure to check out the ships at Jamestown Settlement before you paddle back underneath the ferry pier.  The replicas of the Susan Constant, Godspeed, and Discovery are impressive and rare sights to see from a kayak!

Once you’ve returned back to the beach and retrieved your car, it’s definitely worth exploring Jamestown Island’s history by land.  It’s important to note that there are actually two museums here.  Historic Jamestowne is located on the island itself and does a nice job interpreting the history of the settlement, including the stories of John Smith and Pocohontas.  The other museum, Jamestown Settlement, is more of a living history, hands-on experience, depicting all aspects of Jamestown Island, from Powhatan culture to a recreated James Fort.

Happy Water Trails!

About the Author: Laura Scharle lives on the Eastern shore of Maryland and is a frequent paddler in coastal Virginia. She is a Virginia certified ecotour guide and is an independent marketing contractor with a focus in ecotourism and heritage tourism. Laura can be reached through our Eastern Shore ecotour guide listings.