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The very best way to experience the Captain John Smith Chesapeake National Historic Trail is by water.

Long before Captain John Smith’s explorations of the Chesapeake and its tributaries, Indians used these waterways for fishing and hunting, to trade goods, and to explore new lands. Smith traveled nearly 3,000 miles on the Bay and its rivers, recording and mapping what he saw. Due largely to Smith’s descriptions, European settlement followed along these waterways. Traveling these waters today, you can see how the landscape has changed—and where it has changed very little; you can see where history was made and where wildlife and indigenous plants still thrive.

Here are two great ways to explore the Chesapeake’s waterways by boat:

Whatever type vessel you use, get out and experience the Chesapeake’s waterways and imagine life here before the advent of roads and bridges.

Official Boaters Guide to the Captain John Smith Chesapeake National Historic Trail

Now you can explore the Chesapeake Bay as Captain John Smith did it—by boat. But you’ll have the advantage of an expert guide who has “hindsight.” Let John Page Williams take you on a journey along the waterways traveled by Smith and discover the special places Smith described and how remarkably the same—or different—these places are today.

A Boater’s Guide to the Captain John Smith Chesapeake National Historic Trail is for boaters of all types of vessels and all skill levels. Whether you paddle, sail, or motor, whether you are a novice or a veteran boater, you’ll find the information you need to follow in Smith’s wake along the main stem of the Bay and all the rivers he traveled.

Even non-boaters will enjoy John Page Williams’s engaging way of weaving history, geography, and practical information for seeing the Chesapeake Bay in a new way. The Boater’s Guide is also loaded with links to take you to trail access points and resources where you can learn even more.

A Boater’s Guide to the Captain John Smith Chesapeake National Historic Trail is a joint project of the National Park Service, the Chesapeake Conservancy, and the Chesapeake Bay Foundation. In this first guide to America’s first national water trail, Chesapeake expert John Page Williams suggests itineraries for each area explored by Smith and tells what you need to know for exploring the areas today.

The Boater’s Guide is intended for online viewing and downloading. Download the entire document to enjoy all the interactive features designed to help you navigate quickly to specific areas of the Guide. Or download and print individual river sections to take along as you travel the trail.

This online publication will be revised periodically as new access points are developed for the Smith trail. Please contact us if you have suggestions for future editions.

Choptank and Tuckahoe Rivers Water Trail

Choptank and Tuckahoe Rivers Water Trail

This expansive water trail network on Maryland’s Eastern Shore offers 80 miles along the Choptank and Tuckahoe rivers.

Although Smith did not explore these rivers (the present-day James Islands, then connected to the mainland, obstructed his view of the wide mouth of the Choptank), he shows the area’s wooded interior on his 1612 map. His description was apt, as the Choptank Valley area was heavily forested by oaks, hickories, and chestnuts. A mature forest can still be seen today at the Adkins Arboretum near Tuckahoe State Park.

Download a pdf of the water trail map.

Elizabeth River Water Trail, Eastern Branch

This scenic Eastern Branch of the Elizabeth River provides a glimpse of the environment as Captain John Smith would have seen it. The forested shorelines and wetlands along this short paddling trail offer refuge from the urban development on other parts of the busy river.

Near the end of Smith’s second voyage on the Chesapeake in 1608, Smith sailed up the Elizabeth River, to the home of the Chisapeack (Chesapeake) Indians. He reports seeing garden plots and a few houses and “shores overgrown with the greatest pine and fir trees we ever saw in the country.”

James River Water Trails

James River Water Trail

The James River is Virginia’s largest tributary to the Chesapeake Bay and is the heartland for exploring the stories and landscapes of the Captain John Smith Chesapeake National Historic Trail. You can follow John Smith’s Adventures on the James River in series of loop trails to be explored either by car or by water.

The auto tour circles the river on both sides along scenic byways and the Colonial Parkway. The boating tour follows three loops:

  • Upper Oxbow Loop: From present-day Richmond, where the Falls of the James stopped John Smith’s river navigation, to where the river widens near Hopewell, this loop follows scenic oxbow bends along forest and marshy shorelines.
  • Cypress Loop: From Hopewell to Jamestown, this loop is characterized by stands of cypress trees and by wide marshes where the Appomattox and the Chickahominy tributaries meet the James. Historic plantations, a wildlife refuge, and popular sportfishing areas attract boaters to this scenic stretch.
  • Oyster Loop: From the historic site of the first permanent English settlement at Jamestown to the developed waterfront of Newport News, this loop offers a wide variety of water recreation. The marshes and nature preserves along the southern shore of the James River still provide visitors a glimpse of the Chesapeake in the early 17th century. But the giant oyster reefs rising from the tidal waters at the time of Captain John Smith’s explorations have vanished.

In addition to the loop trails representing John Smith’s Adventures on the James, water trail maps and guides for boating on the James are available from the James River Association. The Lower Section covers about 110 miles from Richmond to the Chesapeake Bay, an area explored thoroughly by Captain John Smith and home to the Powhatan Indians. The Middle Section covers the James between Lynchburg and Richmond, an area where Monacan Indians thrived until the mid-1700s when European settlers pushed them westward.

Mathews Blueways Water Trails

Located on the western shore of the Chesapeake Bay, the Mathews Blueways is an interconnected system of five separate water trails spanning Mathews County, Virginia. The 90 miles of trails are particularly suited for small hand-powered craft, such as canoes and touring kayaks.

Captain Smith’s shallop traveled southward along the coast of Mathews County on the night of July 18, 1608, staying close to the shore to avoid the rough waters of the open Bay. Smith was injured. The previous day a cownose ray speared his wrist at the place Smith named Stingray Point (near Deltaville, Virginia). A few days later the shallop arrived in Jamestown, ending its first voyage of the Chesapeake, but Smith returned in August to explore the Piankatank and other rivers he had missed.

Mattaponi and Pamunkey Rivers Water Trail

This water trail features the Mattaponi and Pamunkey rivers which flow into the tidal York River for a combined 120 miles. The meanderings of the two branches and the wide, deep course of the York offer a diverse landscape rich in Native American and colonial history and natural beauty for paddlers and (on the York) other boaters.

The York, Mattaponi, and Pamunkey watersheds were heavily populated by Native Americans when the English arrived. Powhatan first met Captain John Smith at Werowocomoco, the Powhatan capital, located on the north bank of the York River, near present-day Purtan Bay, Virginia. Smith showed the three rivers on his 1612 map as the Pamaunk Flu. You can follow Smith’s adventures on the Pamanunk Flu by water or land.

Monocacy River Water Trail

Monocacy River Water TrailThe Monocacy is a Maryland scenic river enjoyed by canoeists, kayakers, and fishermen. Native Americans inhabited the shores of the Monocacy for thousands of years before European settlement. Natives lived in intermittent or permanent villages, fishing and hunting as well as tilling the soil and raising corn. The Massawomeck, enemies of many of the tribes encountered by Captain John Smith, used the Monocacy River for travel into rival territories.

The Algonquian-speaking Shawnee called the river the Monnockkesy, the “river with many bends.” The Monocacy was also called “the garden creek,” for the lush vegetation bordering its banks. Both descriptions apply to the 41-mile Monocacy River Water Trail, which features rolling farmland with rock outcroppings, historic landscapes and bridges, and overhanging shade trees. Today’s paddlers can see a diversity of wildlife along the river, thanks in part, to local river conservation efforts.

Download a pdf of the water trail map.

Nanticoke River Water Trail

Stretching 63 miles from its headwaters in Delaware south to Tangier Sound in Dorchester County, Maryland, the Nanticoke River meanders through the tidal marshes, farmlands, and forests of the Chesapeake’s Eastern Shore. Much of this rural, natural landscape remains characteristic of what Captain John Smith would have seen during his explorations of the river in 1608.

Captain John Smith and the shallop crew reached the point where Broad Creek meets the Nanticoke River near present-day Seaford, Delaware. He planted a cross to indicate the extent of their explorations on June 10, 1608. Native Americans fished and farmed along this river, which they called Kuskarawaok, long before the English explorers arrived. Although hostile at first, within a few days the native Nanticoke group traded with the Englishmen. Smith wrote that the native people were excellent traders who produced highly polished shell beads, called wampumpeak.

Occoquan Water Trail

Occoquan Water TrailThis 40-mile water trail winds its way through centuries of Virginia history, while offering a broad range of paddling adventures, scenic vistas, and historic landscapes. It includes areas once visited by Captain John Smith and long occupied by Native Americans. Smith and his crew passed by the mouth of the Occoquan River on their ascent and descent of the Potomac River. At Occoquan Bay the Tauxenent gave Smith and his crew a friendly welcome. The area was a known fishing ground for Native American groups; two of the native towns were named “fish—plenty of” and “fishing place.”

The Occoquan Water Trail is in two sections, separated by the Occoquan River Dam. The upper segment runs from Bull Run down to the lake formed by the dam; below the dam the trail flows past the protected marshlands of the Mason Neck Peninsula and meets the Potomac River Water Trail to continue the journey to the Chesapeake Bay. See Trail Explorations to learn what awaits your visit along the Occoquan Water Trail

Download a pdf of the water trail maps: Lower | Upper

Potomac River Water Trail

History and nature abound along the 100-mile route linking the nation’s capital to the Chesapeake Bay. Captain John Smith explored the Potomac River as far north as Great Falls in search of precious minerals. He documented the extensive presence of Native Americans. Rich marshes provided tuckahoe, fish, and other food to indigenous cultures living along the river in more than 40 settlements.

Smith spent a month exploring the tidal waters of the Potomac and becoming acquainted with the people. The forested shorelines and brackish marshes teemed with wildlife and plants. The river was a major highway of native trade, moving copper, furs, and marine shells between the Atlantic and the Great Lakes. It has continued to course through American history as a critical route for transportation, settlement, and growth of the nation. 

The Potomac is suitable for all types of boating. Today’s river explorer can still find many river and shore vistas that are essentially unchanged from the views of 400 years ago.

Download a pdf of the water trail map.

Powhatan Creek Blueway

This 23-mile tributary of the James River, near Williamsburg, Virginia, passes through an area between the York and James rivers considered one of the most environmentally and historically significant natural resources on the Virginia Peninsula. This watershed was part of the Powhatan Indian Confederacy at the time the English settled nearby Jamestown, and Powhatan Creek was a vital resource for transportation and survival.

Today’s paddlers can still see large expanses of tuckahoe, a wetland plant that was a food staple for Native Americans. The rich flora and fauna of the tidal marshes include rare plant species and habitat for bald eagles and great blue herons. The recommended paddling route is a round trip of about eight miles along Powhatan Creek. An additional eight-mile option around Jamestown Island should only be attempted by well-prepared and highly skilled paddlers.

Download a pdf of the water trail map.

Rappahannock River Water Trail

Rappahannock River Water TrailThe longest free-flowing river on the East Coast, the Rappahannock travels 184 miles from its origin in western Virginia to Stingray Point on the Chesapeake, near Deltaville. Captain John Smith journeyed up the Rappahannock in August 1608 to just below the fall line at modern-day Fredericksburg.

Going ashore where the river was no longer navigable, Smith’s expedition was cut short by an attack from Mannahoac Indians who were gathered at a large fishing camp along the river. The English captured a wounded Mannahoac named Amoroleck. From information Amoroleck provided, Smith made a map of the upper Rappahannock and Rapidan rivers depicting the approximate location of five different Indian towns.

The Rappahannock River Water Trail features areas rich in historical and natural landscapes. The initial trail includes 27 miles of the Rappahannock from Kelly’s Ford to Fredericksburg, and 13 miles along the Rapidan tributary. A tidewater portion of the trail covers 108 miles from Fredericksburg to the Chesapeake Bay and includes a series of interpretive paddling trails for scenic tributaries of the Rappahannock.

Rivanna River Water Trail

Charting a course from Charlottesville to Columbia, Virginia, the 38-mile Rivanna River Water Trail invites visitors to explore waterways long used by Siouan-speaking peoples to travel through lands that still remain heavily forested today.

Captain John Smith did not reach the Rivanna River, but he obtained information about the native inhabitants from a captured Mannahoac named Amoroleck who described how central Virginia was settled by the Monacan. Smith included five Monacan villages on his 1612 map, and his journals indicated there were many other native towns not recorded. The Monacan Confederacy occupied the area between the Blue Ridge and the Piedmont, taking advantage of the Rivanna River for food, water, and transportation. Today’s paddlers can see the river as the Monacan saw it from their dugout canoes.

Susquehanna River Water Trail (Lower Section)

From Harrisburg, PA, to Havre de Grace, MD, this 65-mile stretch of the Susquehanna River shows off the scenic beauty of the Chesapeake’s largest tributary. On August 2, 1608, Smith’s shallop traveled up the Susquehanna just north of the present-day town of Port Deposit, MD. The rocks and riffles (shallow stretches where small waves form) are today known as Smith’s Falls, where Captain John Smith planted a cross claiming the river for the English.

Smith returned to the falls three days later, where he was met by Susquehannock leaders bearing trade goods including venison, tobacco pipes, and bows and arrows. Smith and the Susquehannocks traveled to a Tockwogh town on the Sassafras River (near present-day Kentmore Park, Maryland), where the Susquehannock and English formed an alliance.

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