It was the ninth day of June, late spring in 1608, and the first voyage of discovery in the Chesapeake Bay was in progress. There’s evidence that it was sunny and clear because John Smith and his crew, emerging from behind islands on the Eastern Shore, could see land northwest on the horizon:

“Finding this eastern shore shallow broken isles, and for most part without fresh water; we passed by the straits of Limbo (today’s Hooper Straits) for the western shore: so broad is the bay here, we could scarce perceive the great high cliffs on the other side.”

And ever since, we have referred to the opposite sides of the Chesapeake as the Eastern and Western shores.

Those cliffs, when lit by morning sun in clear weather—bright landmarks from Hooper Straits as one emerges from behind what Smith named Momford’s Poynt—compared to the darker, tree-lined shores also visible from this location, must have beckoned the explorers irresistibly. In hot, calm weather, the cliffs assume a mirage quality, hovering disembodied above the horizon.

This spring, I sailed out of the Patuxent River in a 27-foot sloop to embark on parts of Smith’s two 1608 voyages. The Eagle, at 1.25 tons, is about a third of the weight of Smith’s discovery barge, but she’s rigged with mainsail and jib, much like what researchers suggest was used by the explorers nearly 400 years ago. Eagle’s sails fill to the rising southerly wind and I am swept along with wind and tide together; the fairest condition a sailor can ask.

The cliffs at Little Cove Point on the port side rise 131 feet, more than four times the height of Eagle’s mast. I round Cove Point where four centuries ago the flooding tide swept the voyagers north past the Patuxent River, bringing them ashore at the cliff’s highest rampart.

“By them we anchored and called them Rocky Point.”

These ramparts are gone. An estimated 300 feet of cliffs have eroded into the Bay since Smith’s voyage; a hard lesson learned by hundreds who perched their dwellings too close to the edge. In 1972, my wife, Nancy, and I were drawn to a cliff-top cottage near Chesapeake Beach, but cracks in the foundation led us to walk the beach at the foot of the cliff 100 feet below. Emerging from the crumbled soil of a recent breakdown, was a telephone.

Rocky Point itself stands about 140 feet above the Bay and a knoll slightly inland rises 160 feet. The tree line raises the profile another 50–100 feet.

The cliffs are multicolored sands and clays, but somewhat above sea level is a hard, 30-inch layer of limonite iron ore that protrudes from the cliff, resisting erosion, until it breaks and falls to the beach in great stony blocks.

The cliffs continue along nearly 30 miles, interspersed by hanging valleys with cold artesian springs and marshy intrusions with meandering freshwater streams.

Smith collectively named these features Rickards Cliffs, after his mother’s family.

“Thirty leagues we sailed more northwards.” He was again clearly profiting from the Bay’s spring southerlies, generated daily as the sun-warmed land heats and drives the air above upward, drawing air from the still-cooler Chesapeake toward the north at an accelerating rate from morning until the sun begins to sink.

The voyagers were curious about the almost mountainous aspect of this shoreline. “Leaving all the eastern shore, low islands, but overgrown with wood as all the coast behind them, so far as we could see; the western shore by which we sailed we found all along well watered, but very mountainous and barren, the valleys very fertile but extreme thick with small wood as well as trees, and much frequented with wolves, bears deer and other wild beasts. We passed many shallow creeks.”

Parkers Creek is very likely unchanged from the streams Smith and his adventurers saw in 1608. Other inlets—Flag Harbor, Plum Point, Fishing Creek, Rockhold Creek and the small rivers to the north—have all been dredged, embanked and filled with housing and marinas.

Smith, diverted by the cliffs, and no doubt urged northward by the wind, dismissed the Eastern Shore with that simple sentence. How could he have missed the Choptank and Chester rivers?

In 1608, those “low islands but overgrown with wood” were substantially larger and formed a visual screen across those river mouths.

Oceanographer Bill Cronin wrote that across the Choptank mouth alone, James Island was more than 1,300 acres and a couple of miles long. Its remnants today total just 85 acres. Eagle pulled up on the east side of James Island, a place of solitude and uninhabited wildness that I have cherished more than three decades.

This may change, though, as it is on the short list to be the next site to contain the continuing flow of dredged material from the Bay’s navigation channels. The material would be placed behind huge stone dikes that would be built along the perimeter of its 1840’s footprint. I hope I am too old and feeble to sail there when that day comes.

Nearby was Sharps Island—once 900 acres—which vanished completely in 1963.

Long after John Smith, mariners were warned off Sharps Island by a series of lighthouses, the first of which toppled from erosion.

The next, a screwpile light, was carried away by ice, along with its terrified crew. Cronin wrote that they were rescued after a harrowing ride of 16 hours borne along by the floes.

The present Sharps Island Light is a caisson, built on a 5-acre island remnant in 1882. The land has since eroded, and its footings were threatened by ice in 1973 and 1976. It cants improbably like the Leaning Tower of Pisa to this day.

Sharp’s disappearance, though, did not remove the navigation hazard of the shoal left beneath her footprint, nor the remnants of some building foundations not far below the surface.

I stayed close along the Eastern Shore islands missed by Smith. He and his adventurers went into the Patapsco River—now Baltimore—which interested him as “the first we found navigable for a ship.”

Eagle’s shoal draft allowed me to sail close to shore up the length of Tilghman Island and I thought that in 1608, this shore would have indeed looked overgrown with wood and monotonous compared to the cliffs Smith passed west of here.

Tilghman, too, is eroding at her perimeters, and where one bank has recently been riprapped, the collapsing shore has exposed the whole face of an old forest in cross section, revealing the structure of the Eastern deciduous community that enthralled early colonists: tall trees with straight trunks growing up from the dark forest floor in competition for light, then spreading a vase-shaped fan of leafy branches in an overarching canopy.

Underneath is a second canopy of near uniform height where smaller trees like dogwood and holly, which are tolerant of shade, put out their greatest energy and blossom in early spring before the canopy above closes them in shade.

Beneath these in still lower light is an herbaceous layer, where one is able to move without the impediment of invasive exotics like Japanese honeysuckle or kudzu, which so often overrun similar woodland patches today.

At the end of this eroding shore was the edge of this old woodland, where the tall, interior forest trees were canted outward toward more open ground, their branches reaching out and up for light. Other scrub and meadow species crowded into and up against the understory layer.

In 1608, this forest edge would have probably contained abundant blackberry and greenbriar to snag fur, skin and English garments.

Eagle sailed through Poplar Island Narrows, between Kent and Poplar islands, the latter eroded in past decades to remnants.

While its companion, Coaches Island, looked much as I remembered it in the early 1970s. Poplar Island now features a few miles of high stone walls marking a geometric area to the north and west, where a great cavity is quickly being filled with soupy sediment from the approach and channels of Baltimore Harbor.

Equipment breaks the crust of this soup, which, when exposed to air, slowly settles, compacts and dries, decreasing in volume, to make room for yet more mud.

Conduits continually pump or drain and discharge interstitial water from the sediment, and return it to the Bay, which contributes to its turbidity and releases nutrients once sequestered on the bottom.

In wet springs, rainfall threatens to outdo evaporation, and water accumulates over the project.

Contractors, the Maryland Port Administration and the Corps of Engineers are working to establish marsh and upland habitat around the edges of this, but storms, like Isabel in September 2003, can tear up what’s taken several seasons to grow or build.

I sailed Eagle behind Kent Island and anchored in Marshy Creek for the night.

On the starboard side are broad saltmeadows dotted with copses of trees growing on higher hummocks of land. Herons fished the margins and royal terns skirled. At day’s end, mosquitoes and minute, white, biting gnats emerged from the saltmarsh.

Smith and his mariners never mentioned these pests, and I wonder if some subtle ecological difference in the past was responsible for this silence, or were they so used to the bother of their own lice and fleas that the external annoyance was trivial?

On the port side, there was no hint of marsh, just solid bulkhead and an unbroken phalanx of condominium units. I wondered how, in these last few decades of environmental awareness, zoning had allowed such a complex to be put directly on the water. Quite a few invasive mute swans, which had not been introduced to North America until after Smith’s voyage, were cruising about.

When night fell, the insects subsided and I enjoyed moonlight over the marshes. In the other direction, only 16 of the 100 condos visible from where Eagle lay showed any sign of lights. Who owns these units and where did they really live?

The next morning echoed the 1608 mariner’s voyage: A nor’east storm was brewing off the coast.

When the expedition attempted to go up the Bay in 1608, in addition to being disheartened by the discomforts of small boat voyaging, they recorded: “two or three days we expected [experienced] wind and weather, whose adverse extremities added such discouragement, that three or four fell sick, whose pitiful complaints caused us to return, leaving the Bay some nine miles broad at nine and ten fathoms water.”

Making an attempt to beat up the Bay against that nor’east wind would logically have brought them close to the eastern side of the Bay, where the only depths of that magnitude (45-62 feet on modern charts) can be found in the Upper Chesapeake. This breadth would approximate the area between the Patapsco and the Eastern Shore near Rock Hall, where Smith would later show a tribe, the Ozinies, on his famous map.

He named the nearby land Bornes Poynt, perhaps today’s Swan Point, and his map shows an inland creek which could be Swan Creek, which is today a decent boat anchorage, with a good lee from the northeast.

Smith may have retreated, but he still had many more adventures on his first voyage as his crew regained some strength and spirit as they worked their way south.

In July, only a few days after reaching Jamestown, Smith would finish the summer exploring the Chesapeake.

Coming in September: Retracing John Smith’s return to the Upper Bay.