When I was a kid of about 7 along the East Coast, my uncle Sid called me up from the beach one afternoon: “Quick, Kent, run down to the inlet. There’s a sailing ship coming in and you’re not likely to ever see that again!” And there, over the rock jetty, were her old gray sails bellying out as she breasted the tide coming in, with the wind on her beam. It was, for me, the start of a lifetime’s fascination with sailing ships. And, Uncle Sid seemed to be right. The last U.S. square-rigged ship trading under sail was the Tusitala and she had made her final voyage the year before I was born.

So I was forced to read about the great sailing ships from books and later, fit two of my own boats with homemade “square” topsails to learn firsthand how these anachronisms behave at sea.

I’ve been surprised and fascinated over the intervening decades at the whole community of sail historians, worldwide, who are unwilling to see the square sail die.

Today, scores of square-rigged vessels have been resurrected or built as replicas for training ships, cruise ships or historical exercises. I have had the joy to sail on four of these: Pride of Baltimore, a 19th century replica, Providence, an 18th century replica, Godspeed and Maryland Dove, both replicas of ships from the 1600s. The progenitors of the two 17th century replicas were prime players in the European colonization of the Chesapeake. The Godspeed was one of three ships planting Jamestown and the Dove was one of two planting Maryland. The replicas are working ships as faithful to the originals as history permits.

I have been working 28 years as an ecologist to heal the wounds that we basin residents have inflicted on the Chesapeake Bay subsequent to European colonization. Although the problems we face today are of mostly our own doing, they are compounded and more complex because of mistakes made over almost four centuries. And, one must peel away layers of history to understand the Bay as it existed at the time of first contact.

Even after reading scores of early accounts of the colonial period, it is hard to place oneself in the circumstances that these early settlers faced. The ships, to my delight, have been one way to access part of this past.

Capt. Eric Speth is master of the Jamestown fleet Susan Constant, Godspeed and Discovery and Capt. Will Gates commands the Dove whose home port is historic St. Mary’s City, MD. Over the years, both have welcomed me aboard their commands to shoot color slides and video and sometimes to go aloft to experience some bit of the reality.

This autumn, I sailed with Captain Gates aboard the Dove. This is the season, in colonial times, when the tobacco fleet sailed to England, seeking to outwit unpredictable hurricanes and to beat the equinoctial and winter gales sure to follow.

Very little was more important than this trade to the colonial planters. The security of the crop and its success at market determined what goods — cloth, tools, muskets, medicinals — could return the next spring to make life easier on this difficult frontier.

Seventeenth century ships appear so unwieldy to our eyes, which are schooled to the sleek lines of modern yachts that can point up (sail close to the wind) and make swift progress within 35 degrees of the wind. The square rigger is designed to sail before the wind, with the wind abaft (behind) her beam.

Over the centuries, square-rigged ships would often anchor in the “Downs” (a safe harbor) in England, waiting weeks for a fair wind to carry them to the Azores. There, they would generally find reliable trade winds to blow them almost unceasingly across Columbus’ old route to the Caribbean. In the spring, west and southwest winds carried the mariners up to the Chesapeake.

Once in the Bay, the ships’ captains often acted as entrepreneurs — sharp and sometimes unscrupulous traders, sailing up the Bay’s tributary rivers and creeks where plantation owners would roll their tobacco, pressed densely into cylindrical casks, directly to a landing and strike their bargain.

This was the origin of the “rolling roads” found throughout the tidewater. Tobacco was best traded close to where it was cured because it “rolled poorly,” shifting and fragmenting as the casks bounced along and degrading the quality of the leaf.

Colonial administrators were frustrated by this dispersion of the trade. In the central “market townes,” of England, it was much easier to enforce policy and collect taxes! Some historians believe this convenience of a trade conduit at one’s own water gate is why the tidewaters of both Maryland and Virginia remained decentralized well into the present century.

The patience and skill of managing 17th century sailing vessels into restricted tributaries with shifting winds, oyster banks and shoals was extraordinary. There was no engine to back you off if you ran aground on a shoal without local knowledge.

Navigator Robert Tindall made a draft working chart of the lower Chesapeake in June of 1607 that shows seven shoals, apparently oyster banks, in the York River. Another version of his work, published by the Dutch several years later, maps 17 similar shoals in the James River. Any one of these could interrupt a passage, or in heavy weather result in the loss of a ship. How could these cumbersome vessels ever navigate such restricted waters?

Surprisingly, Dove ghosts along at a knot or two even in the faintest of breezes and, anchoring to avoid being carried back by unfavorable tides, she might even work her way 15 miles up labyrinthian creeks in a day’s time. But when the wind is in her face — blowing from the direction she wishes to go — a pinnace such as the Dove can only angle up within about 60 degrees of the wind, twisting or “bracing” the yards (crossing spars that spread her sails) as nearly parallel to the ship’s centerline as complex rigging will allow.

To tack a modern yacht with “fore and aft” sails attached directly to the mast, one simply turns into the wind. The sails “luff” (flap) until the boat has turned past the wind direction, letting the sails fill on the other side, thus zig-zagging, by stages, to windward. Aboard the square-rigged Dove we round (turned) the ship up into the wind until the big square sails are blown backward against the rigging, virtually stopping the ship’s 42 tons. The captain cries “Mainsail haul” and the yards are swung around by the crew slacking and hauling a dozen or more lines exactly in concert. The ship fills her sails with wind on the other side and crew trims (adjusts) them for best effect on the opposite tack, thus advancing slowly and with much labor, to windward.

Square-rigged ship rigs are designed to bear tremendous wind forces from behind. In heavy weather, when the ship is tacked, blowing the sails “aback” against the rigging, creates a real danger of being dismasted. So instead, she is turned downwind in a circle, continually adjusting the dozen or more lines controlling the yards first square to the centerline, then hauling them in until they are braced on the other tack.

This maneuver, while safer for the ship and her rig, meant a lot of lost ground in making perhaps a mile’s circle. Also, it couldn’t be done in close quarters without sea room.

On a modern sailing vessel to strike (lower) a sail, one lets go of the halyard (line used to raise sails) and it comes down; to set it you pull the same rope! Setting and furling sails on 17th century model ships can’t be done from the deck. Crew have to go aloft on “ratline” ladders, laced to the rigging, which sway, pitch and jerk tight with the ship’s wallowing motion. You step off —virtually into space, with the deck many yards below — and sidle out along the yardarms to port or starboard. Your feet are braced on footropes looped horizontally under the spar and your belly is bent over the wooden yard. Both hands are employed trying to loose or gather a thousand square feet of heavy canvas which billows below. No “one hand for the ship” here.

When anyone else steps onto the footropes, they have to sound off: “Laying on starboard (or port)!” or the changing weight distribution can pitch the first guy to his death on deck or into the sea. The same goes for “laying off” the footropes. In the old days, there were no safety nets and no way to stop to pick up the unfortunate, although it was likely that he couldn’t swim anyhow. For those who landed on deck and survived … well, these were the days before even rudimentary antiseptics, anesthetics and orthopedic surgeons, let alone workman’s compensation.

Getting sail in is extreme labor in heavy weather. Clew and buntlines are hauled from the deck to bunch the sails up as far as possible against the yards, but great bulges of canvas still gallop in the wind. A wet maincourse, the largest sail in these ships, could weigh hundreds of pounds, thousands of pounds in a big warship. In a blow, both hands are needed for furling, fists to pound hand-holds into drum-tight, often wet or ice-covered canvas and haul it up close to the yard. “Gasket” lines hanging from the yard are spiral-wound around the sail, containing it by stages and squeezing out the wind until it lies furled, like a tamed canvas sausage, along the spar.

Sailors throughout the history of square sail have trimmed their fingernails back to the quick. Any rim of nail showing risks being torn entirely off by rough, thrashing canvas as one struggles aloft in a storm. I know from 44 years of sailing that you might not even feel it until much later, when it starts bleeding … and hurting.

Even on the Dove, counting those on deck, a dozens pair of hands might be necessary to get in sail during heavy weather. We had 11 working crew aboard the Dove which displaces 42 tons. The Delaware River’s reconstructed Kalmar Nyckel weighs in at 350 tons. Imagine the requirements of a thousand-ton man-o’-war.

On my last trip aboard the Dove, four of us serviced the mainmast, going aloft twice to climb out, set and furl the maincourse, then hanging upside down from the futtock shrouds and swinging up into the tops, a platform where the large mainmast is joined to the smaller but still higher topmast to set and furl the topsail. Four more crew went aloft on the foremast, a total of eight aloft. It was light weather, we wore modern safety harnesses “clipped in” to the rigging and under the skilled eye of Sailing Master John Fulchiron, we dealt only with the weight of canvas, our own balance, and securing the gaskets. A proper knot can be untied quickly!

My colleagues and I often speculate what life in the 17th century Chesapeake was really like. We would dearly love to see it, see what the Bay, her great fisheries, the forests, the people were like, but were we really born too late? Would we have wanted to live then?

In the 17th century, I would have been considered an “ancient,” unsuited for such work above deck. When the Dove came into her pier at St Mary’s City, I was still aloft with crewmates passing the gaskets. It was near dark when I hiked up the steep river bank with the daylight dying behind me.

I had already had a physically demanding day before joining the Dove and was really tired. I’d cut firewood for winter, hauled one of my own, small boats up 38 feet of river bank, had been immersed in salt water part of the day and was sweaty enough to attract a cloud of mosquitoes.

I imagined I was back in time, passing the dingy unpainted clapboards of Farthing’s Ordinary in St. Mary’s City. The mosquitoes would likely have borne malaria. It was likely that I hadn’t bathed for five weeks, was probably cut and injured from some accidents of the voyage and was now bound back to some rude cabin laboriously and inexpertly built from forest products.

I was only here, after all, because of my failure to earn a living in England and had shipped out of Bristol on the southwest coast as an alternative to debtor’s prison five years ago. Starting with nothing, I had just 50 acres, a suit of rough clothes and a few tools after three years of indentured servitude under a demanding master.

Mice, insects and mold had moved in during my absence. The tobacco that was my livelihood was overgrown with weeds and much plagued with the worm. Squirrel and deer had eaten far too much of my winters corn — the food supply. The “salvage” Piscataway Indians had stolen my large iron pot. My own “indentured man,” in addition to the work left undone, had absconded, taking one of my two steel axes. My woman, herself a transport from Newgate Prison was showing symptoms in the latter-stages of French Pox. I would certainly have died within the year, and being illiterate, could not have even made a will.

Despite my eagerness about Chesapeake history, I was most grateful to get on the highway and drive 22 miles home (two day’s walk, plus a ferry in 17th century Maryland) for a good dinner, a long hot shower and the ability to stretch out with my purring cat for a quiet night on clean white sheets!