Captain John Smith Explores Chesapeake Bay by Sail

John Smith’s claim of being saved by Pocahontas might stretch the truth, but his exploration of Chesapeake Bay is truly legendary.

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Captain John Smith’s 1612 map of Virginia depicts Chesapeake Bay and all major tributaries with surprising accuracy. North is to the right. Courtesy Library of Congress.

In December 1606, the Virginia Company of London sent three ships across the Atlantic seeking gold, silver, and colonial advantage in the New World. Aboard one of those vessels sailed a mercenary soldier and former slave named John Smith.

During the ocean passage, Smith was accused of mutiny and sentenced to hanging. But he got a reprieve when expedition leaders unsealed official Virginia Company orders and found Smith had been appointed to the leadership council of their fledgling colony.

The explorers entered the mouth of Chesapeake Bay in April of 1607 and eventually set up the first permanent English settlement in the New World. They named it Jamestown. Despite two harsh winters, a catastrophic fire, conflict with natives, disease, starvation, and almost daily deaths, the settlement survived.

In June of 1608, Smith set out on another expedition to explore the boundaries of the entire bay. During two separate voyages spanning little more than three months, Smith and a crew of from 12 to 14 men sailed and rowed their 28-foot shallop roughly 2,500 miles across the length and breadth of Chesapeake Bay.

They explored every major watershed on both the eastern and western shores. Along the way, Smith kept notes on the bounty of land and sea. He documented native tribes’ languages and customs, charting the course for European colonization that eventually would spell those same tribes’ decline or outright extinction in the pursuit of a new nation.

A model replica of the sprit-rigged shallop used by Smith’s party to explore the boundaries of Chesapeake Bay. The vessel was shipped over in pieces and reassembled on site. Above is a wooden 1:32 kit available for assembly with detailed instructions from Dry-Dock Models & Parts.

Although John Smith is most famous for his historically dubious tale of the Powhatan Indian maiden Pocahontas saving him from execution, his more meaningful contribution came through copious letters, maps, and published writings about the Virginia Colony itself, especially those 1608 voyages.

In 1612, he published his book A Map of Virginia. With a Description of the Countrey, the Commodities, People, Government and Religion. Smith’s map and accompanying observations served as the primary source of information for generations of explorers and settlers in the bay region. Much later, his route served as inspiration for the nation’s first National Historic Water Trail, established in 2006.

Below are selected, lightly edited passages from his 1612 map and book, along with artwork depicting what it was like to explore the largest estuary on the Atlantic coast by small sailing craft more than four centuries ago.—editor

Watercolor illustration from the 1906 children’s book The Story of Pocahontas and Captain John Smith, written and illustrated by Elmer Boyd Smith. (Source)

A Map of Virginia. With a Description of the Country, Commodities, People, Government and Religion.

Written by Captaine John Smith sometimes Governour of the Countrey.

There is but one entrance by sea into this country, and that is at the mouth of a very goodly Bay, the widenesse whereof is neare 18 or 20 miles. The cape on the South side is called Cape Henry in honour of our most noble Prince. The shew of the land there, is a white hilly sand like unto the Downes, and along the shores great plentie of Pines and Firres.

The north Cape is called Cape Charles in honour of the worthy Duke of Yorke. Within is a country that may have the prerogative over the most pleasant places of Europe, Asia, Africa, or America for large and pleasant navigable rivers: heaven and earth never agreed better to frame a place for means of habitation being of our constitutions, were it fully manured and inhabited by industrious people. Here are mountaines, hils, plaine, valleyes, rivers, and brookes all running most pleasantly into a faire Bay compassed but for the mouth with fruitfull and delightsome land. In the Bay and rivers are many Isles both great and small, some woody, some plaine, most of them low and not inhabited. This Bay lieth North and South in which the water floweth neare 200 miles and hath a channell for 140 miles, of depth betwixt 7 and 15 fadome, holding in breadth for the most part 10 or 14 miles.


The country is not mountanous nor yet low but such pleasant plaine hils and fertle valleyes, one prettily crossing another, and watered so conveniently with their sweete brookes and christall springs, as if art it selfe had devised them.

Susquehanna River: The land of giants

Thirty leagues Northward is a river not inhabited, yet navigable; for the red earth or clay resembling bole Armoniack, the English called it Bolus.

There is one that commeth due north, 3 or 4 daies journy from the head of the Bay, and fals from rocks and mountaines. Upon this river inhabit a people called Sasquesahanock.

“Their attire is the skinnes of Beares and Woolves…”

—Captain John Smith

…60 of those Sasquesahanocks came to the discoverers with skins, Bowes, Arrowes, Targets, Beads, Swords, and Tobacco pipes for presents. Such great and well proportioned men, are seldome seene, for they seemed like Giants to the English, yea and to the neighbours: yet seemed of an honest and simple disposition, with much adoe restrained from adoring the discoverers as Gods. Those are the most strange people of all those Countries, both in language and attire; for their language it may well beseeme their proportions, sounding from them, as it were a great voice in a vault, or cave, as an Eccho. Their attire is the skinnes of Beares and Woolves, some have Cassacks made of Beares heades and skinnes that a mans necke goes through the skinnes neck, and the eares of the beare fastned to his shoulders behind, the nose and teeth hanging downe his breast, and at the end of the nose hung a Beares Pawe: the halfe sleeves coming to the elbowes were the neckes of Beares and the armes through the mouth, with pawes hanging at their noses. One had the head of a Woolfe hanging in a chaine for a Jewell; his Tobacco pipe 3 quarters of a yard long, prettily carved with a Bird, a Beare, a Deare, or some such devise at the great end, sufficient to beat out the braines of a man: with bowes, and arrowes, and clubs, sutable to their greatnesse and conditions.

Theses are scarse known to Powhatan. They can make neere 600 able and mighty men, and are pallisadoed in their Townes to defend them from the Massawomekes their mortall enimies. 5 of their chiefe Werowances came aboard the discoverers, and crossed the Bay in their Barge. The picture of the greatest of them is signified in the Mappe. The calfe of whose leg was 3 quarters of a yard about: and all the rest of his limbes so answerable to that proportion, that he seemed the godliest man that ever we beheld. His haire, the one side was long, the other shore close with a ridge over his crown like a cocks combe. His arrowes were five quarters long, headed with flints or splinters of stones, in forme like a heart, an inch broad, and an inch and a halfe or more long. These hee wore in a woolves skinne at his backe for his quiver, his bow in the one hand and his clubbe in the other, as is described.

Beastes of the New World

Of beastes the chiefe are Deare, nothing differing from ours. In the deserts towards the heads of the riuers, there are many, but amongst the riuers few.

There is a beast they call Aroughcun, much like a badger, but useth to live on trees as Squirrels doe. Their Squirrels some as neare as greate as our smallest sort of wilde rabbits; some blackish or blacke and white, but the most are gray.

A small beast they haue, they call Assapanick, but we call them flying squirrels, because spreading their legs, and so stretching the largenesse of their skins that they haue bin seene to fly 30 or 40 yards. An Opassom hath an head like a Swine, and a taile like a Rat, and is of the bignes of a Cat. Vnder her belly shee hath a bagge, wherein shee lodgeth, carrieth, and sucketh her young. Mussascus is a beast of the forme and nature of our water Rats, but many of them smell exceeding strong of muske. Their Hares [are] no bigger than our Conies, and few of them to be found.

Their Beares are very little in comparison of those of Muscovia and Tartaria. The Beaver is as bigge as an ordinary water dogge, but his legges exceeding short. His fore feete like a dogs, his hinder feet like a Swans. His taile somewhat like the forme of a Racket bare without haire; which to eate, the Savages esteeme a great delicate. They haue many Otters, which, as the Beavers, they take with snares, and esteeme the skinnes great ornaments; and of all those beasts they vse to feede, when they catch them.

There is also a beast they call Vetchunquoyes in the forme of a wilde Cat. Their Foxes are like our siluer haired Conies, of a small proportion, and not smelling like those in England. Their Dogges of that country are like their Wolues, and cannot barke but howle; and their wolues are not much better then our English Foxes. Martins, Powlecats, weessels and Minkeswe know they haue, because we haue seen many of their skinnes, though very seldome any of them aliue.

But one thing is strange, that we could never perceiue their vermine destroy our hennes, egges, nor chickens, nor do any hurt: nor their flyes nor serpents [to be] anie waie pernitious; where [as] in the South parts of America, they are alwaies dangerous and often deadly.

Of birds, the Eagle is the greatest devourer. Hawkes there be of diuerse sorts as our Falconers called them, Sparowhawkes, Lanarets, Goshawkes, Falcons and Osperayes; but they all pray most vpon fish. Patrridges there are little bigger then our Quailes, wilde Turkies are as bigge as our tame. There are woosels or blackbirds with red shoulders, thrushes, and diuerse sorts of small birds, some red, some blew, scarce so bigge as a wrenne, but few in Sommer. In winter there are great plenty of Swans, Craynes gray and white with blacke wings, Herons, Geese, Brants, Ducke, Wigeon, Dotterell, Oxeies, Parrats, and Pigeons. Of all those sorts great abundance, and some other strange kinds, to vs unknowne by name. But in sommer not any, or a very few to be seene.

Of fish [we] were best acquainted with Sturgeon, Grampus, Porpos, Seales, Stingraies whose tailes are very dangerous. Brettes, mullets, white Salmonds, Trowts, Soles, Plaice, Herrings, Conyfish, Rockfish, Eeles, Lampreyes, Catfish, Shades, Pearch of 3 sorts, Crabs, Shrimps, Creuises, Oysters, Cocles, and Muscles. But the most strange fish is a smal one so like the picture of S. George his Dragon, as possible can be, except his legs and wings: and the To[a]defish which will swell till it be like to brust, when it commeth into the aire.

Native planting and agriculture

They diuide the yeare into 5. seasons. Their winter some call Popanow, the spring Cattapeuk, the sommer Cohattayough, the earing of their Corne Nepinough, the harvest and fall of leafe Taquitock. From September vntill the midst of Nouember are the chiefe Feasts and sacrifice. Then haue they plenty of fruits as well planted as naturall, as corne greene and ripe, fish, fowle, and wilde beastes exceeding fat.

The greatest labour they take, is in planting their corne, for the country naturally is overgrowne with wood. To prepare the ground they bruise the barke of the trees neare the root, then do they scortch the roots with fire that they grow no more.

The next yeare with a crooked peece of wood, they beat vp the woodes by the rootes; and in that [those] moulds, they plant their corne. Their manner is this. They make a hole in the earth with a sticke, and into it they put 4 graines of wheat and 2 of beanes. These holes they make 4 foote one from another. Their women and children do continually keepe it with weeding, and when it is growne midle high, they hill it about like a hop-yard.

In Aprill they begin to plant, but their chiefe plantation is in May, and so they continue till the midst of Iune. What they plant in Aprill they reape in August, for May in September, for Iune in October. Every stalke of their corne commonly beareth two eares, some 3, seldome any 4, many but one, and some none. Every eare ordinarily hath betwixt 200 and 500 graines. The stalke being green hath a sweet iuice in it, somewhat like a sugar Cane, which is the cause that when they gather their corne greene, they sucke the stalkes: for as wee gather greene pease, so doe they their corne being greene, which excelleth their old.


The mildnesse of the aire, the fertilitie of the soile, and the situation of the rivers are so propitious to the nature and vse of man as no place is more convenient for pleasure, profit, and mans sustenance. Vnder that latitude or climat, here will liue any beasts, as horses, goats, sheep, asses, hens, &c. as appeared by them that were carried thither. The waters, Isles, and shoales, are full of safe harbours for ships of warre or merchandize, for boats of all sortes, for transportation or fishing, &c.

The Bay and riuers have much marchandable fish and places fit for Salt coats, building of ships, making of iron, &c.

Appearance and customs

6 or 700 have beene the most [that] hath beene seene together, when they gathered themselves to have surprised Captaine Smyth at Pamavnke, hauing but 15 to withstand the worst of their furie. As small as the proportion of ground that hath yet beene discouered, is in comparison of that yet vnknowne. The people differ very much in stature, especially in language, as before is expressed.

Some being very great as the Sesquesahamocks, others very little as the Wighcocomocoes: but generally tall and straight, of a comely proportion, and of a colour browne when they are of any age, but they are borne white. Their haire is generally black; but few haue any beards. The men weare halfe their heads shaven, the other halfe long. For Barbers they vse their women, who with 2 shels will grate away the haire, of any fashion they please. The women are cut in many fashions agreeable to their yeares, but euer some part remaineth long.

They are very strong, of an able body and full of agilitie, able to endure to lie in the woods vnder a tree by the fire, in the worst of winter, or in the weedes and grasse, in Ambuscado in the Sommer.


Each houshold knoweth their owne lands and gardens, and must liue of their owne labours.

For their apparell, they are some time couered with the skinnes of wilde beasts, which in winter are dressed with the haire, but in sommer without. The better sort vse large mantels of deare skins not much differing in fashion from the Irish mantels. Some imbrodered with white beads, some with copper, other painted after their manner. But the common sort haue scarce to couer their nakednesse but with grasse, the leaues of trees, or such like. We haue seen some vse mantels made of Turky feathers, so prettily wrought and wouen with threeds that nothing could bee discerned but the feathers, that was exceeding warme and very handsome. But the women are alwaies couered about their midles with a skin and [are] very shamefast to be seene bare.

They adorne themselues most with copper beads and paintings. Their women some haue their legs, hands, brests and face cunningly imbrodered with diuerse workes, as beasts, serpentes, artificially wrought into their flesh with blacke spots. In each eare commonly they haue 3 great holes, whereat they hange chaines, bracelets, or copper. Some of their men weare in those holes, a smal greene and yellow coloured snake, neare halfe a yard in length, which crawling and lapping her selfe about his necke often times familiarly would kiss his lips. Others wear a dead Rat tied by the tail.


In one of these huntings, they found Captaine Smith in the discoverie of the head of the river of Chickahamania, where they slew his men, and tooke him prisoner in a Bogmire; where he saw those exercises, and gathered these observations.One Savage hunting alone, vseth the skinne of a Deare slit on the side, and so put on his arme, through the neck, so that his hand comes to the head which his stuffed; and the hornes, head, eies, eares, and every part as arteficially counterfeited as they can devise. Thus shrowding his body in the skinne, by stalking he approacheth the Deare, creeping on the ground from one tree to another. If the Deare chance to find fault, or stande at gaze, hee turneth the head with his hand to his best advantage to seeme like a Deare, also gazing and licking himselfe. So watching his best aduantage to approach, hauing shot him, hee chaseth him by his blood and straine till he get him.

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