The Plymouth branch of the Virginia Company got started first when, in August 1606, a ship captain named Henry Challons took about thirty men to the northern part of the assigned territory. But without any previous experience, or even a competent guide aboard, the expedition quickly lost its way in the strange waters and was finally captured by a Spanish fleet in the West Indies. A second attempt proved even less successful; this one returned to England within a few weeks without ever even having seen the American continent.
Finally, one of the Virginia Company’s major investors decided to take matters into his own hands. In 1607, Sir Ferdinand Gorges financed an expedition of his own, sending out about a hundred men under the leadership of Raleigh Gilbert, nephew to Sir Walter Raleigh. They reached the New England coast around the middle of the year, and near the Kennebec River they built themselves a few shelters, a church, and a protective fort, and settled down to the business of colonizing. But there were problems from the very first. There was a shortage of food and supplies; the weather proved “extremely unreasonable and frosty,” and the natives of the area proved obstinately hostile. There was no gold or silver, of course, and before long many of the disillusioned settlers began to sulk and to squabble among themselves. A vicious New England winter finished off whatever good intentions might have remained, and by the spring of 1608, the survivors of this battered outpost returned to Olde England, thereby ending the Plymouth Company’s efforts in America.

The London branch of the Virginia Company had meanwhile begun its own enterprise. In December 1606, in the dead of winter, three small ships – the Godspeed, the Discovery, and the Susan Constant – carried 120 men westward across the Atlantic under the command of Admiral Christopher Newport. Winter on the North Atlantic quickly made true believers of all the travelers. Not until the middle of May did the three ships finally reach the coast of Virginia at Chesapeake Bay, their passenger list now reduced to 104. The shaken survivors gratefully named the land before them Point Comfort; the two capes at the bay’s entrance became Capes Henry and Charles, in honor of members of the royal family.
On board one of the ships, the expedition carried a sealed box containing detailed instructions from the governing council in England, to be opened on their arrival in Virginia. Included, too, were the names of the men who were to be the governing councilors in Virginia: Master Edward Wingfield and Captains Bartholomew Gosnold, John Smyth, John Ratliffe, John Martin, and George Kendall. The men were instructed to find a healthful place for their settlement, a safe harbor in a navigable river, and to prepare themselves against attacks – by the natives, who were expected to be hostile, or by the Spaniards, who presumably would soon object to the English presence in the New World. No man was to be allowed to abandon the settlement without company permission, and no one was to write home any discouraging letters. And in order to prevent problems as much as possible, the settlers were further instructed to avoid “giving offence to the naturals.”
Despite their explicit instructions, the leaders of the new colony immediately proceeded to make a most serious error. After considerable and solemn discussions, they chose a site for their settlement about thirty miles upstream along the banks of a stream they had already named the River James. They could hardly have chosen a worse location: the low, swampy land, covered with dense brush, infested with mosquitoes, surrounded by mostly hostile Indians, would claim nearly half the settlers within the first six months. Before they had even had a chance to settle down, in fact, some of the Indians of the area made it clear what they thought of their new neighbors – in a sudden attack they killed two of the Englishmen and wounded about a dozen more. Still, all the men dutifully wrote glowing accounts of the country around them – of the beautiful and exotic flowers, of the abundance of fish and fowl and game. All the fruits and edible plants were enormous and the most delicious they had ever tasted – including strawberries, “foure times bigger and better than ours in England.” And all through this rich and fruitful land there flowed the River James, “one of the famousest” ever found by a Christian expedition.
The colony’s leaders had been instructed to put one group to work on housing and fortifications, another to plant crops, while a third group was to “discover . . . the country about you.” A storehouse, a church, and some primitive houses were actually constructed, along with fortifications of some sort, and the place was named James Cittie, in honor of the King of England, their nominal sponsor. Little else was accomplished; as one of the councilors, John Smith, later wrote, there was “no hope, no talke, no worke, but dig gold, refine gold, load gold.”
A small exploration party was eventually assembled, and they set out to ‘discover’ the James River and the surrounding areas. In the course of their wanderings they came on a group of Indians of the Powhatan Confederacy. Their chief’s name was Wahunsonacock, but the English quickly decided to call him by his tribe’s name. At any rate, to show their peaceful intentions, the white men plied Chief Powhatan with alcoholic drinks, which “staggered the potentate” much to the amusement of the English. There were to be many more encounters with the natives of Virginia, but few would prove as peaceful or as amusing as this first one.
It was one such encounter that produced the beginnings of the first of many intriguing legends of early America. In December of that first year, Captain John Smyth – or John Smith, as he has come down through history – lead another expedition up the Chickahominy River in search of food for the settlement, and in the process they were captured by the Powhatan Indians, who had apparently already become disenchanted with their new white neighbors. Before the Indians could proceed with the customary torture of their prisoners, however, the daughter of Chief Powhatan threw herself over Smith and protected him from harm – or so legend has it. The authenticity of the tale is still a most controversial subject, particularly since Smith turned out to be the only survivor of this expedition. The girl, at any rate, was a very real person. Her native name was Matoaka, though somehow she became known to the English at Jamestown as Pocahantas, and Jamestown would see much more of Pocahantas in later years.