Jamestown and Plymouth Rock: Foundations of America

We look at the many differences, and similarities of these two foundational colonies.  

Transcript

Jamestown and Plymouth Rock: Foundations of America

April 2026

"Now, all of us at Jamestown beginning to feel that sharp prick of hunger, which no man truly describe, but he which have tasted the bitterness thereof." — George Percy, on the "Starving Time" of 1609-1610.

“Thus out of small beginnings greater things have been produced by His hand that made all things of nothing, and gives being to all things that are; and, as one small candle may light a thousand, so the light here kindled hath shone unto many...”
 ― William Bradford, Bradford: Of Plymouth Plantation

I would love to simply put down my marker and say THIS is the foundation of America.  Yet, like presidential elections and people liking The Bachelor, the answer is not one or two reasons but multi-causal.  However, two concepts: that of religion and commerce, both linked by the pursuit of greater liberty, are certainly two aspects of the American character from the beginning.  I wanted to explore those concepts in parallel, given that both are celebrated as the first English settlements in North America.  

Jamestown (founded 1607) and Plymouth Rock (associated with the 1620 landing of the Pilgrims) occupy a central place in the history of colonial America. While both represent foundational moments in English colonization of North America, they differed significantly in purpose, social structure, economic organization, and long-term development. At the same time, they shared common challenges and contributed to broader patterns that shaped the future United States.  And the critical pattern here, as we shall see, is liberty.  

Jamestown, established by the Virginia Company, was primarily a commercial venture. Investors hoped to find gold, natural resources, and a profitable route to wealth. The settlers, many of whom were gentlemen unaccustomed to manual labor, initially struggled to survive. The colony’s early years were marked by disease, starvation, and conflict with Indigenous peoples, particularly the Powhatan Confederacy. Leadership figures such as John Smith imposed strict discipline that helped the colony endure. Over time, Jamestown achieved economic stability through tobacco cultivation, largely due to the efforts of John Rolfe. This crop became the economic backbone of Virginia. It encouraged the expansion of plantation agriculture, which in turn led to the growth of indentured servitude and eventually the institutionalization of African slavery.

On December 6, 1606, the journey to Virginia began on three ships, though without the notoriety of Columbus’ trio nor the remembrance of the Mayflower.  Yet as a guy who spent three decades in business, the names resonate with me as much as those of other crafts.  The ships were the Susan Constant, the Godspeed, and the Discovery. In 1607, 104 Englishmen and boys arrived in North America to start the settlement. On May 13, they picked Jamestown, Virginia, to be named after King James I. This, and not the later Plymouth Rock, was the first true English settlement in North America.

The site for Jamestown was chosen for several reasons, all of which met the criteria set by the Virginia Company. The site was surrounded by water on three sides for easy commercial access, yet far enough inland to defend against possible Spanish attacks. Notably, the English had greater concern about Spanish attacks than about native Americans or the French, who had founded a Canadian settlement at Port Royal in 1605.  The water was also deep enough that the English could tie their ships at the shoreline - good parking! The site was also not inhabited by the Native population.

Once the spot was chosen, the instructions sent by the Virginia Company, with the list of the council members (chosen by officials in England), were read. The names were kept in a sealed box on the ship (each ship had a sealed copy). The first President of the new Virginia colony was to be Edward Maria Winfield. The other six council members were: Bartholomew Gosnold, Christopher Newport, John Martin, John Ratcliffe, George Kendall, and (the one we all remember) John Smith.

By June 15, the fort was completed. It was triangle-shaped with a bulwark at each corner, holding four or five pieces of artillery. The settlers were now protected against any attacks by the local Powhatan Indians, whose hunting land they were living on. Relations had already been strained between the newcomers and the Powhatan Indians when, on June 22, Newport left for England to obtain more supplies.

Not long after Newport left, the settlers began to succumb to various diseases. It did not help that they were drinking water from the salty or slimy river.  Natural deaths occurred from swellings, fluxes, fevers, and famine.  Food was running low despite Powhatan sending occasional gifts. In fact, if not for the Powhatan Indians’ help in the early years, the settlement would most likely have failed, as the English would have died from the various diseases or starved. Yet the settlement did endure.  

By late 1609, the relationship between the Powhatan Indians and the English had soured, as the English demanded too much food during a drought. That winter of 1609-10 is known as the “Starving Time.” During that winter, the English were afraid to leave the fort, due to a legitimate fear of being killed by the Powhatan Indians. As a result, they ate anything they could: various animals, leather from their shoes and belts, and sometimes fellow settlers who had already died. By early 1610, most of the settlers, 80-90% according to William Strachey, had died due to starvation and disease.

In May 1610, shipwrecked settlers who had been stranded in Bermuda finally arrived at Jamestown. Part of a fleet sent the previous fall, the survivors used two boats built in Bermuda to get to Jamestown. Sir Thomas Gates, the newly named governor, found Jamestown in shambles with the palisades of the fort torn down, gates off their hinges, and food stores running low. The decision was made to abandon the settlement. Less than a day after leaving, however, Gates and those with him, including the survivors of the “Starving Time,” were met by news of an incoming fleet. The fleet was bringing the new governor for life, Lord Delaware. Gates and his party returned to Jamestown.

In 1612, John Rolfe, one of many shipwrecked on Bermuda, helped turn the settlement into a profitable venture. He introduced a new strain of tobacco from seeds he brought from elsewhere. Tobacco became the long-awaited cash crop for the Virginia Company.

Kate Egner, writing for the American Battlefield trust notes in her article “Everyday Life in the Jamestown Colony,” notes, “After John Rolfe’s successful experiments with the crop tobacco quickly became the profitable export England was hoping for from the Jamestown venture. Tobacco production, however, was labor intensive. Men, women, and even children contributed to the cultivation of their family’s tobacco crop—clearing fields of trees, planting the tobacco seeds, weeding the crops and “topping” the plants, and removing the tobacco worms that threatened to destroy the crop. Harvesting the leaves to prepare them for export involved even more time and labor.”

On July 30, 1619, newly appointed Governor Yeardley called for the first representative legislative assembly. This was the beginning of representative government in what is now the United States of America.

In that same year, the first documented Africans were forcibly captured and brought to Virginia to work the tobacco fields. It is contested whether, at the time, these people were considered indentured servants or enslaved people; however, historical evidence suggests they were often treated in a manner that more closely resembles enslavement as we understand it today.

As historian James Horne notes of Jamestown, “At Jamestown the English learned the hard lessons of sustaining a colony. All successful English colonies followed in its wake, but Jamestown also presents two sides of America’s founding. On the one hand, England’s New World offered many settlers opportunities for social and economic advancement unthinkable at home; while on the other, colonization unleashed powerful destructive forces that were catastrophic for Indian peoples, whose lands were taken by colonists, and for enslaved Africans and their posterity, whose labor enabled Jamestown, and indeed America, to flourish.”

As noted, Jamestown was founded by a for-profit company and was seen by all as a money-making venture.  In contrast, the settlement associated with Plymouth Rock was founded by religious dissenters known as the Pilgrims, who were seeking freedom from persecution in England. Though their initial funding came from a for Profit venture, this expedition was different not just from Jamestown but pretty much everything that came before.

Yet, as Historian Christopher Caldwell writes in his piece “Plymouth Rock Landed on Them” states, “What was unique about the Pilgrims, even among other English settlers of their time, is that they came for love of God, not love of money. From Columbus’s voyages until the settlement of Virginia, explorers and exploiters had taken great risks—but always for their own enrichment (and at one remove, a monarch’s glory). “It was reserved for the first settlers of new England,” said Adams, “to perform achievements equally arduous, to trample down obstructions equally formidable, to dispel dangers equally terrific, under the single inspiration of conscience.” 

The core group (roughly 40 percent of the adults and 56 percent of the family groupings) was part of a congregation led in America by William Bradford and William Brewster and was initially known as Separatists. They had begun to feel the pressures of religious persecution by the Church of England while still in the English village of Scrooby, near East Retford, Nottinghamshire. In 1607, Archbishop Tobias Matthew raided homes and imprisoned several members of the congregation. 

The congregation left England in 1608 and moved to the Netherlands, settling first in Amsterdam and then in Leiden.  In Leiden, the congregation gained the freedom to worship as they chose, but Dutch society was foreign to them. Scrooby had been an agricultural community, whereas Leiden was a thriving industrial center, and they found the pace of life difficult. The community remained close-knit, but their children began adopting Dutch language and customs, and some also enlisted in the Dutch Army. They were also still harassed by the English Crown: English authorities came to Leiden to arrest William Brewster in 1618 after he published sharp criticism of the King of England and the Anglican Church. Brewster escaped arrest, but the events spurred the congregation to move farther from England.

The congregation obtained a land patent from the Plymouth Company in June 1619. They had declined the opportunity to settle south of Cape Cod in New Netherland because they sought to avoid Dutch influence. They obtained financial backing through the Merchant Adventurers, a group of businessmen who sought to profit from the colony once the Pilgrims began working to repay their debts.

 With the funds secured from the Merchant Adventurers, the Colonists bought provisions and obtained passage on the Mayflower and the Speedwell. They had intended to leave early in 1620, but they were delayed several months by complications with the Merchant Adventurers, including several changes in plans for the voyage and financing. The congregation and the other colonists finally boarded the Speedwell in July 1620 in the Dutch port of Delfshaven. 

Other passengers joined the group in Southampton, including William Brewster, who had been in hiding for the better part of a year, and a group known to the Leiden congregation as “The Strangers”, extra workers and staff largely recruited by the Merchant Adventurers. The term was also used for many of the indentured servants who paid for their passage by binding themselves to a period of service.

Among the Strangers were Myles Standish, who was the colony’s military leader; Christopher Martin, who the Merchant Adventurers had designated to act as shipboard governor during the trans-Atlantic trip; and Stephen Hopkins, a veteran of a failed colonial venture that may have inspired Shakespeare’s The Tempest. The group that later became the Leiden Leaders after the merging of ships included John Carver, William Bradford, Edward Winslow, William Brewster, and Isaac Allerton. 

After the Speedwell began to leak, the plan was to abandon that ship and make the passage on the one ship left to the settlers.  The Mayflower departed Plymouth, England, on September 6, 1620, with 102 passengers and about 30 crew members on the 106-foot-long ship. The seas were not severe during the first month in the Atlantic, but in the second month, the ship was badly shaken by strong north Atlantic winter gales, causing leaks from structural damage. There were many hardships and dangers throughout the trip, including seasickness and the bending and cracking of a main beam of the ship. Miraculously, only one death occurred, that of William Button.

After two months at sea, which must have been harrowing for the passengers, they sighted land on November 9, 1620, off the coast of Cape Cod. They attempted to sail south to the designated landing site at the mouth of the Hudson but ran into trouble at Pollock Rip, a shallow area of shoals between Cape Cod and Nantucket Island. With winter approaching and provisions running dangerously low, the passengers decided to return north to Cape Cod Bay and abandon their original landing plans.

The Plymouth Rock settlers established the Mayflower Compact, a foundational document that created a framework for self-government based on majority rule. This agreement reflected a more collective, community-oriented approach than Jamestown’s corporate structure. Leaders like Bradford emphasized cooperation, moral discipline, and religious devotion.

Economically, Plymouth differed from Jamestown in lacking a single lucrative cash crop. The settlers relied on subsistence farming, fishing, and trade.  Similar to Jamestown, their survival was significantly aided by assistance from Native Americans, especially Squanto, who taught them local agricultural techniques, such as planting corn. Relations with Indigenous peoples, particularly the Wampanoag Confederacy under the leadership of Massasoit, were initially cooperative and mutually beneficial, in contrast to the more conflict-ridden interactions seen in early Jamestown. 

Caldwell adds, “The Englishmen who explored Massachusetts Bay did nothing to make themselves especially welcome. In the decade before the Pilgrims arrived, there had been various incidents in which natives, dozens in total, had been invited on board French, English, Dutch, or Spanish ships and kidnapped, either to be trained as guides or sold as slaves. One of these was Squanto, captured near Plymouth in 1614, who escaped from the Spanish slave port of Málaga to London and made his way back to his native Plymouth. The Pilgrims, naïve about this history, blundered into a war zone. They themselves stole buried corn in their first hungry days in the New World, and were greeted with a shower of arrows on their first encounter with Indians. They did plenty of fighting, led by a secular mercenary named Myles Standish—brave, erudite, underhanded, and so diminutive that he was known (though not to his face) as “Captain Shrimp.” But even decades later, as tension rose between nearby colonies and nearby Indians, the Pilgrim-Wampanoag peace held.”

One concept omitted by certain historians is that many Native American leaders were at war or hard-pressed by larger tribes.  The Wampanoag and Mohegan, allied with English colonists, sought protection against the powerful and dominant Narragansett tribe. The need for security against Narragansett expansion, tribute demands, and territorial disputes often drove these alliances. 

In the Fall of 1621, the Pilgrims famously shared a harvest feast with the Pokanokets; the meal is now considered the basis for the Thanksgiving holiday. It took place over three days, from late September to mid-November, and included feasting, games, and military exercises.

Most of the attendees at the first Thanksgiving were men; 78 percent of the women who traveled on the Mayflower perished over the preceding winter. Of the 50 colonists who celebrated the harvest (and their survival), 22 were men, four were married women, and 25 were children and teenagers.

The Pilgrims were outnumbered more than two to one by Native Americans, according to Edward Winslow, a participant who attended with his wife and recorded what he saw in a letter, writing: “many of the Indians coming amongst us, and amongst the rest their greatest king Massasoit, with some ninety men.”

Socially and politically, the two colonies developed along different lines. Jamestown evolved into a hierarchical society dominated by landowners and governed initially by company officials, later transitioning to royal control. It also established one of the first representative assemblies in America, the House of Burgesses, in 1619. Plymouth, on the other hand, maintained a more egalitarian structure, with governance rooted in religious principles and community consent. While not fully democratic by modern standards, Plymouth allowed broader participation among male church members.

Even at this point, we can see the roots of the differentiated approach to lifestyle.  Larger farms, focused on a single cash crop in the South, with slaves to manage the work.  Small farms, multiple crops, religious fundamentalism, and indentured servitude, but not a large slave contingent

Despite their differences, Jamestown and Plymouth shared several important similarities. Both colonies faced severe hardships in their early years, including harsh winters, food shortages, and disease. Survival in both cases depended on strong leadership, adaptation to local conditions, and interactions—whether cooperative or conflictual—with Indigenous populations. And both were founded on liberty: in the South, economic; in the North, religious.  

During the Revolutionary War, the English called New England the hotbed of the Revolution.  One campaign in 1777 was intended to build a series of forts along the Hudson to cut off New England from the rest of the colonies. After all, opposition to the Stamp Act or taxes on tea was centered in Boston.  And from New England came Sam Adams, John Adams, and the President of the Continental Congress, John Hancock.  Yet consider that the writer of the Declaration of Independence and the leader of the armed forces of the Revolution were both Virginians. And it was a third Virginian who declared, " Give me liberty, or give me death.  

Both settlements laid the groundwork for future English expansion in North America, helping to establish patterns of settlement, governance, and economic activity.

In terms of long-term impact, Jamestown’s legacy is closely tied to the development of the Southern colonies, particularly its reliance on cash crops and labor systems that would shape the region’s economy and social hierarchy. Plymouth’s influence is more closely associated with 

New England traditions of community governance, religious motivation, and education. Together, these two colonies illustrate the diversity of motives and experiences that characterized early English colonization.

While Jamestown and Plymouth Rock were both pivotal early English settlements, they differed fundamentally in purpose—profit versus religious freedom—economic structure, social organization, and relations with Indigenous peoples. Yet they also shared the common challenge of survival in a new and often hostile environment, and both produced people united in achieving freedom.