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Into The Unknown: The Pilgrims’ Adventurous, Risk-Taking Legacy


The following essay is part of The Federalist’s 1620 Project, a symposium exploring the connections and contributions of the early Pilgrim and Puritan settlers in New England to the uniquely American synthesis of faith, family, freedom, and self-government.

Come, my friends, ‘Tis not too late to seek a newer world … To sail beyond the sunset, and the baths of all the western stars. – “Ulysses,” Alfred Lord Tennyson

During the last month, contributors to The Federalist’s 1620 Project have demonstrated the resounding influence and positive legacy of the Pilgrims of the Mayflower and subsequent early sojourners to New England, such as the Puritans. Indeed, one can go far before overstating their invaluable endowment to the foundations of the American character.

The Pilgrims and emerging New Englanders made an additional contribution to the formation of the American ethos that is worth expanding upon, however: the daring, intrepid, and risk-taking qualities of those who settled in the northeast coast of what would become the United States. The resolve to pull up stakes and strike out into the perilous unknown — and the faith and fortitude to follow through on it — is an inspirational cultural debt we owe to the first early Pilgrims and New England settlers.

If instead of religious, freedom-seeking, young family units, arrivals on the northern shores of the future American coast had been the unwed, flighty, gold-seeking ruffians of the Jamestown variety, the America that followed would have been remarkably different.

While such a divergent alternative history is hard to conceive, the adaptive, adventurous, and trailblazing traits of the American character would assuredly be underdeveloped — even dormant — had our Pilgrim ancestors been too risk-averse to leave the Old World, cross the Atlantic, and doggedly hone their innovative habits in the untamed wilds of New England.

‘The Triumph of an Idea’

As Frederick Jackson Turner put it three centuries later, “Since the days when the fleet of Columbus sailed into the waters of the New World, America has been another name for opportunity.” The relatively sparse territory of the early 17th-century New England coast presented such an opportunity for the competent and resourceful — an opening the Mayflower Pilgrims seized.

The vast majority of the English Pilgrims at Leiden, Holland — numbering around 300 — chose not to risk it all in a daring crossing the Atlantic Ocean. Those who did, however, were, by the nature of their willingness to embark on such a perilous and risky undertaking, precisely the sort able to survive, then adapt, then thrive in a New World of their forging.

The early settlers of New England are, for Alexis de Tocqueville, the key to understanding America’s particular culture mores — a blend of equality, liberty, and religious faith. In his masterpiece “Democracy in America,” Tocqueville argues that, like Adam to the human race, the entirety of America’s destiny can be traced back to the first men and women to make landfall in modern-day Massachusetts.

Neither poor nor fabulously wealthy, the majority of the Pilgrims were what could be deemed “middle-class.” They left comfort, safety, and stability to brave the unexplored. “By exposing themselves to the inevitable hardships of exile,” Tocqueville explains, “they wanted to assure the triumph of an idea.” These men, women, and children proved to be willing and able to tolerate unnumerable setbacks and trials, as long as they could worship God in their own way and live out their lives in freedom.

The caricature of the Pilgrims and later Puritans as staid isolationists misses the mark. These folk weren’t pious sticks-in-the-mud — they were pious adventurers.

The Voyage

Before they reached New England soil, the Pilgrims suffered a voyage few modern Americans could endure. After numerous delays and losing a ship, the Speedwell, to repairs, the Pilgrims’ ticket to the New World, the Mayflower, finally set sail from England in September 1620.

It was not a ship built for transatlantic travel. At only 100 feet in length and 25 feet at her widest, the Mayflower was designed to cross the English Channel in short spurts, nothing more. “Cramped” does not begin to adequately describe the living quarters for the 102 passengers aboard, who had to share approximately 1,600 square feet of a wet, narrow hold amongst the ship’s largest timbers.

At night, the passenger area was pitch dark. At most, there was five feet of headroom — and only four where supportive beams stretched across the low deck. Aromas of the stench of the passengers mixed with the smells of overly ripe cheese, poorly preserved meat, vinegar, and, soon after reaching the high seas, vomit.

Of course, the challenges of a months-long winter crossing of the Atlantic in such an ill-suited vessel was only the beginning of the difficulties awaiting the Pilgrims. Even greater trials awaited them on cold, dry land.

‘A Wild and Savage Hue’

That the New England ground often froze by mid-November, and mere inches of snow made the terrain impenetrable without snowshoes were unwelcome hindrances to the Pilgrims, whose winters in England and Holland were far milder by comparison. Worse, as a few first Pilgrims disembarked the Mayflower to briefly explore Cape Cod, they felt the winter’s gale of what climatologists now refer to as the “Little Ice Age.” To their misfortune, the Pilgrims had made landfall during an exceptionally cold period that gripped the entirety of North America, and there was no turning back.

By early December, temperatures were in the low 20s Fahrenheit — a prolonged, biting cold foreign to anything typically experienced back home. As noted by future Plymouth governor William Bradford in his first-hand account, the Pilgrims had heard tales of the unforgiving winters of the northern New World. Still, it was one thing to hear tales of such conditions, and another thing altogether to experience them.

Furthermore, the Pilgrims headed into their venture truly alone. They knew no preexisting infrastructure or civilizational scaffolding would soften the blows of what faced them on the other end. They knew this, yet set out anyway. Bradford recalls:

They had now no friends to welcome them, no inns to entertain or refresh them … and, for the season it was winter, and they that know the winters of the country, know them to be sharp and violent, subject to cruel and fierce storms, dangerous to travel to known places, much more to search unknown coasts. … the whole country full of woods and thickets, represented a wild and savage hue.

No welfare systems nor expansive government-run social safety net was there to pick them up in hard times, nor to protect their embryonic, fragile settlements. Of course, they didn’t expect such things. During their first winter in the New World, they would need all of their resilience and all their faith to make it through. In addition, they’d have to be willing to welcome all the outside help they could get.

Trials to be Borne, Or Overcome

With temperatures intolerably cold, little food, and sickness ravaging the fledgling settlement, Plymouth Colony’s outlook was bleak. During the darkest months of the winter of 1621, Bradford writes that there were, at most, six of seven able Pilgrims who had to tend to the vital needs of the entire colony. “Willingly and cheerfully” and “without any grudging in the least,” these few heroic souls “spared no pains, night nor day,” and despite the hazards to their own health, fetched wood, made fires, fed the most hungry, and dressed and undressed the indisposed, sick, and dying.

In the end, of the original 102 who began the journey, only 50 were still alive come April. Nearly three out of every four women didn’t make it through.

Yet, through all of the challenges and setbacks faced by the Pilgrims in the early months, they kept their resolve and optimism. It would have been easy to turn back at the first available chance, to board the next vessel back to the Old World and return to their secure lives of the familiar and constant.

Yet few did. The challenges they faced were embraced, not shunned, and the Pilgrims viewed each impediment as a test to overcome. Bradford again so eloquently sums up this particular aspect of the dauntless Pilgrim spirit:

All great and honorable actions are accompanied with great difficulties, and must be both enterprised and overcome with answerable courages. It was granted the dangers were great, but not desperate; the difficulties were many, but not invincible. For though there were many of them likely, yet they were not certain; it might be sundry of the things feared might never befall; others by provident care and the use of good means might in a great measure be prevented; and all of them, through the help of God, by fortitude and patience might either be borne or overcome.

“They were willing to try just about anything if it meant they might survive their first year,” writes Nathaniel Philbrick in his essential “Mayflower: A Story of Courage, Community, and War.” Philbrick notes “the Pilgrims proved to be more receptive to the new ways of the New World than nearly any English settlers before or since.” This meant not just learning how to adapt and use the lands and resources of the Massachusetts wilderness, but the willingness to engage and even accept help from the non-Christian American Indians they encountered.

Taking Charge of Destiny

By all reason, a betting man in 1620 would have been forgiven for expecting the Plymouth Colony to fail, if not by the end of the first deadly winter, then soon thereafter. “That it had worked out differently,” says Philbrick, “was a testament not only to the Pilgrims’s grit, resolve, and faith, but to their ability to take advantage of an extraordinary opportunity.”

Given the prejudices of the time, and the haughty overconfidence of Europeans often displayed encountering non-Europeans, Plymouth’s residents would not have been out of step in dismissing all envoys from local American Indians in the region. Instead, they realized their best chance at learning how to survive lay with a policy of openness to new and innovative ideas, regardless of their source.

Peace treaties made with the Wampanoag chief Massasoit and the farming techniques learned from Squanto were key components to their success. “The Pilgrims might have insisted on a policy of arrogant isolationism,” Philbrick notes, “But by becoming an active part of the diplomatic process in southern New England they had taken charge of their own destiny in the region.”

The Pilgrims, however, also weren’t naïve about how quickly things could change. In February of 1622, to provide greater security for Plymouth, the Pilgrims embarked on a relatively massive building project: the edge of the colony was to be “impaled” with a wooden palisade wall.

Hundreds of trees from the surrounding area with felled with primitive axes. Large timbers of 10 to 12 feet were dug into a trench three feet deep. The wall, more than 2,700 feet in length and rising eight feet above the ground, was completed in the remarkable span of a single month. Despite their distance from potential European allies, the harsh terrain, and the ever-present threat of American Indians turning hostile, the Pilgrims were here to stay.

Into the Woods

Political philosophers remain reluctant to name “pragmatism” as America’s most symbolic contribution to philosophy (or to affirm that “pragmatism” is even a “philosophy” at all). It would, however, be well to note that the beneficial, continuous, small adaptations and adjustments that mark pragmatic actions go hand-in-glove with the actions necessary for the survival and eventual flourishing of the first settlers in New England — the very actions taken by the Pilgrims.

The religious beliefs of the Pilgrims played an undeniable role in the lives of the Plymouth colonists. Ultimately, however, it was their transition into rugged pioneers, and the innovation required to thrive in 17th-century New England that transformed them into an entirely new specimen: Americans.

Tocqueville argued “an American taken at random must be a man ardent in his desires, enterprising, adventurous, above all an innovator,” noting that the archetypal American carries this spirit wherever he goes, both “deep in the woods” as well as “within the cities.” The fearless, restless, risk-taking aspect of the frontiersman was, for Tocqueville, quintessentially American:

He fearlessly defies the Indian’s arrow and the diseases of the wilderness; the silence of the woods holds nothing that astonishes him … a stronger passion than love of life constantly spurs him on. Before him extends a continent nearly without limits, and you would say that, already afraid of having no room there, he hurries for fear of arriving too late.

The description Tocqueville paints of how adventurous Americans handle the unknown was seen, quite vividly, in the expansion of the eastern New England from Plymouth in 1620 to the wider Massachusetts Bay colony by the late 1670s.

A New, Endless Wave

Often forgotten in regaling the story of Plymouth Colony and its first inhabitants is that the progeny of the Pilgrims did not stay put for long. The initial act of deliberately breaking away from their home country and journeying thousands of miles across the open ocean awakened within the Pilgrims an appetite for freedom, one cultivated and fed by their early experiences establishing Plymouth Colony.

In 1630, a small armada of 17 ships bearing more than 1,000 eager settlers to the Massachusetts Bay area brought temporary wealth to Plymouth with the buying and exchange of land and animals. From that time on, however, immigration to the wider area continued, and the population of New England increased rapidly.

In the years to come, Pilgrim and Puritan colonists ventured south — planting the seeds of what would eventually become Connecticut — as well as north into territory now encompassed by the states of New Hampshire and Maine. Amidst this expansion, Plymouth’s most enterprising and wise inhabitants realized the town’s agricultural farming economy was unsustainable, and that Boston, with its exceptional harbor, held the destiny of the region.

Boston’s port access was the key to transatlantic trade, and New England fish and timber quickly become the envy of many European nations. As Philbrick notes, with only 20 percent of the land suitable for farming and its shallow anchorage, those that stayed in Plymouth past 1670 despite all the available land surrounding the greater Boston area and the opportunities in Massachusetts Bay, were, in effect, choosing to doom themselves to membership of the poorest colony in all of New England.

Many of Plymouth’s most famous names and closest friends of Bradford — among them, John Alden, William Brewster, Myles Standish, and Edward Winslow — saw the next great wave of opportunities beckoning, took their leave as soon as they had the chance, and founded towns to the north and west of Plymouth.

From Pilgrims to Rangers

It wasn’t long after the Pilgrims founded Plymouth that their love of independence flowered yet again. No second-generation resident of Plymouth Colony better represents the evolving adventurer-Pilgrim than Benjamin Church. Born in Plymouth Colony in 1639 and grandson of Mayflower passenger Richard Warren, Church was, as Philbrick notes, “one of the first New Englanders to embrace the wilderness.”

During King Philip’s War, Church served as captain of the force seen by many historians to be the forerunner to the U.S. Army Rangers. From his in-depth experiences with American Indians he both fought and befriended, Church developed tactics for frontier survival that aided homesteaders for centuries. His journeys took him beyond Massachusetts into Maine, New Brunswick, and what is now Nova Scotia before he passed away in Rhode Island.

Church, the next evolution of the Pilgrim, was in many ways a perfect embodiment of that word: a traveler; one from “over the lands”; a true American before there was a United States of America to speak of. As Everett S. Lee points out, “In America, we can say that migration is a part of our way of life. We are all but a few generations removed from our immigrant ancestors, whether they landed at Plymouth Rock or Ellis Island.”

What started out as a set of traits exemplified by English Pilgrims, later Puritans, then men like Benjamin Church, in time became the unique template for “the American,” full stop. As Tocqueville notes:

So it is the Americans who, daily abandoning the place of their birth, go to create for themselves vast domains far away. Thus the European leaves his cottage to go to inhabit the transatlantic shores, and the American, who is born on these very shores, disappears in turn into the emptiness of the central part of America. This double movement of emigration never stops: it begins in the heart of Europe, it continues across the great ocean, it keeps on across the solitude of the New World. Millions of men march at the same time toward the same point of the horizon: their language, their religion, their mores differ, their goal is shared.

That goal? Freedom. The chance to live one’s life as one sees fit; unmoored, and limited only by one’s talent, fortitude, and vision for the possibilities of what can be created beyond the next vista if we have the courage.