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Home Fairfield

The way we were

Westchester and Fairfield counties played key roles in the American Revolution

Georgette Gouveia by Georgette Gouveia
June 22, 2026
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Connecticut artist John Trumbull’s “Declaration of Independence” (1818, oil on canvas), which hangs in the United States Capitol Rotunda, is the quintessential American Revolutionary War-themed painting, one that looks back with nostalgia and ahead to the forging of a new nation. The Revolution itself was anything but as stately.

(See our America 250 special section coming out June 29.)

We tend to see the past not only through the lens of the present but through those of nostalgia and distance. So it is with the American Revolution, which often appears like the  dignified tableaux in Connecticut artist John Trumbull’s paintings.

“John Trumbull was not just an artist of the Revolution; he was also a participant, serving as an aide-de-camp to George Washington,” said Carey Mack Weber, the Frank and Clara Meditz executive director of the Fairfield University Art Museum (FUAM), whose “For Which It Stands…” exhibit explores the American flag as a symbol of patriotism and protest through July 25. “Trumbull created many of his most famous paintings decades after the war, in the early 19th century, when the young republic was still defining itself. He responded to the strong cultural need to stabilize the memory of the Revolution, to turn it from a divisive, uncertain struggle into a shared founding myth. His paintings helped do exactly that. They emphasize unity over conflict, leadership over disorder and principle over violence. So, (it) is not simply personal nostalgia; it’s also nation-building.”

Yet, as Weber alluded, the Revolution (1775-1783) was a brutal struggle and more, a transatlantic war involving not only the colonies and Great Britain but France, Spain, the Dutch Republic and Hanover (Germany) in encounters from Canada to the Caribbean and as far west as what is now the Midwest. As depicted in filmmaker Ken Burns’ latest PBS series, “The American Revolution,”  it was also the fledgling United States’ first civil war, American against American in a zero-sum struggle for identity and independence with echoes for our own time of partisanship and violence, courage and resilience.

The conflict had actually begun a decade earlier as a fight with Parliament for socioeconomic equality. (See the Stamp Act of 1765.) Still, as tensions escalated, only about one-third of the colonists chaffed under British rule, while a third or less were loyal and another third neutral. But once the rebels, or Patriots, realized that there could be no economic freedom without political freedom, the focus of ire shifted to King George III as a perceived tyrant, and the fight became more savage, visceral and existential as the Patriots went all in to eliminate the Loyalists and neutral parties like the Quakers by any means possible.

“You’re fighting a desperate war,” said local historian and tour guide Stephen Paul DeVillo, author of four books, including “The Battle of White Plains” and the recent “Westchester County in the American Revolution: A Neutral Ground” (The History Press/Arcadia Publishing, 143 pages, $24.99). “If you’re not for us, then you’re the enemy….In the end, all conflicts are us versus them.”

A map of the Battle of White Plains (Oct. 28-Nov.1, 1776), published on Jan. 1, 1792. Courtesy the Digital Collections of the New York Public Library.

The not so ‘Neutral Ground’

While that desperation permeated the 13 colonies, it had a particularly searing cast in our area, where Westchester and Fairfield counties played key roles in an all-or-nothing play for freedom.

About 10% to 25% of New York, then the second largest city in the colonies after Philadelphia, burned to the ground on Sept. 20 and 21, 1776, shortly after the British took possession of it. They wouldn’t leave the city until Nov. 25, 1783.

To the north, the “Neutral Ground” of Westchester — so called for the formidable array of geographical features, formed by the Ice Age 22,000 years ago, that made it difficult for either side to gain traction – lived up to its billing at first. Indeed, even perhaps its most famous conflict, the Battle of White Plains (Oct. 28-Nov.1, 1776) – with British Commander in Chief William Howe advancing on Chatterton Hill (now Battle Hill), where some of Continental Army Commander in Chief George Washington’s forces were arrayed, the rest being entrenched between the Bronx River and West Harrison – was a draw, DeVillo said, as British forces quit the field, and the Continental Army headed north to Fishkill and ultimately New Jersey.

Far from becoming insulated, however, Westchester and The Bronx – which formed one of the wealthiest counties in the colonies – became a devastated no man’s land of skirmishes, espionage and raids, with residents terrorized by both the pro-Patriot Skinners gang and the pro-British Cow Boys, a pejorative term, DeVillo said, that marked the first appearance of “cowboy” in the American lexicon.

In “The American Revolution: An Intimate History” (Alfred A. Knopf, $80, 581 pages), the companion to Burns’ film, co-author Geoffrey C. Ward writes: “Timothy Dwight, a Continental Army Congregational chaplain and future president of Yale, never forgot what he saw there:  ‘The unhappy inhabitants were exposed to the depredations of both (armies)…They feared everybody who they saw and loved nobody.’”

And yet, out of this traumatized wasteland would come some of the most crucial contributions to the Revolutionary cause – including the July 9, 1776 approval of the Declaration and formation of New York state at the Fourth Provincial Congress of New York in White Plains; the 1780 capture near Tarrytown of British Major John André, who carried plans for West Point that might have struck the death blow to liberty; and Washington’s fateful 1781 decision, made at the Odell House in Greenburgh, to forgo trying to retake New York in favor of trapping the British at Yorktown, thus ending the war.

Brown Bess musket, powder horn and cannon balls. Courtesy Greenwich Historical Society.

Connecticut to the rescue

“Ground Zero”:  That’s how Kathy Craughwell-Varda, senior curator of Greenwich Historical Society, describes Connecticut’s “little understood” role in the American Revolution:

“Lost in the story was how terrifying and daunting it was to live in Revolutionary coastal Connecticut.”

Fairfield County was the gateway to Patriot New England, where Greenwich (population 2,788 at the time) sent money to aid Boston during the British blockade of the city (April 19, 1775-March 17, 1776). Months later, starving Greenwich residents would hear the cannon fire from the Battle of White Plains, Craughwell-Varda added.

Connecticut itself didn’t lack ammunition. It would make 42,000 musket balls from pieces of the  lead and gilded equestrian statue of George III that New Yorkers took down from Manhattan’s Bowling Green after the reading of the new Declaration of Independence on July 9, 1776 in what is now City Hall Park. (The horse’s swirling tale is preserved at The New York Historical, as seen on PBS’ “Lucy Worsley Investigates: The American Revolution.”)

Meanwhile, Connecticut sea captains turned privateers captured almost 500 British ships. But Great Britain destroyed the supply depot in Danbury on April 25, 1777.

Two days later, however, at the Battle of Ridgefield, 700 Connecticut militiamen — under such generals as Benedict Arnold, a brilliant, charismatic field commander who had not yet betrayed the Patriot cause – galvanized the colony as they took a heroic stand against 1,800 British soldiers fighting their way back to the sea. Though the British would burn Fairfield and Norwalk in 1779, they would never again attempt a Connecticut invasion, freeing the militia for its key role in the turning point of the war, the Patriot victory at the Battle of Saratoga, New York, (Sept. 19, and Oct. 7, 1777).

Fairfield and its strategic Long Island Sound Shore location would also prove vital as Patriots gathered information from the Long Island-based Culper Ring, Washington’s spy network.

The introductory gallery of Greenwich Historical Society’s “Fashioning America: 250 Years of Greenwich Style,” on view through Jan. 20. Courtesy Greenwich Historical Society.

A nation – and a history – for all

In telling the story of the Revolution that spawned a new country based on democratic ideals for everyone, local civic and cultural leaders have stressed the need to remember the contributions of Native Americans and enslaved and free Black Americans, who fought on both sides in an attempt to secure an advantage for themselves and their people; and of women, who raised funds and nursed the sick and wounded behind the front lines while also tending to children and home.

In “The American Revolution,” Ken Burns recounts the story of women, led by Esther de Berdt Reed and the Ladies Association of Philadelphia, who in 1780 raised more than $300,000 in Continental currency to support the Continental Army – only to be rebuffed by Washington. The men, he said, would only waste it on drink. Shirts were what was needed. So the women used the funds to purchase linen and sew 2,000-plus shirts for soldiers. It’s one of the most haunting motifs in Burns’ series as he imagines Patriot women — skirts hoisted and legs bare – wading into rivers to wash such clothing, its blood stains mingling with the water.

“History is a lesson,” Westchester County Executive Kenneth W. Jenkins said. “To try to erase it or manipulate it is doing a disservice to all those folks who worked hard to be included in that ‘more perfect union.’”

It’s also the story of those who didn’t want to be part of that union (the Loyalists) or the fight (including pacifists like the Quakers). And then there were those like David Bush, the largest land and slave holder in Greenwich, who played both sides, running afoul of each. Though his businesses suffered, his property was left unscathed. (His home is now Greenwich Historical Society’s Bush-Holley House.) Others, not so lucky, were bedeviled, devastated and driven out.

Craughwell-Varda understands those who were reluctant to join or opposed the Patriot cause:

“It was not a simple choice. You were picking a side with a makeshift army and a general (Washington), who rarely won any battles.”


Keith Mayerson’s “First Men on the Moon,” (2012, oil on linen). From Fairfield University Art Museum’s “For Which It Stands…,” on view through July 25. © 2012 Keith Mayerson.

A living legacy

In a way, the Revolution in Westchester and Fairfield counties was a microcosm of the larger war, a bloody enterprise that meandered from New England through the middle Atlantic states to the South, with the British winning many battles but never striking the decisive blow. It’s one of the lasting questions of the Revolution:  Why did the British lose North America? When I posed this to British historian Simon Schama after the publication of his 2006 book “Rough Crossings: Britain, the Slaves and the American Revolution,” he said, “Because they never understood it. And you can’t hold what you don’t understand.”

Local historian DeVillo pointed to 18th-century Britain as the world’s preeminent naval power but with a  smaller army, an empire that built itself “from the sea out rather than the sea in.” Having led British troops to victory in the Battle of Bunker Hill (actually Breed’s Hill, June 17, 1775) and seen the casualties the Americans could exact, DeVillo added, British Commander in Chief Howe may have been reluctant to expend so much blood on a cause that the British believed would somehow favor them in the end.

“The British overestimated the number of Loyalists,” DeVillo said, a hubris that along with an ignorance of the tough American climate, terrain and character would prove particularly fatal and fateful at Saratoga, convincing archenemy France to enter the war on the Patriot side.

The French contribution cannot be underestimated but neither can the Patriots’ willingness in the face of British brutality to double down, give as good as they got and endure.

Yet what if the Patriots hadn’t? DeVillo said we probably would’ve become a country like Canada, part of the British Commonwealth. That might’ve had profound implications for World Wars I and II, in which our independence enabled us to build up the manpower and industrial might to enter those wars late but decisively.

Was that involvement a blood debt we owed Continental Europe for its help in the Revolution? When the American Expeditionary Forces (AEF) arrived in Paris in 1917, Col. Charles E. Stanton, aide to AEF commander Gen. John “Black Jack” Pershing, stood before the grave of the Marquis de Lafayette, who had fought for American independence under Washington, and said, “Lafayette, nous voilà” (“Lafayette, we are here.”)

But Aaron Q. Weinstein, Ph.D., an assistant professor of politics at Fairfield University and faculty liaison to Fairfield University Art Museum’s “For Which It Stands…” exhibit, said that in the end, the Revolution and the nation it spawned are not about blood debt but birthright.

“America has a birthright of democracy,” he said, one that has a stake in seeing people live freely around the world. It’s a tale, he added, whose origins are not that far removed from us, a mere 10 to 12 generations:

“It’s a living story.”

 

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