Native American Settlements
and Contact with English Colonists |
The Great Swamp Fight | English Settlement at Uncoway
| Division of the Long Lots and Commons |
The Burning of Fairfield during the American Revolution |
Patriots and Loyalists | Slavery and
Slave Owners in Fairfield | Sources of Prosperity:
Agriculture and Maritime Commerce | The Arrival of the
Railroad | New Neighbors: Immigrants of the 19th and Early
20th Centuries | Modern Highways
The following information is drawn from the
Fairfield Museum and History Center’s core exhibition, Landscape of Change.
Please visit the history center's web site
for more information.
Native American Settlements and Contact with English Colonists
Fairfield’s coastal geography and plentiful natural resources attracted humans
for thousands of years before European settlers stumbled upon the “fair fields”
that Native Americans called Uncoway. This area provided indigenous peoples with
game, fish, abundant sweet water, and fertile land to cultivate. During the Late
Woodland Period (1500-1650), Uncowas, Sasquas, Maxumux, and Pequonnocks—subdivisions
of the Paugussett Indians—inhabited the coastal areas, locating their villages
of wigwams along the inland waterways. Another clan of Paugussetts called the
Aspetucks occupied land several miles further inland, in the area that is now
Weston and Easton.
The Native American population of southern New England was probably quite large
before contact with European explorers. However, in the early 1600s epidemics of
smallpox, measles, and other diseases to which the natives had no immunity
decimated their populations, possibly by ninety-five percent in this area. By
the time English colonists arrived as settlers in the 1630s, the Paugussett
villages in the lower Housatonic River Valley were small and scattered. The
Paugussetts were not an aggressive people, and they did not resist the English
moving onto their land as the Pequots of southeastern Connecticut had done.
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The Great Swamp Fight
Ironically, a swamp along Fairfield’s coast became the setting for the final,
violent episode in the saga of the Pequot Indians, who fled their home territory
in Mystic (Missituck), Connecticut, after the English massacred hundreds of
women, children and older men by setting a village ablaze. The warriors were
preparing to defend a fortification at another location on that fateful night of
May 26, 1637. When they discovered the atrocity that had taken place in their
village, shock and disbelief overwhelmed them and they fled westward, away from
the territory of enemy Narragansetts and Mohegans, allies of the English.
Eventually the English found the Pequot survivors in an area inhabited by the
Sasqua Indians, now part of Fairfield. Among the English who fought in “The
Great Swamp Fight” in July of 1637 was Captain John Mason, the man responsible
for the massacre in Mystic, and the strong-willed, arrogant Roger Ludlow from
Windsor, Connecticut. Although the exact location of the battle is not known, it
took place in the vicinity of Southport. Eighty to one hundred Pequots, along
with their “hosts,” about two hundred Sasqua Indians, took refuge in the
swampland and were surrounded by the English. The Sasquas and the Pequot women
and children were allowed to leave the swamp, but the Pequot warriors remained,
and most or all were killed in the battle that followed. Sassacus, a Pequot
sachem (leader), and some of his followers had eluded the English, but met a
gruesome fate at the hands of the Mohawks in upstate New York. The surviving
Pequot women and children were captured and given to Indian allies of the
English and to the Massachusetts Bay Colony settlers to become their servants or
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English Settlement at Uncoway
In the fall of 1639, two years after the Great Swamp Fight with the Pequots,
Ludlow returned to the area, remembering its meadows and the cleared land that
had been cultivated by the Paugussett clans. Ludlow had received a commission
from the Connecticut General Court to establish a plantation near the Pequonnock
River on land that is now part of Bridgeport. When Ludlow arrived, he learned
that a disgruntled group of men from Wethersfield, who had recently joined the
New Haven Colony, planned to settle in nearby Uncoway. Unwilling to let this
desirable land fall into other hands, Ludlow disregarded the authority granted
by his commission, and proceeded to Uncoway with four other men.
Ludlow purchased land from the Pequonnock Indians stretching between the Sasqua
(Mill) and Pequonnock Rivers and roughly eight miles inland. The Indians agreed
to live on an eighty-acre tract west of the Housatonic River, formally
established as the Golden Hill Reservation in 1659. Other parcels of land in the
Fairfield area were reserved for them to farm and to hunt on, hence place
nicknames such as “Old Indian Field” that are still present as road names. Not
content with his sizable acquisition from the Pequonnocks, Ludlow continued to
purchase tracts all the way to the Norwalk River, extending twelve miles inland
in some areas. Despite exceeding the authority he had been granted, Ludlow was
only fined, and the settlement at “Uncoway” was permitted to remain.
The permanent settlement of Fairfield began in 1639 when Roger Ludlow laid out
four “squares” of land divided by five roadways. This area defined the center of
the new settlement, and remains today as the Historic Town Green with town
government buildings, churches, and the surrounding neighborhood. Home lots were
located within the four squares, while surrounding land was set aside for
pasture, meadow, and crop cultivation. In five years the town grew from nine
households to about twenty-four. New arrivals settled in the town center or
chose an area to the east that came to be known as Black Rock. However, people
could not freely choose to settle in Fairfield. Town Meeting participants
decided who was permitted to live here because the founders wanted a cohesive,
like-minded community. Those who were not approved were warned to leave the
town. Failure to obey the community’s rules could also result in expulsion from
As generations passed, families divided the land they had received as town
proprietors. New settlements sprang up further from the town center. Residents
petitioned to be recognized as separate parishes, because traveling to worship
in Fairfield center was a hardship; law required attendance. Stratfield, West
(Greens Farms), Greenfield Hill, and Redding were among the first newly formed
parishes in the 1720s and 1730s.
As the formation of new parishes and religious denominations continued through
the 18th century, Fairfield became a less homogenous community than its founders
would have found acceptable. These differences, as well as the physical distance
from Fairfield’s Town Meetings, set the stage for town separations. In 1767,
Redding became the first new town “carved” from Fairfield lands. The Norfield
and North Fairfield parishes below Redding became the town of Weston in 1787.
Half of Weston separated to become Easton in 1845. Westport was carved from both
Fairfield and Norwalk in 1835, and Black Rock was acquired by Bridgeport in
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Division of the Long Lots and
In the 1660s and 1670s, Fairfield began purchasing additional land from the
Indians, extending well into the area that is now Redding. (Fairfield’s northern
boundary was present-day Cross Highway in Redding.) This formalized expansion
was part of a colony-wide effort to gain control of land. When the British
monarchy was restored to power in 1660, New England colonists began to fear that
the mother country would renew its interest in the colonies and its land
resources. In 1671, Fairfield set aside a half-mile-wide swath of land running
approximately east-west and two miles north of the King’s Highway. A mile-wide
tract, intersecting the Half-Mile Common at its center, extended to the northern
boundary of Fairfield, today’s Cross Highway in Redding. Land on either side of
the Mile Common was divided into long, narrow parcels, which were distributed as
dividends to Fairfield proprietors. These “long lots” were about thirteen and a
half miles long and ranged in width from a mere fifty feet to 875 feet.
Residents who already had sizable land holdings typically received the widest
“long lots.” “Upright highways,” of which present-day Burr Street in Greenfield
Hill is an example, were created to provide access to the far ends of the long
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The Burning of Fairfield during
the American Revolution
On April 25, 1777, an army of British troops led by General William Tryon landed
at Compo Beach, an area now part of Westport. They marched inland through North
Fairfield (now Weston and Easton) and Redding to Danbury. Tryon launched the
raid to destroy military supplies stored in Danbury. Although Fairfield was not
touched, a second British invasion on July 8, 1779 proved catastrophic.
As the war dragged on, British commanders became increasingly irritated by the
rebel resistance in this area. Of particular annoyance were the privateering and
spying activities originating from Black Rock Harbor. In response, the British
decided to run a series of punitive raids against New Haven, Fairfield, and
Norwalk with the sole purpose of destroying rebel property.
On July 7, 1779, the people of Fairfield awoke to a warning from the fort at
Black Rock. A British fleet had been spotted and was anchoring off the coast.
With feelings of dread and uncertainty, residents prepared to defend the town.
Livestock was driven to safety. In haste, people gathered their possessions,
hiding their valuable silver in wells and stonewall crevices. Some loaded wagons
with household goods and food, and took refuge inland. Others stayed to defend
the town. A few remained in their homes, believing the British would not harm
them. No one predicted the extent of destruction that was about to occur, and
with it, the downfall of the town’s prosperity.
The British invasion came in late afternoon when the troops disembarked at
McKenzie’s Point (near the end of what is now South Pine Creek Road), and
marched along the beach, heading northeast. When they came to the lane that is
now Beach Road, they marched inland toward the center of the town. As they came
within range of cannons at Black Rock Fort, Isaac Jarvis, the fort’s commander,
ordered his men to fire on the troops. Local militia near the town center opened
fire with muskets. Undaunted by the attack, General Tryon and his troops
proceeded to set up headquarters in a home on Beach Road. The Fairfield men did
not give up. They successfully defended a makeshift fortification at Round Hill,
and tore up a strategic bridge crossing Ash Creek.
British troops under the command of General George Garth landed near Mill River
and marched over Sasco Hill toward Fairfield to join Tryon. Tryon’s intention to
march the combined forces to Black Rock Fort and attack from the rear had been
foiled by the destruction of the Ash Creek bridge. In retaliation he began
burning homes one by one. The terrifying scene became even more dramatic at
night; a lightning storm illuminated the sky, making the flames visible to
distant observers. But the greatest damage was inflicted on the following day as
the British left Fairfield. A rear guard of German mercenaries had been ordered
to cover the withdrawal. In the face of furious inhabitants, they set fire to
virtually all the buildings, including the churches and ministers’ homes, which
Tryon had given protection. Three men were bayoneted and another was shot.
Reverend Andrew Eliot, the Congregational Church minister, called the Jaegers
“the vilest [soldiers] ever let loose among men.”
Fairfield never fully recovered from the destruction. In 1789, ten years after
the fire and six years after the war ended, President George Washington stopped
at Penfield’s Sun Tavern in Fairfield. He observed, “The destructive evidences
of British cruelty are yet visible both in Norwalk and Fairfield; as there are
the chimneys of many burnt houses standing in them yet."
Fairfield’s stature as one of the most influential and prosperous towns in the
region diminished in the slow process of rebuilding. In the decades following
the war, the economic center of coastal Fairfield County shifted to Bridgeport
and its superior harbor.
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Patriots and Loyalists
During the Revolutionary War period political loyalties divided those people who
wished to remain subjects of Britain from those who believed fighting for
independence was necessary for the greater good. The consequences of supporting
either position were profound, and the resulting conflict sharply divided
communities, and even families. The American Revolution was, in many ways, a
Advocating independence from Britain could be dangerous, resulting in loss of
property, harassment, or worse. In 1777, Loyalists from Long Island burned
William Palmer’s Mill River home, and kidnapped his daughter. During the night
of May 2, 1779, Loyalist neighbors of Brigadier General Gold Selleck Silliman,
the head of Connecticut’s militia, assisted in a plot to kidnap him from his
home on Holland Hill in Fairfield. Silliman was taken by whaleboat to Long
Island where the British held him captive for almost a year. Connecticut
officials denied Silliman his salary during that time, contending that he was
not on duty when he was kidnapped.
Although history has cast Fairfield as an ardently patriotic town whose
residents endured loss and suffering at the hands of the British, Loyalist
families lived here as well, and they too suffered. The Reverend John Sayre,
Fairfield’s Anglican Church minister and an outspoken supporter of British rule,
pleaded with British commander General Tryon on behalf of his fellow citizens to
stop the burning of homes in July 1779. Sayre, who was also the town’s surgeon,
was indebted to patriot Fairfielders who had secured his release from Old
Newgate Prison two years earlier. Ironically, his church, located in the road
where Old Post Road and Old Field Road meet, was burned to the ground as the
troops departed Fairfield. The town had become a dangerous place for Loyalists,
and Sayre fled with Tryon. Other Loyalists had their property confiscated, and
at the close of the war, they were “evicted” from their homes and forced to
leave the country. Many departed from New York harbor on British ships sailing
to New Brunswick, Canada, where they began their lives anew on land grants from
the King of England.
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Slavery and Slave Owners in
During the 1600s, hereditary, race-based slavery slowly infiltrated New
England’s local economies. By the early 18th century, African-American slavery
had become an established institution. At the time of the American Revolution,
Connecticut was the largest slaveholding colony in New England, with slaves
comprising about three and a half percent of the population. In Fairfield, the
percentage ran higher: about six percent, or 260 of its 4455 residents. Most
slave owners in this area owned one or two people, whereas slave owners in parts
of southeastern Connecticut tended to own more. Only a handful of Fairfield
families owned five or more slaves.
Fairfield’s slave owners were mainly people of moderate wealth, in addition to
more prominent, wealthy citizens. Among them were several of the patriots who
supported the cause of liberty—Gold Selleck Silliman, Caleb Brewster, Thaddeus
Burr, and others—as well as Loyalists.
African-Americans, including some Fairfield residents, served in Connecticut
regiments during the Revolutionary War, and some earned freedom for their
service. But for most enslaved African-Americans, freedom was slow in coming.
Connecticut first began to address slavery in 1774 by banning the importation of
In 1780, two Fairfield slaves named Prince and Prime made a bold move to
petition Connecticut’s General Assembly for the emancipation of all slaves.
Other slaves had petitioned for their own freedom, but none before Prince and
Prime had argued that skin color should not oblige their race to serve another.
Although Fairfield’s Judge Jonathan Sturges supported the petition, it was
Finally, in 1783, a state law was passed that gradually ended slavery. Freedom
was granted to those born after March 1, 1784 when they reached age twenty-five.
However, there were qualifications. Only slaves in good health and less than
forty-six years old could be released, because towns did not want to support
elderly or disabled slaves cast off by their masters. The number of slaves
slowly dwindled, but slavery was not formally abolished by Connecticut until
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Sources of Prosperity:
Agriculture and Maritime Commerce
For nearly 300 years, until the early 20th century, agriculture was the major
source of Fairfield’s prosperity. In the 18th century, corn, rye, wheat,
potatoes, and flax were the main crops grown for export as well as local
consumption. Flax seed was in demand to make linseed oil, and was shipped to
Ireland where flax was grown to make fine linen cloth. Local farmers carted
their produce to merchants and shippers located along the wharves at Mill River
(now Southport) and Black Rock Harbor. Bartering was the common method of
exchange, and farmers often brought dairy and poultry products such as butter,
cheese, eggs, and sacks of feathers to trade for credit.
Fairfield’s coastal geography provided good harbors, an advantage that created
significant wealth in the 18th and 19th centuries through commerce and related
maritime industries. Shipbuilding became a profitable business at the deepwater
harbor in Black Rock in the early 18th century, with local shipyards known for
their fine craftsmanship. Black Rock merchants and shippers conducted a brisk
trade with vessels destined for the West Indies, Boston, and New York.
Livestock, grains, flax seed, preserved meats, dairy products, lumber, and
barrel staves were shipped from Fairfield. Return voyages from the West Indies
brought molasses, rum, sugar, and salt, while those from Europe brought luxury
goods. Newspapers advertised “newly arrived” items and the goods merchants would
accept in exchange. Access to these foreign imports set Fairfield apart from
many other towns in the region.
The harbor at Mill River (now Southport) was busy and crowded with smaller
vessels destined for New York and ports in southern states. In the mid-19th
century Fairfield farmers were raising about 41,250 bushels of globe onions per
year, and their output continued to grow. By the 1890s, the number of barrels
annually exported from Southport harbor had grown to an impressive 100,000.
Warehouses held the onions until ships were ready to sail. Market boats—sloops
and schooners—carried barrels of onions, carrots, and potatoes from Southport to
New York City from July to September. From October to May, their cargoes were
almost entirely onions.
Farmers from atop Mill Hill and Greenfield Hill kept an eye to the harbor for
market boats that would carry their produce. When one was spotted, word spread,
and lines of loaded carts and wagons soon appeared on the roads into Southport.
With the opening of western lands where soil was more easily cultivated,
agriculture declined in the region. In addition, in the late 1890s, cutworms
that could not be eradicated decimated the once-bountiful globe onions, and crop
production fell drastically. By the 20th century, mid-western farmers dominated
the production of grain crops, although dairy farming continued in New England.
In Fairfield, agricultural fairs and membership organizations that had once
supported farming and encouraged community pride began to die out. As the years
passed, land was valued more for its development potential than for growing
crops, and farmland was sold for homes, shopping centers and industry.
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The Arrival of the Railroad
In 1844, the Connecticut General Assembly approved the charter for the New York
and New Haven Railroad Company to begin construction of a rail line. Four years
later, in December of 1848, the first train came through Fairfield. Many of the
town’s residents did not greet this event with enthusiasm since it threatened to
change their quiet way of life.
In fact, the railroad’s impact was profound. Suddenly New York City was only a
two hour and ten minute ride away. Fairfield men could work in New York City and
return the same day if they chose. The new mobility also affected women, who
gained the freedom to visit friends and family in the city much more frequently.
People who had previously grumbled about the construction of a railroad soon saw
its advantages, including the economic benefits to the town.
The arrival of the railroad also initiated a change in Fairfield’s identity,
transforming its town center to a resort destination. Well-to-do city dwellers
found respite in the peaceful setting with its ocean breezes, and some built
lavish summer homes in the town. Others stayed at the fashionable and imposing
new hotel, Fairfield House, situated near the town green. Construction of the
hotel in 1848, the town’s first, coincided with the new railroad. The hotel
stood on the northeast corner of Main Street (Old Post Road) and Center Street
(Beach Road), and was said to be the largest of its kind in the state, boasting
more than one hundred rooms. It also featured a ballroom, dining room, and
spacious verandas where summer visitors could enjoy the setting and fresh air.
In 1889 the name was changed to Hotel St. Marc’s, and a large annex was
constructed, the only portion that remains today on the property.
Steamboat service from Bridgeport and Norwalk to New York also brought many
visitors but was gradually reduced, as train travel, with its convenient local
stops, became the norm.
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New Neighbors: Immigrants of the 19th
and Early 20th Centuries
The “melting pot” of cultural traditions and religions that distinguish American
life began in earnest in the mid-1800s, as successive waves of European
immigrants arrived on America’s shores. The chance for a better future attracted
farmers and peasants whose lives were tied to poverty by feudal land ownership,
or battered by political upheavals. In Fairfield, the declining population of
founders’ descendants was infused with newcomers from Ireland, Sweden, Italy,
and Eastern Europe who saw in the town their land of opportunity.
Years of potato crop failures in Ireland began the trend in the 1840s and 1850s,
forcing thousands of families to choose between emigration or starvation. Irish
immigrants took employment here as laborers and domestics, sometimes displacing
African-Americans. But the transition was not easy. Prejudice against Irish
Catholics was widespread and persistent, especially in New England with its
Puritan heritage. Despite this barrier, Fairfield’s Irish population grew to
thirteen percent by 1860.
As industrial centers multiplied and expanded in the late 19th century,
immigrants supplied the increasing demand for cheap labor. Thousands of recent
arrivals found their way to Bridgeport’s burgeoning factories. People of similar
ethnic backgrounds typically clustered in neighborhoods, which were given the
nicknames “Little Italy” and “Little Poland.” These neighborhoods provided a
sense of community, as well as cultural and linguistic continuity, important for
those who found factory work alien to their agrarian background.
Some eventually purchased land to cultivate in Fairfield, and later built homes
on their land. In the early 20th century, new, culturally distinct neighborhoods
began to emerge in Fairfield. Land that had once been considered undesirable for
farming--on Fairfield’s east side and in areas west of the town center, where
marshes had been drained--provided that opportunity, especially among Hungarian
immigrants. The Tunxis Hill area became home to people from Poland, Russia,
Slovakia, Hungary, and Sweden, and it continues to be identified with the
immigrant population that settled that area although ethnic businesses have now
largely disappeared. Many of the street names reflect Hungarian heritage, while
local churches like Fairfield’s Magyar Reformed Church and St. Emery’s Roman
Catholic Church, maintain Hungarian cultural traditions. The large population of
Italian immigrants who came to Bridgeport also contributed to Fairfield’s
cultural mix, although they did not settle in any one particular neighborhood.
Fairfield’s Jewish population was quite small until after World War II, when
many chose the Fairfield Woods and Stratfield neighborhoods on Fairfield’s east
side as their home.
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Intolerable traffic congestion on Connecticut’s roadways is not a recent
phenomenon. In the 1920s, as the popularity of automobiles increased, existing
roads proved inadequate and frustrating to drivers. Connecticut resisted the
idea of multiple-lane highways, even as neighboring Westchester County in New
York State began building a modern parkway system in the 1920s. The potential
for new highways to attract out-of-state sightseers was viewed as an intrusion
on quiet New England.
As traffic problems worsened, a controlled-access highway seemed to be the only
solution. In the early 1930s, plans for a parkway, designed with distinctive
bridges and landscaping, was approved. In 1934, construction began on the
Merritt Parkway as a federal Works Project Administration (W.P.A.) project. The
first section of the “Queen of Parkways,” between Greenwich and Norwalk, opened
in July of 1938. The remaining stretch of the thirty-seven-mile route, including
Fairfield’s hard-won “no exit zone” through Greenfield Hill, opened on September
2, 1940. Each of the original thirty-four bridges spanning the parkway was
individually designed, contributing to its unique character, and making it an
appealing route for travelers.
Commercial traffic was prohibited from the parkway, however, and truck accidents
on Route 1 remained a serious problem. In the early 1950s, a Shore Line Thruway
was proposed by the Connecticut Highway Department, but was opposed by advocates
of an inland route less vulnerable to foreign attack. During the Cold War years,
the threat of attack to Connecticut’s shoreline infrastructure and towns was
perceived to be real. Despite the fears, the Shore Line route won, and
construction of the Connecticut Turnpike was underway in 1956.
Construction of the Connecticut Turnpike formed a major link in the country’s
East Coast artery, Interstate 95. Fairfielders reported immediate improvements
on the Post Road as trucks began using the Connecticut Turnpike. But the
convenience of the nation’s new highway system came with a high price tag. In
many urban areas and towns, older neighborhoods were bisected or completely
razed in the name of “progress.” Some homes in the Mill Plain area were moved to
new sites but others fell victim to the wrecking ball. The greatest losses
occurred on the eastern side of Fairfield in the Holland Hill and lower Tunxis
Hill neighborhoods settled by Hungarians, Poles, and Swedes. These neighborhoods
were fractured by the expressway route, which drastically altered residents’
daily routines and, ultimately, the cultural cohesiveness.
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American Settlements and Contact with English Colonists
| The Great Swamp Fight | English
Settlement at Uncoway | Division of the Long Lots and
Commons | The Burning of Fairfield during the American
Revolution | Patriots and Loyalists |
Slavery and Slave Owners in Fairfield |
Sources of Prosperity: Agriculture and Maritime Commerce
| The Arrival of the Railroad | New
Neighbors: Immigrants of the 19th and Early 20th Centuries |
is courtesy of
Fairfield Museum and History Center,
370 Beach Road, Fairfield, CT 06824