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. 

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 slaves. 

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 the town.

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 1870.

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 lots.

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.

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 civil war. 

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.

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 slaves. 

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 denied.

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 1848.

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.

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.

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.

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

by artist and historian William D. Lee 

Please click on the thumbnail image to view a larger version of the mural. 

The Mural of the Purchase of Fairfield,  painted by artist and historian William D. Lee, was dedicated in a ceremony on Monday, January 28, 2002.  The mural is located in the front foyer of Sullivan Independence Hall.

Mr Lee, Municipal Historian Emeritus, has described his mural as follows:                                                                                                                                                

"Roger Ludlow was born in England in 1590.  He was educated at Oxford, and then went on to complete his studies in law.  He was truly a puritan and an intellectual leader of the period.  He also became an active member of the Massachusetts Bay Company.  The lure of the new land in America was a challenging and adventurous attraction to Ludlow.  He came from England to the New World in 1630 on a ship that he owned.

Within the following ten years, he became one of the most ambitious colonizers in New England.  Although many people were in attendance at this Purchase Agreement ceremony, this mural focuses on Ludlow and the Chief of a small clan of the Pequonnock Tribe located in Unquowa (Fairfield).  The Pequonnocks were part of the Paugussett nation in this part of Connecticut.  There are varied interpretations of Ludlow and Native American tribal leaders in the 17th century.

Ludlow, dressed in typical 17th century Puritan attire, is offering much valued glass Trading Beads as a portion of the Agreement.  The Native Americans perceived glass as a valuable and supernatural substance.  Their preferences in color were red and blue.

Included in the ceremony, the Tribal Chief would implant a twig into the soil.  This symbolized conveying the land and all that the land sustained to the English.  The Tribal Chief also exhibits a new and prized English wool blanket draped across his shoulders.

It was common for both men and women to paint their faces and stain their bodies red, as the Trial Chief demonstrates.  This was the reason early explorers called Native Americans "Red-Men".  Likewise, feathers were worn in various arrangements and distinguished outstanding leaders of the tribe.

The figures in the background represent four prominent settlers that accompanied Ludlow. They are Thomas Newton, Edward Jessop, Thomas Staples and Edmund Strickland.

Similar land purchasing agreements in this vicinity included the trade of blankets, hoes, knives, axes, kettles and mirrors.  The original detailed trading documents for Fairfield were destroyed and burned by the British during the American Revolution in 1779.  In the Harbor is a typical ship of the period and to the rear of Ludlow is a mountain laurel, now the Connecticut State Flower."

The image of the mural is courtesy of Jim Gilleran.