Prehistoric and Native America

Archaeological evidence places indigenous habitation in the New England area just over 10,000 years ago. In the post-glacial environment, forests were primarily conifers of spruce and pine with indications of deciduous oak tree. Large mammals and small game, including fish, mollusks and waterfowl from streams and Long Island Sound, were hunted by nomadic bands. Foraging for edible plants, berries and nuts was an important supplement to their diet.

Throughout the Archaic Period (10,000-700BC), indigenous people lived in increasingly hardwood forests of oak, beech, hemlock, hickory, walnut and chestnut. Game became smaller in size. There is evidence of handmade ground stone tools for processing and chopping, as well as ubiquitous stone spear points for hunting. Seasonal resources were maximized through transient hunting and foraging while living in or under rock shelters. By the end of this period, there is archaeological evidence of simple frame dwellings covered in skin or bark, ceremonial burial and animal domestication.

The Woodland Period (700BC-1633AD) initiated the production of pottery, enabling increased food production and storage. Agriculture now provided a steady food supply that supported a larger, native population but imposed sedentism. Stone tools and projectile points become more varied and sophisticated. Specific stylistic types and decoration emerged that indicate their point of origin and the possibility of water and overland trade.

Increased exploration and trade in the sixteenth century began to transform Connecticut’s indigenous peoples, settlement patterns, and language dispersal. An influx of Dutch, French and British fur traders also brought disease that decimated the tribes of coastal New England. It has been estimated that less than 10% of the native peoples who had once populated the area survived when Europeans began their settlement.

By the time of widespread European contact in the early 1600s, the Algonquian tradition characterized Fairfield County. The Westport area was further defined as the Paugussett/Pootatuck group, though there were many dialects and sub-groups such as the Aspetuck, Compaw, Maxumux, Pequonnock, Sasqua, Saugatuck and Uncowa.

An 1889 published history of Fairfield describes the remaining native settlements that were believed to exist at the time of English settlement: the Pequonnock occupied the Housatonic River valley east of Westport. The Uncawa occupied territory west of the Pequonnock to Southport. The Sasqua occupied lands about the Great Swamp and Sasco Creek. The Maxumux occupied the lands west of Sasco Creek to Compo, extending inland to the Aspectuck River. The Compaw occupied the lands between Compo and the Saugatuck River. West of the Saugatuck were the Norwalk people. North, along the Aspetuck River, were the Aspetuck.

Colonial Settlement

The first English settlers of Connecticut were from the Massachusetts Bay Colony, founding the Connecticut River Valley towns of Windsor, Wethersfield, and Hartford in 1635. In 1636, the General Court of Massachusetts appointed the first governing body of what would become the Connecticut Colony. One of the first acts of this new government was to declare war on the Pequots of southeastern Connecticut.

While centered a hundred miles east in Mystic, the Pequot were the most powerful of the Connecticut tribes and controlled virtually all of Long Island Sound. The Pequot were reputed to have had a history of aggression against other tribes, and in particular the Mohegan. They were also the most resistant tribe to English settlement in Connecticut. Their massacre in 1637 by a militia under the leadership of the new Massachusetts Bay Colony, with the support of the Mohegan and Narragansett tribes, is significant because it marks the first time in English North America that a native population was removed by conquest. Westport shares in this history because it was in the Great Swamp along Sasco Creek, which today forms the town’s eastern border with Fairfield, that the last of the fugitive Pequot, under the leadership of the Sachems Sassacus and Mononotto, were hunted down. Those not killed were sold into slavery to Bermuda or dispersed among tribes friendly to the English. This battle, which is known as the Great Swamp Fight, took place in July of 1637. It is said that 180 Pequot were killed. Sassacus and Mononotto escaped to New York, though Sassacus was later killed by the Mohawk.

Fairfield County was thus opened to English settlement following the conquest of the Pequot tribe. In 1639, just two years after the Pequot War, the deputy governor of the newly established Connecticut Colony, Roger Ludlow, led the establishment of the first settlement in Fairfield County on a large tract of land purchased from the Pequonnock, setting aside reservations for various clans or sub-tribes. The tract of land so purchased was known originally as Uncoway, after the Uncawa tribe, and included what today forms the towns of Fairfield, Redding, Weston, Easton, part of Bridgeport, and most of Westport. In 1645, the settlement was formally named Fairfield as the fourth town established in the Connecticut Colony. The Pequonnock retained a settlement on Golden Hill, which in 1659 was formally recognized as the Golden Hill Reservation.

For its first two centuries the entire area east of the Saugatuck River, in what is now Westport, was part of the Town of Fairfield. That part west of the Saugatuck River was part of Norwalk. The first settlement of greater Fairfield occurred in 1639 where the Fairfield Town Green now stands. In 1648, five “Bankside Farmers” settled in what would become in time the Town of Westport. Known simply as Bankside, this settlement was located on elevated shorelands between Sasco and New Creeks, in the Frost Point vicinity and near Green’s Farms.

In 1671, to secure its territory, the greater township of Fairfield set aside a half mile wide commons running east and west, about two miles north of today’s Kings Highway. Centrally intersecting this was another commons, one mile wide, running north and south. “Long lots” granted to homesteaders were laid out parallel to the Mile Commons. In 1703, a schoolhouse was erected just north of Bankside, in what is now known as Green’s Farms. In 1711, the first meeting house in the Westport portion of Fairfield was erected just west of New Creek, near Machamux Rock at the foot of what is now Morningside Drive South. A cemetery was also laid out near where Green’s Farm Road crosses Muddy Creek. In 1737, a new Green’s Farms Meeting House was erected opposite the cemetery. In the theocratic tradition of the day, the meeting house was for both church and state – the center of the newly established West Parish of Fairfield.

By the 1720s this farming community had prospered, broadening its settlement to encompass land from the tidewater of Compo Cove and the fresh headwaters of Muddy Brook, into the northerly interior of town, to the so-called Long Lots. Compo Neck, which stretches westerly from the Cove to the mouth of the Saugatuck River, was also settled. By 1732, the West Parish had three school districts which reflected the settlement pattern to date – Green’s Farms, Long Lots and Compo.

Early European settlement of New York and New England had to this point been largely restricted to the coast which permitted easy access by water. However, following the conquest and submission of the Native American population, interior portions of New England were opened for settlement. This also encouraged greater inland transportation between cities. In 1672, Kings Highway was laid out through what is now Westport as part of a great undertaking connecting New York City and Boston by overland road. Homesteads, roadway inns, and shops were soon erected along this highway, thus beginning the second phase of settlement of Westport lands.

This expanded pattern of settlement also included lands that were part of the Town of Norwalk, west of the Saugatuck River, that later became part of Westport. As there were no bridges across the river, the new highway followed the old Pequot Trail across a natural ford just north of today’s Westport Center, and by 1700 settlement of this upriver area was beginning as well. Eventually, even more remote interior areas of town were settled, with such farming hamlets as Coleytown in the northernmost part of today’s Westport, and Taylortown on Old Hill. Weston was also settled as Europeans moved inland.

Kings Highway was further improved during the 1750s, under the guidance of Benjamin Franklin, as the Boston Post Road – the primary corridor connecting the northeast colonies’ major urban centers. In 1761, a Kings Highway bridge was erected over the Saugatuck River. The first wharves had also been erected by this time on the Saugatuck, on what was still the Norwalk bank at Edge Hill. By the time of the American Revolution, the town’s farming community, with access both by land and sea, was prospering as it marketed its produce to neighboring communities and even abroad.

Throughout the colonial settlement era, slavery was part of the local economy. While much smaller in scale than in the South, slavery in Connecticut did not start to wane until just before the Revolution. At its peak, it is said that slavery accounted for 6% of the population of Fairfield County. In 1774, Connecticut banned the importation of slaves. During the Revolution, some slaves earned their freedom by fighting for the patriots. In 1783, the state passed legislation to phase out slavery, granting freedom to slaves upon the age of 25. In 1845, slavery was formally abolished altogether.

Revolutionary War

The town would see action during the Revolutionary War, as this agrarian market redirected itself to the cause of supplying American troops. To disrupt these patriotic efforts, a British sea force, under General William Tryon, landed at Compo Point on April 25, 1777, and marched northward to pillage military stores stockpiled at Danbury. Three days later, as the British returned to their ships, another battle took place at Compo Hill.

Two years later, on July 7, 1779, Tryon and his British troops, this time with German mercenaries as well, returned in a further attempt to disrupt the supply lines to the Continental Army. Landing at McKenzie’s Point and marching over Sasco Hill, the first exchange of gunfire was near Black Rock in Fairfield. A simultaneous invasion led by the British General George Garth landed near Mill River in what is today Southport and marched to join Tryon. Encountering resistance, homes were set afire by the British. As the British returned to their ships the next day, almost every structure they passed was burned. In that part of Fairfield that is now Westport, the old West Parish Meeting House of Green’s Farms, fifteen houses, and eleven barns were burned. The economic impact on all of what was then greater Fairfield was substantial and led to the relocation of much of the county’s commerce to Bridgeport.

Early Republic

With the emergence of American sea trade after the Revolution, a descendant of the original Jesup family of Green’s Farms, Ebenezer Jesup, undertook a major maritime development of the Saugatuck River, constructing a wharf near its navigable headwaters. In 1811, to promote his new port, Jesup arranged for the construction of a new highway by his riverfront facility, including a new carriage bridge across the Saugatuck River. By diverging from the Kings Highway, Jesup impacted on the future of Westport in two ways. First, Kings Highway was left as a side road, thereby preserving its colonial heritage to this day. Second, he began the development of what would become Westport Center on the Saugatuck River.

The year 1818 saw a fundamental change in state politics, as power transferred from the established Congregational oligarchy to a new republicanism founded on Jeffersonian ideals. Church and state were finally independent and dissident groups associated with the maritime communities of southern New England began to forge a new political power. The maritime community of the Saugatuck River was part of this movement, identifying more with the disestablishmentarian attitudes of the New York and Rhode Island merchant classes than of the old puritanical Congregationalism of Connecticut’s landed gentry.

In 1835, in large part due to this new political awareness, Westport was incorporated as a separate town encompassing both sides of the Saugatuck, though it excluded for these same political reasons the old West Parish of Green’s Farms. A portion of Weston also joined the new Town of Westport. The name “Westport” was selected to reflect the port’s new prominence in western Connecticut.

While remaining part of Fairfield, the farming interests of the Green’s Farms and Long Lots districts were integrally intertwined with the port operations of Westport and Southport as the export market for farm produce continued to expand. Within seven years, the Green’s Farms and Long Lots districts overcame their philosophical differences with Westport and elected to merge with the new town.

Mid-Nineteenth Century

The ports of the Saugatuck and Mill Rivers shipped grain and agricultural produce to as far away as Texas and the West Indies, in return for sugar, molasses, cotton, and lumber. While the development of superior farmlands in newly opened lands of the American interior meant the end to many New England farms, local farming survived and even thrived by supplying the nearby booming New York City metropolitan area with fresh dairy and agricultural produce. Moreover, Westport’s farmlands were remarkably suited for the farming of onions, and the town became famous for its many varieties. During the Civil War, Westport was the major supplier of onions to the Union troops. This era was also significant for the "Underground Railroad" which is reputed to have operated via the river and Old Hill in the northwest part of town to Weston and beyond.

Westport’s farms thus prospered, with wealthy homesteads built throughout the nineteenth century. However, in the 1890s, a cutworm infestation all but wiped-out onion farming in Westport, and agriculture largely succumbed to the much larger operations of the American Midwest. The one areas of agriculture that survived were dairy and the cultivation of corn and hay as feed of dairy cows. Oystering was another prosperous activity with numerous dedicated oyster grounds along the town’s Long Island Sound shoreline.

Meanwhile, Westport Center had become the town's financial and business center. The bridge that Jessup had built there in 1811 remained the main route over the Saugatuck River until 1873 and was thus a primary force in consolidating commercial interests in Westport Center during the era of the river port economy. From Westport Center to Compo Point, the new merchant class erected stately houses along the shores of the river. These were intermixed with the wharves, ship and coal yards and factories of the maritime community. Willowbrook Cemetery was laid out during this time following the romantic landscape traditions of the mid- nineteenth century. In 1882, the original Staples High School was founded. A horse trolley connected Westport Center along Riverside Avenue to a railroad depot down river. A steamboat wharf was located at National Hall.

Upriver from Westport Center, along the non-navigable waters of the Saugatuck, emerged the town’s first true industrial concerns. The Saugatuck Manufacturing Company was erected there in 1814, utilizing the waterpower of the river. In time, this district became known as Richmondville.

After the Civil War, another mill village emerged towards the mouth of the river, near a railroad bridge built in 1858 and a carriage bridge built in 1873, the first bridges over the Saugatuck Rover to be built south of Westport Center. Inhabited by Irish and later Italian immigrants, this village usurped the name Saugatuck, which had earlier been applied to Westport Center. Though there were several other small factories located along Riverside Avenue, the emergence of coal power and the railroad concentrated factories in larger cities and Westport never became a major center of manufacturing.

Westport’s prominent families of the time were engaged mostly in commerce and shipping, and during the economic boom of the post-Civil War 1870s, many of Westport’s fine Italianate styled houses were erected. However, the turn of the twentieth century saw the general demise of smaller seaports as shipping became consolidated in larger cities. Without the railroad, Westport Center had seen little in the way of industrialization. Instead, its energy was redirected to the professional and service sectors of what was soon to become an exclusive exurban resort community.

Turn of the Twentieth Century

While the railroad, which had been constructed along the Westport shoreline in 1858, never brought industrialization to town, it would have an important impact on it. By the 1880s, commuter lines gave the wealthy elite of New York City access to the amenities of Westport’s countryside and Long Island Sound shoreline. Thus began the era of great exurban estates and summer shoreline resort community. Salt marsh farms became waterfront estates, particularly along Beachside Avenue. New estates arose amongst the older sea captains’ houses on the Saugatuck. Interior farms became vast country estates, with a number in the northernmost part of town.

The late nineteenth century country estate of Morris Ketchum off Cross Highway encompassed 500 acres, laid out in the naturalistic manner of Frederick Law Olmstead, the foremost American landscape architect of the nineteenth century. The 180-acre Longshore estate was built by George Laurence on Long Island Sound during the 1880s. During the 1920s, Laurence’s estate was taken over by the Longshore Country Club, in which capacity it continues to this day. The Beachside Inn was erected about the same time overlooking Phipps’ Beach near Green’s Farms Railroad Station and became a popular resort for wealthy city dwellers. E. T. Bedford erected his estate on Beachside Avenue at the turn of the twentieth century, his extensive grounds including a racetrack. Bedford would become a major benefactor of the Town of Westport, financing school buildings, a fire station and the YMCA building during the first part of the twentieth century. In 1908, the Westport Public Library was established.

While Beachside Avenue had become an exclusive residential community by 1920, a more modest cottage resort community was constructed overlooking Long Island Sound at Compo Beach. A bathing pavilion was erected there in 1919, and in 1927 an expansive beach compound was completed with dining and dance halls, bath houses and lifeguard facilities. Soon a yacht basin was dredged. A similar compound of bungalows soon emerged in the Compo/Owenoke area. The Miramar, a luxurious 1920s speakeasy, was erected on Hillspoint Road in 1919, but no longer stands. This is also the era that saw Westport become one of the premier artists’ communities in the United States. The Westport Country Playhouse, for instance, has been active since 1930.

The integrity of the historic and natural environment of early twentieth century Westport fostered the emergence of what characterizes much of Westport’s architecture today. At the time, older houses were recognized as historic and were renovated into picturesque country estates. New estates attempted to reflect the gentrified agrarian traditions of old Westport. The popularity in Westport of what has become known as the Colonial Revival style is reflective of the great interest that was shown a century ago in New England’s rural and colonial architectural heritage.

Mid-Twentieth Century

By 1920, with the emergence of the automobile as an integral part of the upper-class mainstream, Westport began to see its first true suburban development. During 1924, the state rebuilt Boston Post Road through town as part of the northeast’s first true automobile highway – US Route 1. The construction of the Merritt Parkway, part of the Depression-era WPA effort, through the northern portion of town consolidated Westport’s evolution from a town of exurban country estates and summer cottages to one of a fashionable suburban community. Completed in 1940, the Merritt Parkway, with its individually designed bridges, has been listed on the National Register of Historic Places.

By the time the Connecticut Turnpike (now I-95) was cut through southern Westport in 1956, most of Westport’s open lands had been subdivided. Today we recognize this period of early suburbanization to be part of the historic fabric of the town.

Today

Westport’s historic fabric of colonial homesteads, Victorian maritime community, country estates, seaside cottages, and comfortable suburbs remains largely intact. However, in just the past few years, a number of historic residences have been demolished to make way for larger houses, with the Town of Westport having one of the highest, if not the highest, rates of teardowns in the state. Nonetheless, identifiable areas that maintain a distinct sense of history and place, and that are worthy of protection, are found throughout the Town of Westport. Among these areas are the following:

• Bankside
• Beachside
• Burying Hill Beach
• Charcoal Hill
• Coleytown
• Compo
• East Bank
• Edge Hill
• Frost Point
• Green’s Farms
• Long Lots
• Mill Cove
• Newtown Turnpike
• Old Hill
• Old Mill Beach
• Poplar Plains
• Roseville
• Saugatuck
• Saugatuck Shores
• Taylortown
• West Bank
• Westport Center

While the environment we seek to preserve retains much of its historic integrity, there are threats. In particular, there is the pressure of speculative commercial interests capitalizing on the prosperity that the tradition of environmental respect has brought to Westport. Unchecked, development which is not compatible with Westport’s long commitment to the natural and architectural environment can only compromise the very zeitgeist of the community.

Fortunately, the town has adopted significant measures through its Historic Design Districts and Local Historic Districts, historic preservation zoning initiatives, and demolition delay ordinance, to promote more appropriate development in the future. With this handbook, the Historic District Commission continues its progress towards a comprehensive town wide historic preservation plan – a plan which can preserve Westport’s heritage for future generations.