Indians

The Indians inhabiting the Five Mile River area were a physically large people and included the generally peaceful Siwanoy tribe. The Siwanoy lived in small villages of bark-covered wigwams. They made wampum from clam and oyster shells found in abundance at the estuary of the river, and fashioned arrowheads and other stone implements for a relatively simple life devoted to hunting, fishing, and the farming of corn.

At the estuary on the west side of the Five Mile River is Butler's Island, where one may still find occasional arrowheads and see the remains of a Siwanoy pothole, a large rock scooped out in the center and used to grind corn and other seeds. The rock is directly beside what must have been a giant oak. It is believed that a stone was hung from a branch on the tree at just the right height to permit the stone and pothole to work like a pestle and mortar.

Huge buried piles of oyster and clam shells indicate a probably major Siwanoy encampment just to the west of the Five Mile River in the Tokeneke area of woodlands, meadows, coves, and tidewater streams. Chief Tokeneke is the name and mark of a sachem, of chief, of a people who were here before the earliest white settlement. His name appears on some original land deeds in the state archives.

The peaceful Siwanoy ("The South People") were surrounded by less pleasant neighbors. To the east were the warlike Pequots and to the northwest the savage Mohawks. For protection the Siwanoy joined other small tribes throughout Westchester in the "Wappinger Confederacy," a league which more or less controlled the land lying between the Saugatuck and Hudson Rivers. It is thought that the Five Mile River was used by the Siwanoy as a guide in their travels north to attend those council meetings with their brother clans and to hunt.

Colonists

Early settlers were attracted to land near the Five Mile River because of the good fishing. Each settler received a houselot, woodland, and pasture. Common lands were reserved for the grazing of cattle. But early colonial writers refer to the shores of the Five Mile River as being infested with smugglers and squatters who were in constant conflict with the Indians and the early white settlers.

The Five Mile River was, in fact, a boundary line in the earliest local agreements signed by the English colonists and the Indians. In 1640 a deed was signed to land extending from the Five Mile River on the east to the Mianus River on the west and from Long Island Sound to about 10 miles north. The buyer was Captain Nathaniel Turner, an agent for the New Haven Colony. The sellers were Ponus, Sagamore of the Toquams, and his brother Wascussee, Sagamore of the Shippan ("shore where the sea begins"). The mark of the Ponus, a medicine man whose name translates "he who uses herbs," was a lightning streak. The mark of the Wascussee was a bow and arrow. The price of the transaction was 12 coats, 12 hoes, 12 hatchets, 12 mirrors, 12 knives, 2 kettles, and 4 fathoms of white wampum.

In 1640(?) the Five Mile River was the eastern boundary of the Norwalk land purchased from the Indians by Roger Ludlow and Captain Daniel Patrick. But these lands were not settled until 1650.

In 1645 another Indian sale completed the purchase of what is now Darien. Piamikin, sagamore of "Roaton," sold much of the land between the Five Mile and Goodwives rivers--including Long Neck point, Great Island, Salem Straits, and Delafield Woods--to Andrew Ward and Richard law of Stamford for 4 coats and some tobacco. This land was purchased because the original colony of Stamford and Noroton had grown from 28 families in 1638 to 59 by the end of 1642. In the sales agreement Piamikin stipulated that the English must agree not to build houses on the land, for he feared the English hogs would run in the Indian corn fields and ruin the crops.

Boundary disputes on the river were common. Because Piamikin had sold some of the land bordering the Five Mile River to both Stamford and Norwalk, there were many bitter arguments over the right of Norwalk men to cut hay west of the river.

In 1685 the land at Runkinheag (now called Tokeneke) was subdivided into lots of several acres apiece and assigned to men who were living in Stamford center. The brothers John and Jonathon Bates were among the first to be granted land in this area.

As new generations grew up in Stamford, fathers dipped into their land holdings and turned over lots on the outskirts of town to their sons and grandsons. One such property near the Five Mile River is at 148 Old Kings Highway North at the corner of East Trail. The land records of 1705 show that John Bates gave his son Jonathon a wedding present of that location on the "Country Road" and included an unfinished house on the property.

Rivers are often used for transportation, but there is no evidence that the Five Mile River was used extensively in this fashion. Rather, a road from new Canaan to the mouth of the river called "the road to the Five Mile River Landing," was used to transport produce. Its purpose was to reach port by the best route then available, and it followed the line of the river fairly closely.

The river did, however, become a shipping center for the area, and it could be said that the Five Mile River was the chief reason for the existence of Rowayton. Soon after Rowayton was settled in the 1780s, a flourishing commerce brew up. Farmers as far away as New Canaan brought there produce to be loaded on sailing packets and carried to New York to be sold or traded for goods.

The river also had a series of mills. There were two grist mills on the Darien side of the river: one at White Bridge and another on a brook that runs into Scott's Cove. There was also a grist mill on Chasmars Pond and a mill farther up the river near the bridge on Kings Highway.

In New Canaan, there were seven mills. John Brotherhood's parking lot is the site of William Boult's 1761 cider mill. The 1782 estate inventory of Peter Smith indicates a cider mill on his 300 acres north of Michigan Pond. On Summer Street Weed's flour mill was in full blast about 1824, and Benedict Wood had a large grist mill not far away. In 1848 Anthony Comstock replaced an old saw mill on Mud (or Mill) Pond with a new mill.

But the most information is known (from a history of New Canaan 1801-1901) about the saw, grist, and cider mill on Mill Pond owned by Justus Hoyt, the blind miller of New Canaan.

Hoyt's mill was the old Millport Mill on what was known as Hanford's Millpath (now Millport Avenue), north of the present Lakeview Cemetery (which was deeded as a cemetery by Hoyt), and replaced the first mill on Mill Pond. The new mill was built by Levi Hanford in 1757. He sold the mill and pond to Cook St. John, who later sold it in 1852 to Justus Hoyt, who lost his eyesight in an accident when he was 9 years old.

Justus Hoyt took his son-in-law Lewis St. John Olmsted into partnership. Olmsted then took Justus Fitch Hoyt on as a partner to his thriving flour mill until Olmsted sold his grist and saw mill to him on July 11, 1876. Although the mill has long since disappeared, the spillways and foundations are still visible.

King's Highway. King's Highway North, the road where we park to walk on the Traendly flood plain, was the first "Colonial Road" and united New York and Boston. In 1679 it was recognized as an indispensable artery connecting the coastal communities when the General Assembly ordered that "the country road or King's highway connecting the plantations be cleared to one rod wide. Then in 1703 an order was issued under the Act of the Provinces relating to highways to survey and lay out a continuous road to follow the Indian trails and the cartways already in existence. For many years after, this improved road was still little more than a cartway full of rocks, holes,and stumps.

In 1722 a stagecoach schedule was established between Boston and new York once very two weeks. This schedule was discontinued during the Revolution when British forces occupied new York. But by 1787 commerce had grown, and the New York-Boston stage made three trips a week.

Among the many famous men who travelled this road were Paul Revere, John Hancock, and General Lafayette. John Adams drove along this spot in 1774 on his way to the First Continental Congress. He was accompanied by the other delegates from Massachusetts: Samuel Adams, Robert Paine, and Thomas Cushing.

George Washington passed this way three times. He was interested in the stone fences along the way and remarked upon the many droves of beef cattle and flocks of sheep he saw being driven along this area to the New York market.

Benjamin Franklin, our first postmaster general, travelled the road measuring each mile of the improved road with s special wheel, which was attached to his wagon. At the end of every mile he drove into the ground a wooden stake which was later replaced by a solid milestone.

Modern Man

In the early part of the 19th century, Rowayton became the center of a flourishing oyster industry. For the first time oysters were "planted" off the mouth of the Five Mile River. In the "planting" process oysters were added to the natural beds during the spawning season, thus increasing the number of grown oysters that would eventually be harvested.

Rowayton also kept up with the growing needs of the shipping industry by becoming the home of several shipbuilding yards. Eventually, however, with the advent of the railroad, the sailing packets slowly disappeared from the scene; and the railroad became the main means of transportation for the many industries (such as the carriage and felt hat factories) which had, along with the grist mills, developed around the Five Mile River.

Commercial and private fishing today is very active in Rowayton Harbor and in the estuary of the Five Mile River. Oystering is still carried on. Heavy steel plates are dragged along the harbor floor, and the oysters are taken on timed trips to the greater tidal areas near the Norwalk Islands and near Bridgeport and New Haven.

Clamming too is a very important trade. Clams are taken out of the Norwalk Islands, where the stronger tidal currents allow a clam to cleanse itself of all pollutants in 3 rainless days. (Heavy rains seem to wash dangerous products into the water.)

Menhaden (or bunker) are very important bait fish caught in the river, where the fearsome and ravenous bluefish (which require more oxygen and deeper water) have chased them. Cods (Tommy cods or frost fish), flounder, crabs, lobsters, and eels are also caught.

Upriver is mostly residential, with some industrial (the notable examples are the Holiday Inn, Old MacDonald's Farm, and the New Canaan Sewage Treatment Plant).

New Canaan Reservoir between Oenoke Ridge Road and Summersweet Lane. Made of concrete, 470 feet long, 44 feet high, completed in 1898. 2.1 miles from the heafwaters of the Five Mile River. See: Dam Safety Inspection. Owned by South Norwalk Electric and Water (SNEW).

New Canaan

1867 New Canaan Map. On the left side of the map is the central area of New Canaan. East-west streets are Elm Street, Cherry Street, and Maple Street. North-south streets are Park Street, South Avenue, and Main Street. Main Street north angles northwest, then become Oenoke Ridge road as it heads north. Main Street south parallels the Five Mile River and becomes White Oak Shade Road and, eventually, West Norwalk Road. At the top of the map are two mills on the Five Mile River, at the foot of present-day Parade Hill Road. A saw mill was north of the Smith Ridge Road bridge. A grist mill was to the south of that bridge. Forest Street is west of the river. River Street is to the east. Locust Avenue runs northeast from Main Street and crosses the Five Mile River, after which it becomes Brushy Ridge Road. Summer Street runs south from Locust Avenue, crosses East Avenue, and ends at lakeview Avenue. Today, Brook Street comes off Summer Street between Locust Street and East Avenue and crosses the Five Mile River. East Avenue runs east from Main Street and crosses the Five Mile River. To the north of East Avenue is a saw mill. To the south of East Avenue and the present-day Mill Pond, are a saw mill and a grist mill. Alongside the Mill Pond is Millport Avenue. Crossing Millport is Lakeview Avenue. Running north from Lakeview is Summer Street.

Border Between New Canaan and West Norwalk

Where the Five Mile River crosses the border between New Canaan and West Norwalk, there is an old mill pond and mill run that Mary Gai has pointed out. A dam and mill pond can be seen from Meeting Grove Lane. A driveway goes over the dam. There is a mill run from the mill pond that goes under Meeting Grove Lane, runs south along the Lane, goes back under the Lane just before Old Rock Lanem and enters the river. There is no sign of a mill structure along the mill run. There is a sluice gate built into the dam.

Mill pond on Five Mile River looking southwesterly toward the dam/driveway on the border between New Canaan and West Norwalk. The mill run is on the left.

Close up of driveway, dam, and sluice gate.

Close up of sluice gate valve, looking northwesterly into mill pond.

Five Mile River looking north toward the dam/driveway on the border between New Canaan and West Norwalk. There is a ledge to the left.

Northeasterly close-up of the the dam/driveway taken from the ledge. The sluice is just to the right of the ledge.

This mill pond and mill are not shown on the 1867 maps of either New Canaan or Norwalk, so they must have been built after 1867.

West Norwalk

1867 Norwalk Map. Two miles of the Five Mile River run through West Norwalk, crossed by Old Rock Lane at the top of the map, Fillow Street in the middle, and West Cedar Street at the bottom. The upper left corner is New canaan. The lower left corner is Darien. Along the left side of the map is West Norwalk Road. South of Old Rock Lane are a saw mill & axe helve factory. Farther south are a sash & blind factory just south of a pond now called Millard Pond. See: Dam Safety Inspection To the left of the sash & blind factory is Stephen Mather Road proceeding west from West Norwalk Road into Darien. Still farther south are a saw mill and feed mill on a mill pond just north of Fillow Street and just south of a pond now called Florsheim Pond. See: Dam Safety Inspection. (See photo below.) Old Rock Lane ends at Weed Avenue, which runs from the top of the map to Fillow Street. In the center of the map, Fillow Street meets Richards Avenue, which runs down the center of the map and crosses West Cedar Street at the bottom of the map. The forked tributary in the middle left of the map is the Holy Ghost Fathers Brook, which enters the Five Mile River to the west of what is now St. John Cemetery. In the center of the map, Scribner Avenue proceeding south east from Richards Avenue, passing the end of West Cedar Street, and crossing the Post Road in the bottom right corner of the map. West Cedar Street runs across the bottom of the map from West Norwalk Road to Scribner Avenue. At the bottom of the map, east of Richards, is Keeler Avenue proceeding south from West Cedar Street. The forked river in the bottom right corner is Keeler's Brook, with flows into the File Mile River.

Florsheim Pond Dam at Fillow Sreet

Florsheim Pond dam, from Fillow Street.

Old McDonald's Farm

Old McDonald's Farm was on the north side of the Post Road at the Darien-Norwalk town line, where the Post Road crosses the Five Mile River. It had a petting zoo, a bakery, a restaurant, and an amusement park from 1955 to 1979.

Covered bridge across the Five Mile River at Old McDonald's Farm.

Sign for the Five Mile River on Connecticut Avenue (the Post Road) in Norwalk

Old Post Road and Old Red Mill

From 1789 Colles atlas, Map 4, page 7, showing the Old Post Road, now Old Kings Highway North, the Red Mill ( Grist *), the Five Mile River (southbound squiggly arrow), and 48 miles from Federal Hall. Present day streets: Richards Avenue to the north (A to Canaan) and Rowayton Avenue and Raymond Street to the south. George Washington is known to have crossed the Five Mile River when he traveled on the Old Post Road in Middlesex (Darien) in 1756, 1775-76, and 1789, as Colonel, General, and President. See: Red Mill on the Old Post Road

1867 Darien Map. Saw and grist mills on the Five Mile River in the Five Mile School Ditrict of Darien, on the present-day Old Kings Highway North (Old Post Road). From the 1870 census for Darien, page 26: John L. Reed, 56, farmer Matilda Reed, 47, keeping house, born in England Mary, 19, at school Howard, 15, at school Richard Bates. 59 farmer Hannah Bates, 70, keeping house Sally Roberts, 71, keeping house Charles N. Roberts, 31, farmer, born in New York Sarah Richards, 90 Rosa Schullen, 35, domestic servant, born in New York Henry Weeks, 62, millwright, born in new York Lewis L. Reed, 49, farmer Phebe M. Reed, 38, keeping house, born in New York Frances A. Reed, 15, at school

1867 Norwalk Map. Five Mile River, on the present-day Flax Hill Road (Old Post Road).

Sign at Brookside Cemetery on Richards Avenue, south of the Old Post Road, showing the Red Mill, the 1789 Colles map of the Old Post Road, and information about the Reverend Moses Mather (1719-1806, who is buried in the cemetery. Source: Norwalk Historical Society. See larger image.

1894 photo of the Old Red Mill, enhanced by the Norwalk Historival Society and displayed at Brookside Cemetery on Rowayton Avenue. Shot southwesterly from the Norwalk side of the Five Mile River bridge. In the foreground, the non-macadamized old Post Road (called the Farm Road in the 1900 census) crosses an A-frame bridge over the river. The road winds past the grist mill up the hill toward Raymond Street. The mill building is center right. The mill run and wheel are under the roof on the right side of the building. The mill is three stories high. At the top is a hoist that would lift grain to the top floor. Two utility poles can be seen at the far left. The first municipal electric plant in Connecticut began operating in the City of South Norwalk in 1892. Between the utility pole and the bridge is the mill run flowing back into the Five Mile River. To the left of the mill is a house built in 1880 that is today at 222 Old Kings Highway North. A long white fence parallels the road toward Raymond Street, probably starting in front of the house. See Unenhanced photo

Below is a 1934 aerial photo provided by Greg Smith who grew up at 11 Richards Avenue. Old Kings Highway North/Flax Hill Road (Old Post Road) snakes across the middle. The Five Mile River bridge is in the center. Old Kings Highway North is to the left of the bridge. The first house south of the bridge is 222 Old Kings Highway North. Flax Hill Road is to the right. Shadybrook Lane angles up and left from Flax Hill Road at the bridge. Raymond Street is on the lower left, Richards Avenue is on the upper right. Traendly rose greenhouses are at bottom right. The Post Road is at the very top left. Getner Farms are upper right. There was no I-95.

1934 aerial photo.

2022 map of appriximately the same area as the above 1934 aerial photo.

Down river photo of the back of 230 Old Kings Highway North by Gina Nichols on a cold February 4, 2023.

Up river photo of brave Mallards by Gina Nichols on a cold February 4, 2023.

Down river photo by Gina Nichols on a cold February 4, 2023.

Canada geese with six goslings by the mill pond of the Old Red Mill, spring 2022. Photo by Anthony Zangrillo.

Egret on the mill pond of the Old Red Mill, summer 2020. Photo by Anthony Zangrillo.	Canada geese family on the mill pond of the Old Red Mill, spring 2020. Photo by Anthony Zangrillo.
	Canada geese family on the mill pond of the Old Red Mill, spring 2021. Photo by Anthony Zangrillo.
Wild turkey overlooking the mill pond of the Old Red Mill, with photos of grist mill and saw mill on the wall at 230 Old Kings Highway North, Darien, October 2020. Photo by Peter Biggins.
Snapping turtle that climbed up from the river to the Zangrillo back yard. "He must have been 40-50lbs; took a lot to carry him down and put him back in the river." June 2021. Photo by Anthony Zangrillo.
Five inches of snow on the morning of February 28, 2023--the only snow that amounted to anything that winter.
Up river view of maple blossoms, April 12, 2023. In the background can be seen the remains of the dam for the Old Red Mill.
Painting by Sister Mary Benzing, SSJ.

Map from The River Book. View of the Five Mile River looking south from Old Kings Highway North. Source: The River Book, A Study Guide to the River and Its Environment, The Junior League of Stamford-Norwalk, Third Edition, 1977, p. 51.

Traendly Flood Plains

The Traendly Flood Plains property was transferred to the Darien Land Trust in 1977. It is 13.22 acres of river flood plains feeding Five Mile River. It has a population of diverse wetland species and is a refuge for many types of wild life. In the 1980s and 1990s it was used extensively in the spring and fall for river study programs for Darien and Norwalk 4th graders and other groups.

2003 Map. Traendly Flood Plains of the Darien Land Trust. Source: Darien Land Trust.

Chasmer's Pond in Darien/Rowayton

1867 Norwalk Map. Feed mill and sash, door & blind factory on the Five Mile River in South Five Mile River section of Norwalk, on the present-day Rowayton Avenue, south of the New Haven Railroad.

New York, New Haven and Hartford Railroad crossing the Five Mile River in the 1880s. The falls at Chasmer's pond dam are visible under the bridge. Source: postcard at the Norwalk Public Library.

White Bridge

1867 Darien Map. Grist mill on the the Five Mile River at "the top of the salt." Between Raymond Street and the river. North of Tokeneke Road at White Bridge.

Falls over the grist mill dam on the Five Mile River at "the top of the salt." White Bridge in the foreground. Source: postcard at the Norwalk Public Library.

Open-sided car of the Norwalk Tramway Line that ran between Darien and Norwalk, crossing the Five Mile River at White Bridge from 1893 to 1933. Source: The Story of Darien, Connecticut, by Kenneth M. Reiss, 2009, p. 192.

Middle and South Five Mile River in Norwalk (Rowayton)

1867 Norwalk Map. The area south of West Norwalk and north of Rowayton is called Middle Five Mile River. Turn Pike Road is the new Post Road. Old Post Road is Flax Hill Road. The road to the north is Richards Avenue. The road to the south is Rowayton Avenue. "Old Cem." is Brookside/Five Mile River Cemetery (Rev. Moses Mather 1719-1896), just west of Keelers Brook.

1867 Norwalk Map. Rowayton is called South Five Mile River. The Five Mile River harbor on the left was central to shipping businesses from the early 1800s through the early 20th century. South of the shipping businesses were homes of many oystermen and boat builders. Roton Point is at the bottom center. In the late 1880s, this popular picnic spot began to expand its entertainment offerings aided by a trolley system that brought people to the site every 20 minutes and, eventually, large steamships that would ferry thousands of people to the park every day. In Wilson Cove on the right is Tavern Island, owned by the Norwalk Oystermans Association in 1867. In the 1920s, Tavern Island was the home of Billy Rose, a famous entertainer and bootlegger. Lillian Hellman completed her Academy Award-nominated screenplay The Little Foxes while living on Tavern Island in 1939.

The Five Mile River harbor looking north with sailboats and steamboats at docks. Lobster pots are piled in sailboats and on the pier. There are boys in rowboat at right. Source: postcard at the Norwalk Public Library.

WPA mural "Packet Day at Five Mile River" by George Avison, 1937. Restored circa 1986. Located at the Rowayton Library. Packet sloop "Chief" loading produce for the new York market in the Five Mile River at Rowayton. Source: Rowayton Historical Society.

Five Mile River Landing Historic District. The Five Mile River Landing Historic District is a residential neighborhood of small to medium-sized domestic and public buildings dating from the late 18th century through the early 20th century. It is the residential remnant of a larger 19th century maritime village. The district is located on the eastern bank of the Five Mile River in the village of Rowayton, in the southwestern part of the City of Norwalk. It includes Rowayton Avenue from the northern edge of Rowayton's business district to Jo's Barn Way. The district also includes Pennoyer Street. In addition to relying on the geographic boundary of the Five Mile River, the district's boundaries were drawn from the historic development patterns of the area - as early maps demonstrate, the 19th-century residential corridor along the Five Mile River did not extend beyond these streets in this area.

With its proximity to the river, the district is low lying. The high point is located at the eastern end of Pennoyer Street, which rises from Rowayton Avenue next to the river to the top of a small ridge. The streets are open and relatively free of trees, adding to the sense of a coastal setting. The buildings are located on a mix of small and medium sized lots with most of them located quite close to the street and to each other. The one exception to this is the Seeley-Dibble-Pinkney House at 177 Rowayton Avenue, which sits closer to the river than the road on a large lot relatively far away from its neighbors.

The Five Mile River Landing Historic District exemplifies a typical 19th century residential district, with a mix of styles from throughout the period. The buildings are wooden, mixing both timber- and balloon frames, and range in height from 1.5 to 3.5 stories. They are clad in clapboards, shingles, stucco, or a mix of these materials. In addition to the domestic buildings and their outbuildings, the proposed district also includes one church, a boathouse, a carriage house, and a building constructed as a hotel.

The buildings also reflect a variety of styles. While many of the buildings in the district are vernacular, several are good examples of specific styles. The Federal style is represented by the side-entry Seeley Dibble Pinkney house (c. 1820) at 177 Rowayton Avenue. A simple example of the Greek Revival can be found at 186 Rowayton Avenue, the Captain William Sammis House (c. 1842). 12 Pennoyer, the Baptist Parsonage (c. 1872), was constructed in the Second Empire style. 8 and 14 Pennoyer Street, the James E. Stevens House (c. 1872) and the Corvino L. Ogden House (c. 1888) respectively, were built in the Queen Anne style. The Methodist Church (c. 1868) was originally constructed as a simple, clapboarded building with an arched, tripartite window above the door and a small rose window in the gable. In 1908 it was thoroughly renovated into a Late Gothic Revival-style building.

In addition to the buildings, the district includes two open spaces. Near the southern end of the district a town park (established in 1966) includes two contributing buildings at its northern end and the contributing site of a former shipyard at its southern end. In 1901, a traffic island was created at the intersection of Rowayton Avenue and Wilson Avenue, near the southern boundary of the district, for a monument topped by a naval artillery piece to commemorate Rowayton's Civil War dead. The original inscription reads as follows:

Memorial Gun
Reminding us of the Heroic Deeds of Our
Soldiers and Sailors of the Republic in the War
Of the Rebellion for the Preservation of the Union
Erected 1901
From U.S.S. Tallapossa

Plaques were subsequently added to the base of the monument to honor the citizens of Rowayton who died during World War I and World War II. (See: The Historical Marker Database)

There are 27 buildings, 1 site, and 1 object in the district (exclusive of sheds and other minor outbuildings). 19 (66%) contribute to the district. Among the non-contributing structures are seven garages, two modern houses and a small boathouse.

Map of the Five Mile River Landing Historic District. Source: National Register of Historic Places, National Park Service.

The Five Mile River Landing Historic District demonstrates the development pattern of the domestic portion of a Connecticut riverine maritime village as it grew from an area of scattered farm houses to an oystering village and seasonal vacation spot and, finally, into a year round suburb. Since its founding, Rowayton has looked to the Five Mile River and Long Island Sound for sustenance. The area's earliest settlers turned to the river and Long Island Sound for fish, salt hay, and transportation. As the area developed, the importance of coastal trade and shipbuilding expanded in Rowayton. This was followed by notable growth in the oystering industry in the mid-19th century as well as the beginning of the area's time as a vacation destination. By the beginning of the 20th century oystering began to decline and vacationers started to build more permanent houses, changing the area's character from seasonal to suburban. (Elements of all of these phases of the village's development can still be seen in the historic district.) Throughout this time, the driving force behind all of these developments was the area's shoreline location. This pattern - moving from subsistence agriculture and fishing to trade and commercial fishing, or in the case of Rowayton aquaculture, to tourism and finally, to a suburb - is a common one along the Connecticut coastline. The district focuses on the area's domestic buildings built during the 19th century, when it enjoyed its greatest growth, although there are examples of buildings from each phase of the area's development.^ Taken together the district represents a significant and distinguishable historic entity.

The district was first divided for settlement in 1705; 8 acres in the district were given to John Raymond. A local historian suggests that the properties were most likely granted prior to this point but not officially recorded until 1705. By the end of the 18th century the area was populated with farmers and watermen; the Raymonds appear to have been farmers.

The oystering business reached its peak in the quarter century between 1885 and 1910. Coinciding with this boom in oystering was the advent of streetcar service to Rowayton in 1890. This amenity, along with the already extant trains and the soon to be prevalent car, prepared Rowayton for the final chapter in its history. In the early years of the 20th century the villagers began to look away from the water for their livelihood and began commuting to jobs in South Norwalk and beyond.

By the end of this period the character of the area around the intersection of Pennoyer Street and Rowayton Avenue was set, with a few additions it would remain a reminder of fin de siecle Rowayton.

Five Mile River Road in Darien

The start of Five Mile River Road from Tokeneke Road. The Five Mile River curves off to the left. Old Farm Rod branches off center left. From photo taken in 1890. Source: The Story of Darien, Connecticut, by Kenneth M. Reiss, 2009, p. 30.

1867 Darien Map. Five Mile River Road, just west of the Five Mile River. The Tokeneke school district was then the Five Mile River. Contentment Island, including the house of Vincent Colyer on the highest point on the island, where John Frederick Kensett lived and painted scenes across the mouth of the Five Mile River.

1870 Census.Following is information from The U.S. Census of 1870 that matches up with houses on part of the 1867 map of Darien shown on the left, which includes Five Mile River Road and Contentment Island. Shown is name, age, occupation, value of real estate, and state where the person was born. Not shown below are spouses and non-working children. Occupation: 9 oysterman, 6 farmer, 4 house carpenter, 3 ship carpenter, 2 clerk, 1 shipwright, 1 Indian agent. State of birth: 13 Connecticut, 11 New York, 2 New Hampshire, 1 Maine. 1870 U.S. Census, Darien, Connecticut, page 32 Stephen Raymonf, 61, farmer, $10,000, Connecticut 1870 U.S. Census, Darien, Connecticut, pages 29-31 Mary Selleck, 78, $8,000, Connecticut William S. Selleck, 55, farmer, Connecticut Alanson Williamson, 55, ship carpenter, $2,000, New York Satt Williamson, 21, house carpenter, New York Andreus Millspaugh, 31, house carpenter, New York Benjamin Williamson, 18, clerk, New York Stephen Ferris, 87, farmer, $12,000, Connecticut John Ferris, 65, farmer, Connecticut Wm. S. Walmsley, 48, farmer, $8,000, Connecticut Stephen E. Walmsley, 26, farmer, Connecticut Hiram G. Taylor, 45, oysterman, Connecticut Hiram B. Taylor, 22, oysterman, $2,000, Connecticut Olever Cook, 45, oysterman, $3,500, Connecticut Stephen Cook, 19, oysterman, Connecticut Edward Lowndes, 52, oysterman, $2,000, New York Charles Lowndes, 45, oysterman, $5,000, New York Wm. B. Delemater, 70, shipwright, $1,600, New York Augustus Thomes, 52, clerk or agent, $2,500, Maine Gardner F. Thomes, 22, house carpenter, Conneticut William Hoyt, 41, house carpenter, $2000, Conneticut Frank Williamson, 37, oysterman, $2,000, New York Henry T. Cole, 62, ship carpenter, $2,000, New Hampshire Dexter K. Cole, 31, oysterman, $2,000, New York John H. Cole, 29, oysterman, New Hampshire Hickson Williamson, 64, ship carpenter, $3,000, New York 1870 U.S. Census, Darien, Connecticut, page 47 Vincent Colyer, 45, Indian agent, $4,000, New York

Houses at 120, 118, 116, and 114 Five Mile River Road viewed from southeast of the turnaround. High tide. The building on the far left is a barn. Circa 1900. Source: Michael Cattano.

In December 2020, J. Chris Hall wrote: "I just recently happened upon your article about the Five Mile River and found it quite fascinating. I grew up on the river, first at 118 Five Mile River Road (1951-1958) and later at 110 Five Mile River Road (1959-1969). My mental mind set was that the river ended at the White Bridge. This was, no doubt, because this was where navigation ceased. The only exception to my myopic vision up stream from the bridge was the unique residential property that was on the Darien side of the river but was only accessible via a ramshackle private bridge from Rowayton [ed. note: Carolyn Place, no longer ramshacle]. Our school bus would cross into Rowayton to pick up students. Your narrative and pictures are great. The picture that you date to about 1900 was of interest to me as it included what is now 118 Five Mile River Road. (Second house from the left) The barn shown in the picture could be the one we used for making wooden rafts to 'explore' amongst the mountains of reeds which used to cover the west side of the river. Thanks for making my day!"

"Five Mile River, Rowayton, 1920" by the noted marine artist John Stobart. Oil on canvas, 1986. This view looks southeast from Darien towards Rowayton and Long Island Sound. Oyster boats are plying their trade, catching the tide on a late morning in the early fall. This image appears on the inside front and back covers of Rowayton on the Half Shell by Frank Raymond, 1990. See Kensington-Stobart Gallery.

Sunrise over Five Mile River harbor. High tide. November 2019. Photo by Gayle Campbell.

Paintings by by John Frederick Kensett

"Old Pine, Darien, Connecticut” by John Frederick Kensett (1816-1872). From the collection of the Metropolitan Museum of Art, New York, New York. Painted from the southeast shore near the artist’s studio on Contentment Island. Visible in the painting is the profile of Roton Point, with Pine Point beyond. Kensett built a studio on the high southeastern bluff of Contentment Island, overlooking the Fish Islands and Long Island Sound; it was a short walk from the house. See John Kensett and the Connecticut Shore.

"Study on Long Island Sound near Darien, CT” by John Frederick Kensett (1816-1872). In the collection of the Amon Carter Museum, Fort Worth, Texas, but sold in 2003. Painted from a lower elevation, on the southern shore of Contenment Island, looking toward the low sandy spit at the western end of Sheffield Island. See John Kensett and the Connecticut Shore.

In October 2020, Dennis Dixon wrote: "I'm 67 and I grew up on Tinywood Road (in the "backcountry"/"wilderness" of Darien), and spent many happy hours at the Tokeneke Beach Club and the Wee Burn Beach Club, and I have always loved going over File Mile River and down through Rowayton. Reading your wonderful blog about Five Mile River (and then playing with Google Maps) felt great.

"The reason I hit your blog is artist John Kensett, and his "Study on Long Island Sound near Darien, CT" painting. It is no longer in the collection of the Amon Carter Museum of American Art, Fort Worth, TX - they deaccessioned (sold) it through Christie's in 2003. That is one reason why I travel around and visit museums - to see this stuff (Hudson River School artists, Winslow Homer) before they decide to either sell them or lock them up for good.

"Keep up the good work, and Stay Safe!"

Aerial Views of the Mouth of the Five Mile River

Northwesterly aerial photo of Roton Point Park (1880-1941) on Long Island Sound in the foreground and the Five Mile River harbor in the background. The southern half of Five Mile River Road runs along the far right side of the river. High tide. Circa 1930. Source: Michael Cattano.

Southerly drone photo of the Five Mile River and the southern half of Five Mile River Road. The Greens Ledge Light and Long Island can barely be seen in the background. High tide.

Loading Rock

In August 2020, Michael Cattano provided notes of Marian Castelli, Darien Town Historian, about Loading Rock, which was once a small center of commerce/port for Oyster Harvesting:

“To the east of Contentment Island, at Five Mile River, there were two dramatic, rocky projections - one at the mouth of the river, on Butler's Island (now joined to Contentment Island by a causeway), and the other slightly upriver, formerly known as the Loading Rock, because it was used for loading cargo sloops in the 18th and 19th centuries.”The Loading Rock has been a local landmark for centuries: “At Five Mile River, oyster sloops took on their cargoes at Loading Rock, a huge boulder, part of which still remains a landmark on the west side of the river.” From Connecticut Place Names by Arthur Hughes and Morse S. Allen, 1988, p. 109.

“Loading Rock: A large rock on the west bank of Five Mile River near 125 Five Mile River Road, used as landing by packet books” [which sailed up the river from the 1700s through the late 1800s]. From Rowayton of the Half-Shell by Frank Raymond, 1991.

Greens Ledge Light and Long Island

Google map of Greens Ledge Light, built in 1902. One mile south of the mouth of the Five Mile River and 5.6 miles north of Eatons Neck Point on the North Shore of Long Island.

Greens Ledge Light. Legend has it that Greens Ledge was named after a pirate Green, who sailed with the infamous Captain Kidd. When Green was captured by authorities of the day, he was reportedly executed and his body fastened to the ledge in chains as a dire warning to others thinking of entering the buccaneering trade. Years later, a lighthouse would be established on the ledge as a warning to vessels seeking to enter Norwalk Harbor. See Lighthousefriends.

Five Mile River Watershed

Once home to thriving populations of wild and native trout - indicator species that require the coldest, cleanest water - the Five Mile River has become degraded over time due to land use changes and climate change. See: Trout Unlimited.

The Five Mile River Watershed encompasses approximately 7,995 acres of land. The watershed includes the areas around the streams & brooks that feed the Five Mile River (tributaries), such as Holy Ghost Fathers' Brook and Keelers Brook. Source: City of Norwalk

Map of of the Five Mile River. Source: Five Mile River Watershed Based Plan, The South Western Regional Planning Agency, May 21, 2012. See also: FINAL Five Mile River Watershed Summary, September, 2012, and Five Mile River Watershed Report Card, Summer, 2012.