Red Mill on the Five Mile River

In 1989, Peter and Marilyn Carroll Biggins and family purchased a house newly-built by St. John Associates on an acre of land in Darien, Connecticut, at 230 Old Kings Highway North, on the east side of the old mill run for the Red Mill at Five Mile River. This was the first house ever built on this site. The only previous structures were a gristmill (the Red Mill) and sawmill on the west side of the mill run between 1692 and 1908. The street was originally part of the old Boston Post Road between New York and Boston. Darien was called Middlesex, part of Stamford, until 1820.

Mile 48. 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.

From the 1867 Map of Darien, showing the Grist and Saw Mills at the intersection of the Five Mile River and the Old Post Road, now Old Kings Highway North.

230 Old Kings Highway North, Darien, Connecticut. March 2006.

Map showing how Canaan Parish was created from Stamford and Norwalk in 1731.Source: Portrait of New Canaan: The History of a Connecticut Town, by Mary Louise King, 1981, p. 26.

Walking Down the Five Mile River

In 1997, Peter had an annual physical and the doctor suggested he exercise regularly. As a result, Peter started walking four miles a day down to Long Island Sound. His normal route is down Raymond Street and Five Mile River Road to the mail boxes near the end of Five Mile River Road, and back. Initially, the walk took an hour. After 20 years, however, it was up to an hour and 15 minutes.

Walking the same route around sunrise day after day, you get to learn something about the route and know some of the residents along the way. And you wonder about the part of the river you don't see. In 2020, he decided to start this research on the river.

You also learn that the most common birdsong on the last two miles of the river is that of the tufted titmouse (Baeolophous bicolor), official bird of PetersPioneers. The song is a whistled peter-peter-peter-pete.

Nearby Rivers

The Five Mile River is one of a number of small coastal rivers of varying length that flow under the Post Road (US-1), the New Haven Railroad, the Merritt Parkway (CT-15), and the Connecticut Turnpike (I-95) into Long Island Sound in southwest Connecticut. Rivers within fives miles east and west are:

• Rippowam (Mill) River, 17 miles in New Canaan and Stamford ending in Stamford Harbor. Rolling Mill; Saw Mill and Wire Mill north of Cedar Heights Road, off Wire Mill Road
• Noroton River, 9.5 miles in New Canaan and along the Darien/Stamford border, ending in the Cove. Cove Mill on Stamford side of Holly Pond and Cove Harbor; Liquorice Mill, north of I-95; Grist Mill and Saw Mill north of Jelliff Mill Road in New Canaan
• Goodwives River, 6 miles in Darien. Grist Mill, at Rings End. Joined by Stony Brook
• Five Mile River, 12 miles in New York, New Canaan, Norwalk, and the Norwalk/Darien border, ending in Rowayton Harbor. Fourteen old mills and factories
• Norwalk River, 23 miles in Ridgefield, Brannchville, Georgetown, Wilton, and Norwalk, ending in Norwalk Harbor. Multiple mills in Georgetown. Winnipauk Mills in Norwalk. Joined by Silvermine River north of Broad Street at Deering Pond
• Saugatuck River, 24 miles from Sugar Hollow Pond in southwest Danbury to Redding, Weston, and Westport.

What's in a Name?

Mary Louise King says that the Five Mile River was so-named because of its distance from the Saugatuck River (Portrait of New Canaan: The History of a Connecticut Town,, 1981, p. 8). The Five Mile River is five miles west of the Saugatuck River, measured along Long Island Sound. But, it is also five miles east of the Rippowam (Mill) River.

Frank Raymond dispels the myth that the original name of the river was Five Mill River. He says the river was referred to as the Five Mill River in 1656, but there were no mills on the river at that time. It was obviously a misspelling (Rowayton on the Half Shell, 1990, p. 16).

Five Mile River

The Five Mile River watershed consists of a network of small streams and wetlands buffered by meadows and undeveloped forest. Drinking water is drawn from the New Canaan Reservoir, which marks the downstream extent of the headwater region. Farther downstream, the river passes through residential neighborhoods and dense commercial centers in New Canaan, Norwalk, and Darien. The river forms the border between Darien and Norwalk south of the Post Road.

The headwaters of the Five Mile River are about 300 yards north of the Connecticut/New York border (Puddin Hill Road) and 40 yards west of Smith Ridge Road, in the Vista section of Lewisboro, New York.

There are 20 crossings of the Five Mile River:

• I-95, the longest north-south interstae highway, running from Maine to Florida
• the Merritt Parkway, and expressway limited to cars
• U.S. 1, a federal highway running from maine to Florida
• four Connecticut state highways
• a commuter railroad
• the old Post Road
• various smaller streets

The estuary, or mouth, of the river is at Long Island Sound, about 12 miles from the headwaters in New York State. You can easily see the North Shore of Long Island, about seven miles away. In the estuary, oyster farming was a major industry, peaking in the early 20th century. There were two dramatic, rocky projections - one on Butler's Island, and the other slightly upriver, formerly known as the Loading Rock. It was used for loading cargo sloops in the 18th and 19th centuries. The Loading Rock as well as other local coastal scenes were favorites of John Frederick Kensett (1816-1872). The Metropolitan Museum holds several paintings of the Five Mile River in its Kensett collection. See Marian Castelli's Loading Rock.

Anne Morrow Lindbergh lived at the end of Five Mile River Road until 1999.

Below is a table showing points of interest on the Five Mile River, using Google Maps and 1867 maps of New Canaan, Norwalk, and Darien. Twenty crossings (grey) were found along the way on present-day maps. Fourteen old mills and factories (bold) were drawing water power from the river on the 1867 maps. Elevation is 565 feet above sea level at the headwaters, down to sea level at Long Islad Sound (Topozone).

Headwaters

1867 New Canaan Map. The headwaters of the Five Mile River are about 300 yards north of the Connecticut/New York border (present-day Puddin Hill Road) and 40 yards west of present-day Smith Ridge Road, in the Vista section of Lewisboro, New York. To the left of the river is present-day W Road and Lake Woods Road. To the right of the river is Smith Ridge Road.

2020 Google Map. The headwaters of the Five Mile River are about 300 yards north of the Connecticut/New York border (present-day Puddin Hill Road) and 40 yards west of present-day Smith Ridge Road, in the Vista section of Lewisboro, New York. To the left of the river is present-day W Road and Lake Woods Road. To the right of the river is Smith Ridge Road.

1867 New Canaan Map. The headwaters of the Five Mile River are about 300 yards north of the Connecticut/New York border (present-day Puddin Hill Road) and 40 yards west of present-day Smith Ridge Road, in the Vista section of Lewisboro, New York. To the left of the river is present-day Oenoke Ridge Road, south of J. Selleck, and Lake Woods Road. To the right of the river is Smith Ridge Road. The crossroads from north top south are Michigan Road, Summersweet Lane in Pleasant Valley, and present-day Country Club Road. The Summersweet Lane crossing was replace by the New Canaan Reservoir.

Mills in New Canaan

1867 New Canaan Map. Two mills on the Five Mile River in New Canaan 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. Present-day Forest Street is west of the river. River Street is east.

1867 New Canaan Map. Three mills on the Five Mile River in New Canaan, The cross street is present-day East Avenue. To the north is a saw mill. To the south is a saw mill and a grist mill on present-day Mill Pond.

Mills in West Norwalk

1867 Norwlk Map. Saw mill & axe helve factory, sash & blind factory and saw and feed mills, on the Five Mile River in Norwalk, south of present-day Old Rock Lane and north of present-day Fillow Street.

Old Red Mill in Darien

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).

1894 picture of the Old Red Mill, Darien, Conn. From the Norwalk side of the Five Mile River, the gravel Country Road (then called Old Kings Highway) crosses an a-frame bridge over the river and winds past the grist mill up the hill toward Raymond Street. There is an early utility pole at the far left. To the left of the mill (across the mill run) is a the miller's house, with a picket fence. Between the utility pole and the bridge is the mill run flowing back into the Five Mile River.

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.

Mills at Chasmer's Pond in 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 Five Mile River on the present-day Tokeneke Road at White Bridge.

Falls on the Five Mile River north of White Bridge. 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

1867 Norwalk Map. The area south of West Norwalk and north of Rowayton is called Middle Five Mile River. Flax Hill Road is called the Old Post Road. The new Post Road is called Turn Pike Road.

1867 Norwalk Map. Rowayton is called South Five Mile River. The Five Mile River is on the left. Wilson Cove is on the right.

Rowayton

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 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. Contentment Island, incluiding 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.

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. There are 9 oystermen, 6 farmers, 4 house carpenters, 3 ship carpenters, 1 shipwright, 2 clerks, and 1 Indian agent 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 on the southern half of Five Mile River Road viewed from southeast of the turnaround. High tide. Circa 1900. Source: Michael Cattano.

"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). From the collection of the Amon Carter Museum, Fort Worth, Texas. 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.

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 be seen in the background. High tide.

Google Map of the Mouth of the Five Mile River, 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 Based Plan

Map of of the Five Mile River. Source: Five Mile River Watershed Based Plan, The South Western Regional Planning Agency, 2012.