Disambiguation: This page is about the Five Mile River in southwestern Connecticut, not the the Five Mile River in northeastern Connecticut.

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. The house is 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) on the west side of the mill run and a sawmill on the east side of the mill run. 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.

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.

Source: Part of Map of Connecticut, showing the Five Mile River, nearby rivers, grist and saw mills, and the old Post Road. Fl. is for fluss, German for river. Rowdens River is Noroton River. Middlesex is Darien. Old Well is South Norwalk. Map Legend. Designed by Daniel Friedrich Sotzmann based on maps by Blodget, Carey, and Ristow collected by Christoph Daniel Ebeling in Hamburg, Germany. Published by Carl Ernest Bohn in Berlin, Germany, 1796.

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.

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.

The 1789 Map of the Old Post Road by Christopher Colles includes mile markers on the Post Road starting at the southern tip of Manhattan. The Five Mile River is at mile marker 48. The Five Mile River is east of the Rippowam River by 6.2 miles, the Noroton River by 4.0 miles, the Goodwives River by 1.0 miles. It is west of the Norwalk River by 3.2 miles, the Saugatuck River by 7.6 miles.

What's in a Name?

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

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).

On Google Maps and the U.S. Geological Survey, the name is Fivemile River.

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, including :

• Puddin Hill Road, the New York/Connecticut border since 1731
• CT-15, the Merritt Parkway, an expressway limited to cars, built in 1938
• I-95, the longest north-south Interstate, 1,900 miles from Maine to Florida.
• US-1, a federal highway running from Maine to Florida, replaced the Old Post Road in 1807
• the Old Post Road, now Old Kings Highway in Darien and Flax Hill Road in Norwalk
• the New York, New Haven, and Hartford Railroad, built in 1848

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 (The National Map of USGS).

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.

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.

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. Along the left side of the map is West Norwalk Road. Crossing the river two-thirds of the way up is Fillow Street, which continues across the top half of the map. Between Old Rock Lane and Fillow Street are a saw mill, an axe helve factory, a sash & blind factory, a saw mill, and a feed mills. To the left of the sash & blind factory is Stephen Mather Road proceeding west from West Norwalk Road into Darien. 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. Fox Run Road goes north from Fillow Street to the top of the map, where it meets Ponus Avenue. 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. On the right side of the map is Taylor Avenue, which starts at Fillow Street and runs south. 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.

Old Red Mill in Darien

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).

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

1894 picture of the Old Red Mill, Darien, Conn. From the Norwalk side of the Five Mile River, the old gravel Post Road (now Old Kings Highway North) 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. See: Red Mill on the Old Post Road

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.
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.

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 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 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 bridge 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.

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.