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.

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.

Five Mile River

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.

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 boarder between Darien and Norwalk south of the Post Road.

The mouth of the river is at Long Island Sound, about 12 miles from the headwaters in New York State.

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 twe 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).

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.

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.

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. 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.

1867 Darien Map. Grist mill on the Five Mile River in the Five Mile School Ditrict of Darien, on the present-day Tokeneke Road.

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.

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.

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