About PetersPioneersFive Mile River

By Peter Biggins

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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.

1789 Colles Atlas of Red Mill
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.
1867 Map of Darien
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
230 Old Kings Highway North, Darien, Connecticut. March 2006.
Canaan Parish
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).

West Side of the River - Right Bank
River

East Side of the River - Left Bank
Scenic Drive,
Lewisboro, New York
Headwaters - 565 feet NY-123 - Smith Ridge Road,
Lewisboro, New York
Puddin Hill Road, New York/Connecticut border since 1731 - mile 0.1
Lukes Wood Road,
New Canaan
River CT-123 - Smith Ridge Road, New Canaan
Michigan Road, New Canaan - mile 1.2
Lukes Wood Road,
CT-124 Oenoke Ridge Road,
New Canaan
River
New Canaan Reservoir - 449 feet
CT-123 - Smith Ridge Road
Summersweet Lane,
Indian Rock Road, New Canaan
Country Club Road, New Canaan - mile 3.0
CT-124 Oenoke Ridge Road,
New Canaan
River Lambert Road, New Canaan
Lambert Road, New Canaan - mile 3.2
Lambert Road,
CT-124 Oenoke Ridge Road,
Parade Hill Road,
Riverbank Court, New Canaan
Old Saw Mill
River Brookwood Lane,
CT-123 - Smith Ridge Road,
Glen Drive, New Canaan
CT-123 - Smith Ridge Road, New Canaan - mile 4.3
CT-123 - New Norwalk Road, New Canaan River River Road,
New Canaan
Old Grist Mill
CT-123 - New Norwalk Road and Locust Avenue and Brushy Ridge Road, New Canaan - mile 4.6
Summer Street,
Main Street,
New Canaan
River CT-123 - New Norwalk Road,
Old Kings Highway,
New Canaan
Brook Street, New Canaan - mile 4.7
Summer Street,
Main Street,
New Canaan
Old Saw Mill
River CT-123 - New Norwalk Road,
Old Kings Highway,
New Canaan
CT-106 - East Avenue, New Canaan - mile 5.0
Millport Avenue,
Main Street,
New Canaan
Old Saw Mill, Grist Mill
River,
Mill Pond - 200 feet
Wastewater Treatment Plant,
CT-123 - New Norwalk Road,
Old Kings Highway,
New Canaan
Lakeview Avenue, New Canaan - mile 5.2
Millport Avenue,
Main Street,
New Canaan
River Lakeview Cemetery
CT-123 - New Norwalk Road,
Old Kings Highway,
New Canaan
Old Norwalk Road, New Canaan - mile 5.7
White Oak Shade Road,
New Canaan
River Marvin Ridge Road,
New Canaan
Hidden Brook
Nursery Road, New Canaan - mile 6.4
White Oak Shade Road,
New Canaan
River Marvin Ridge Road,
New Canaan
CT-15 - Merritt Parkway, New Canaan - mile 6.5
Built in 1938
White Oak Shade Road,
White Oak Shade Lane, New Canaan
West Norwalk Road, Norwalk
River Marvin Ridge Road,
New Canaan
Weed Avenue, Grey Squirrel Drive,
Meeting Grove Lane, Norwalk
Old Rock Lane, Norwalk - mile 6.8
Old Saw Mill & Axe Helve Factory
Old Sash & Blind Factory
West Norwalk Road,
West Lake Court, Norwalk
River,
Millard Pond,
Florsheim Pond
Princes Pine Road,
Pin Oak Lane,
Alewives Road,
Fillow Street, Norwalk
Old Feed Mill, Saw Mill
Fillow Street, Norwalk - mile 7.8
West Norwalk Road
Libby Road,
Watering Lane,
Morehouse Lane, Norwalk
River Geneva Road, Bonnybrook Road and Trail,
Holy Ghost Fathers (Hanford) Brook
St. Johns Cemetery
Norwalk Community College
Richards Avenue, Norwalk
West Cedar Street, Norwalk - mile 8.8
Present Stone Arch Bridge built in 1910
West Norwalk Road, Riverwalk Lane,
Norwalk
River Richards Avenue, Beechwood Road,
Norwalk
US-1 - Post Road, Darien - Connecticut Avenue, Norwalk - mile 9.4
Replaced Old Post Road in 1807
US-1 runs 2,369 miles from Key West to the Canadian border
Darien/Norwalk border, the Perambulation Line, proceeded 37.5 degrees northwest from bridge after 1807
I-95 northbound Exit 13 ramp, Darien, goes under the I-95 bridge alongside the River River
Darien/Norwalk border after 1807
Double Tree Hotel
Richards Avenue, Norwalk
I-95 - mile 9.5
Darien bypass built in 1952
Runs 1,908 miles from Miami to the Canadian border
Red Mill Lane, Darien

Old Grist Mill, Saw Mill
River
Darien/Norwalk border after 1807
Old Mill Pond - 40 feet
Richards Avenue,
Shadybrook Lane,
Norwalk
Old Kings Highway North, Darien - Flax Hill Road, Norwalk (Old Post Road - Country Road in Colonial days) - mile 9.8
The 1789 Colles atlas shows the river is 48 miles from Federal Hall
George Washington travelled here in 1756, 1775-76, and 1789, as Colonel, General, and President
Darien/Norwalk border, the Perambulation Line, proceeded 37.5 degrees northwest from bridge from 1686 to 1807
Bridge rebuilt in 1994
Raymond Street,
Red Rose Circle,
Chasmers Pond Road, Darien
River
Darien/Norwalk border
Chasmers Pond
Cottontail Road, Rowayton Avenue,
Five Mile River Cemetery,
Keelers Brook,
Pheasant Lane, Rowayton Court, Norwalk
New Haven Railroad - mile 10.7
Built in 1848
Raymond Street,
Musket Lane, Red Rose Circle,
Chasmers Pond Road, Darien
Old Grist Mill
River
Darien/Norwalk border
Rowayton Avenue, Carolyn Court
McKendry Court, Jacob Street, Norwalk
Old Feed Mill and Sash, Door & Blind Factory
CT-136 - Tokeneke Road, Darien - Cudlipp Street, Norwalk - mile 11.2
Five Mile River Road,
Butlers Island,
Darien
Mouth of the River
Long Island Sound Inlet
Darien/Norwalk border
Five Mile River Harbor
Sea Level - Tidal
Cudlipp Street
Rowayton Avenue,
Pinkney Park
Rowayton village
Long Island Sound - mile 12.2
← Rippowam (Mill) River is five miles west - Saugatuck River is five miles east →
Greens Ledge Light, built in 1902, one mile from shore (Tide Times)
6.6 miles across the Sound to Eatons Neck Point on the North Shore of Long Island
Notes:
1. The land north of the New York/Connecticut border was part of Cpnnecticut prior to 1731.
2. New Canaan was part of Stamford and Norwalk prior to 1801
3. Darien was part of Stamford prior to 1820.

Saw and grist mills
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.
saw mills and a grist mill
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 and factories
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.
Saw and grist mills
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).
Feed mill and sash, door & blind factory
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.
Grist mill
1867 Darien Map. Grist mill on the Five Mile River in the Five Mile School Ditrict of Darien, on the present-day Tokeneke Road.
Feed mill and sash, door & blind factory
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.
Grist mill
1867 Norwalk Map. Rowayton is called South Five Mile River. The Five Mile River is on the left. Wilson Cove is on the right.
Five Mile River
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.
Five Mile River
Map of of the Five Mile River. Source: Five Mile River Watershed Based Plan, The South Western Regional Planning Agency, 2012.

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