About PetersPioneersFive Mile River

By Peter Biggins

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Red Mill

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.

Five Mile River

The Five Mile River is one of a number of small coastal rivers that empty into Long Island Sound in southwest Connecticut. The next rivers to the west are Little Brook, Goodwives River/Stony Brook, Noroton River, and Rippowam River. The next rivers to the east are Norwalk River, Saugatuck River, Muddy Brook, and Sasco Brook/Great brook.

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 Stateline - 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
Old Grist Mill
CT-123 - Smith Ridge Road, New Canaan - mile 4.3
CT-123 - New Norwalk Road, New Canaan River River Road,
New Canaan
CT-123 - New Norwalk Road 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
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
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
Stone Arch Bridge built in 1910
West Norwalk Road,
Norwalk Lane,
Norwalk
River Richards Avenue,
Beechwood Road,
Norwalk
Post Road, Darien - Connecticut Avenue, Norwalk - mile 9.4
I-95 Exit Ramp River Double Tree Hotel
Richards Avenue, Norwalk
I-95 - mile 9.5
Red Mill Lane

Old Grist Mill, Saw Mill
River
Old Mill Pond - 40 feet
Richards Avenue,
Shadybrook Lane,
Norwalk
Old Kings Highway North, Darien - Flaxhill Road, Norwalk (Old Post Road) - mile 9.8
Bridge rebuilt in 1994
Raymond Street,
Red Rose Circle,
Chasmers Pond Road, Darien
River
Chasmers Pond
Cottontail Road, Rowayton Avenue,
Pheasant Lane, Rowayton Court, Norwalk
Keelers Brook
New Haven Railroad - mile 10.7
Raymond Street,
Musket Lane, Red Rose Circle,
Chasmers Pond Road, Darien
Old Grist Mill
River 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
River
Long Island Sound Inlet
Five Mile River Harbor
Sea Level - Tidal
Cudlipp Street
Rowayton Avenue,
Pinkney Park
Rowayton village
Mouth of the River - mile 12.2
Greens Ledge Light (Tide Times)
6.6 miles across the Sound to Eatons Neck Point on the North Shore of Long Island

Saw and grist mills
1867 New Canaan Map. Saw and grist mills on the Five Mile River in New Canaan, south of present-day Lambert Road and north of present-day Smith Ridge Road.
saw mills and a grist mill
1867 New Canaan Map. Two saw mills and a grist mill on the Five Mile River in New Canaan, south of present-day Brook Street and north of present-day Lakeview Avenue.
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 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 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 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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