About PetersPioneersThe Red Mill on the Country Road

By Peter Biggins

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48 Miles from Federal Hall

In 1989, Peter and Marilyn Carroll Biggins and family moved into a newly-built house 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, then called the Country Road in Darien, then called Middlesex. (Darien was part of Stamford until 1820.)

A 1789 atlas by Christopher Colles shows the Red Mill on the Country Road in Middlesex. A mile marker on the atlas indicates that the Red Mill is 48 miles from Federal Hall on Wall Street in New York City.

1789 Colles Atlas of Red Mill
Mile 48. From 1789 Colles atlas, Map 4, page 7, showing the Country 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.
230 Old Kings Highway North
"The Red Mill at Five Mile River" by Louise H. McLean appears in Volume 4, Number 8, of the The Darien Historical Society Annual for 1982.
230 Old Kings Highway North
230 Old Kings Highway North, Darien, Connecticut. March 2006.

The Country Road

Old Kings Highway was on the original main road between New York and Boston. It was called the Country Road in Colonial times. The road now crisscrosses three newer and straighter routes: the Boston Post Road (U.S. 1) built in 1806, the New York and New Haven Railroad built in 1848, and I-95 built in 1955. The Railroad did not build a bridge; thus, today's Old Kings Highway North and South.

The Boston Post Road is one of the oldest routes in existence in North America. Originally an Indian trail, the road roughly follows the route of US 1. Although many roads are called the Post Road, this one is the most ancient and documented route from Boston to New York. For more on the old Boston Post Road, see:

1789 Country Road Atlas

In 1789, Christopher Colles created A Survey of the Roads of the United States of America. Maps 1 to 7, pages 4 to 10, show the route from New York City to Stratford, Copnnecticut. Below is Map 4, page 7, showing three four-mile road panels Middlesex (Darien). The second panel includes the Noroton section of Midlesex. The third panel shows the rest of Middlesex and the beginning of Norwalk.

Miles are marked on the atlas with dots and mile number. They were measured with a perambulator. The miles from New York City to Stratford, Connecticut, are measured from Federal Hall on Wall Street in New York City.

The north branching roads are marked by letters. The river crossings are marked by squiggly arrows. The following table is a key to Middlesex locations.

RiversNorth Branching RoadsSouth Branching RoadsPoints of Interest
49-48 Keelers Brook
48 Five Mile River
47 Goodwives River
46-45 Stony Brook
44 Noroton (Roton) River
B Keeler Avenue
A Richards Avenue (to Canaan)
Z Brookside Road
Y Sedgewick Avenue (to Oxridge)
X Leroy Avenue (to Canaan)
W Noroton Avenue
U Gardiner Street (to Canaan)
T Hollow Tree Ridge Road (to Canaan)
48 Rowayton Avenue
48-47 Raymond Street
47-46 Locust Hill Road (to Sillicks Farms)
46 Goodwives River Road (to Long Neck)
48 Red Mill (Grist *)
47 Congregational Church (x)
46 Blacksmith (horseshoe)
46-45 Youngs Tavern (tavern sign)
45-44 Noroton Cove
44 Blacksmith (horseshoe)

                               Greenwich                                                         Stamford                                                         Middlesex (Darien)

Federal Hall

In 1789, the year Colles created his atlas of the Country Road, President George Washington traveled the route. Maybe he used the Colles atlas. The atlas mile markers start at Federal Hall, the seat of the new U.S. government in 1789-90. In 1789, the same year the atlas was published, Washington was inaugurated as President of the United States (April 30) and the first United States Congress met (March 4). In 1790, the U.S. government moved to Philadelphia, and Federal Hall reverted to City Hall. In 1812, Federal Hall was razed and replaced by the current Federal Hall building, which served as the U.S. Custom House for the Port of New York, then a U.S. Sub-Treasury in 1862, then the Federal Reserve Bank in 1920, then Federal Hall Memorial National Historic Site in 1939.

Federal Hall
Federal Hall, Seat of Congress, 1790 hand-colored engraving by Amos Doolittle, depicting Washington's April 30, 1789 inauguration.
George Washington inauguration
Oil painting of George Washington's inauguration as the first President of the United States which took place on April 30, 1789.

17 Miles to Fairfield

There is an old stone marker on the Country Road (now Old Kings Highway South) in Darien that says that it is 17 miles from Fairfield. It is located at the point where Goodwives River Road branches off from the Country Road. The 17 miles agrees with the 1789 Colles atlas. Map 4, page 7, of the Colles atlas says that the point where the Goodwives Road branches off from the Country Road (to Long Neck) is 46 miles from Federal Hall. Map 6, page 9, says that the Fairfield is 63 miles from Federal Hall. The difference is 17 miles, same as the distance shown on the mile marker at Goodwives River Road. Perhaps they used the Colles atlas to make the marker. Perhaps the marker goes back to 1789.

Darien is in Fairfield County. The town of Fairfield was the county seat of Fairfield County from 1666 to 1853.

George Washington marker
Stone marker on Old Kings Highway South in Darien where Goodwives River Road branches off that says that it is 17 miles from Fairfield. Photo: James Biggins.
63 miles from Federal Hall
Mile 63. From 1789 Colles atlas, Map 6, page 9, showing Farfield 63 miles from Federal Hall. See also Penfield's Tavern.
46 miles from Federal Hall
Mile 46. From 1789 Colles atlas, Map 4 page 7, showing Goodwives River Road (to Long Neck) 46 miles from Federal Hall.

George Washington and the Country Road

George Washington is known to have traveled on the Country Road in Darien in 1756, 1775-76, and 1789, as Colonel, General, and President.

  • 1756 - Colonel. On or about February 12, 1756, Colonel George Washington of the Virginia Regiment, age 23, passed northbound through Darien as he traveled to Boston to discuss issues related to his rank with Governor William Shirley of Massachusetts. (Shirley was then Commander-in-Chief of British forces in North America.) Washington was accompanied on this trip by Captains George Mercer and Robert Stewart of the Virginia Regiment, as well as his two hired servants, John Alton, and Thomas Bishop. The party left Alexandria, Virginia, on February 4, 1756, and traveled the approximately 450 miles to Boston. Darien would have been approximately 275 miles, which would take nine days at 30 miles per day. He traveled through Philadelphia, New York, and New London. While in New London, they stayed at the home of a friend, Joseph Chew, where they left their horses. On his return trip, he arrived in New London on March 8, 1756. Joshua Hempstead noted Washington’s arrival in his diary: "Col. Washington is returned from Boston and gone to Long Island, in Power's sloop; he had also two boats to carry six horses and his retinue; all bound to Virginia."
  • 1775 - General. On or about June 27, 1775, General George Washington, age 43, passed northbound through Darien as he traveled over 300 miles from Philadelphia, Pennsylvania, to Cambridge, Massachusetts. On June 14, the Second Continental Congress had created a Continental Army, to be formed out of the individual militias of the Thirteen Colonies. The next day, Congress created the position of Commander-in-Chief of the Continental Army, and unanimously elected Washington to that position. Congress formally presented him with his commission on June 19, and he departed Philadelphia, Pennsylvania, on June 23, headed for Massachusetts. After traveling over 300 miles in ten days, he arrived at Cambridge, Massachusetts on July 2, and took command of the siege. He probably traveled through Darien on the fourth day, June 27.
  • 1776 - General. On April 12, 1776, General George Washington passed southbound through Darien as he traveled 38 miles from Fairfield, Connecticut, to East Chester (Mount Vernon), New York. In Fairfield he stayed at the Sun Tavern, Samuel Penfield, proprietor, on Town Hall Green. In East Chester, he stayed at Charles Guion's Tavern on the Boston Post Road, near East 233rd Street. He was on his way from Boston to New York City. He had just spent ten months as Commander-in-Chief of the Continental Army in the opening phase of the revolutionary War at the Siege of Boston.
  • 1789 - President. On October 16, 1789, the newly inaugurated President George Washington, age 57, likely spent the night at Samuel Penfield’s Sun Tavern in Fairfield on his tour surveying damage from the Revolutionary War. The destruction from the 1779 burning was so widespread that it was still evident ten years later when Washington wrote: “The destructive evidences of British cruelty are yet visible both in Norwalk and Fairfield, as there are chimneys of many burnt houses standing in them yet.” At the time, it took two days to travel from New York to Fairfield by carriage on the Boston Post Road, so travelers needed a place to stay overnight and refresh their horses.

On Old Kings Highway South, two miles south of our house in Darien, there is an ancient stone mile marker that says "Fairfield 17 Miles." Since Armistice Day in 1932, an historical marker next to the mile marker reminds passers-by that George Washington went by in 1756, 1776, and 1789. The marker is at the intersection of Old Kings Highway South and Goodwives River Road. The marker says "George Washington passed this spot on his way to Boston: February 1756, June 1775, October 1789. Erected in his memory by the civic, patriotic and fraternal organizations of Darien, November 11, 1932."

The Red Mill

As mentioned at the outset, in 1989, Peter an d Marilyn Carroll Biggins and family moved into a newly-built house in Darien, Connecticut, at 230 Old Kings Highway North. The house backs up on the right bank of the Five Mile River. On the side of the house is is the left bak of the mill run. 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 house on the east side of the old mill run. Remnants of the mill are still there.
mill foundation
Remains of the dam after the leaves have fallen in November 2016 from the deck in the rear of out house at 230 Old Kings Highway North.
mill unn
Close up of the remains of the dam.

  • The dam across the river is gone. They say it was blown up in the 1920s. But there is still a long stretch of the dam that can be seen on the other side of the river.
  • The mill pond has no water because the river is no longer dammed up, but outline of the mill pond can still be seen.
  • The mill run has no water in it, but the long straight ditch from the mill pond to the river downstream can still be seen. The portion on the other side ofthe road was filled in when a new bridge was built in 1994.
  • What appears to be a short stretch of the mill foundation can be seen not far from the road on the west side of the mill run. It is about 12 feet long and two feet high and is perpendicular to the mill run.
mill foundation
What appears to be a short stretch of the mill foundation can be seen not far from the road on the west side of the mill run. It is about 12 feet long and two feet high and is perpendicular to the mill run.
mill unn
The mill run has no water in it, but the long straight ditch from the mill pond to the river downstream can still be seen.
The location of the mills can be seen on the 1867 map of Darien. In 1982, Louise H. McLean (1906-2004), past president of the Darien Historical Society, wrote an article on "The Red Mill at Five Mile River" that appears in Volume 4, Number 8, of the The Darien Historical Society Annual.

1867 OKHN map
1867 map showing the grist and saw mills on the Five Mile River. The mills are at the point where the Country Road crosses the Five Mile River. The mill pond is north of the mills. The mill run reenters the river south of the road. The road parallel to the Country Road to the north is the newer Post Road. The road running south from the Country Road is Raymond Street. Published in 1867 by Beers Ellis & Soule. From David Rumsey Map Collection

Following is a timeline based on the 1982 Historical Society article by Louise McLean.

1640The New Haven Colony bought from the Siwanoy Indians a tract of wilderness where the Rippowam River met the waters of Long Island Sound. The Siwanoys lived in small villages of bark-covered wigwams, and spent their lives fishing, hunting, and tending their cornfields. The eastern boundary of the purchase was the Goodwives River (then called Pine Brook)
1644The boundary of Stamford was extended from Goodwives River to the Five Mile River with a purchase from the Roaton Indians
1660John Reed (1633-1730), a Puritan, fled England when the monarchy was restored under Charles II
1684John Reed began to purchase large tracts of wild land at "Five Mile Brook" on the Norwalk side of the stream.
1692John Reed and his son John Jr. applied to the town of Norwalk for a permit "to erect a sawmill at the head of the salt" on the Five Mile River
1699John Reed, age 65 and owner of 1/4 of the mill, transferred his share to his son Thomas and daughter Mary Tuttle
1725The mill site and 17 acres of land were sold to John Reed's son Thomas
1730John Reed Sr died and was buried probably in Old Rowayton Cemetery, also called Brookside Cemetery and Old Five Mile River Cemetery, which the Reed family had laid out in 1723/4
1737The area now known as Darien became Middlsesex Parish, still part of Stamford.
1753The estate of Capt. Jonathan Bates lists a sawmill appraised at 11.5 pounds
1756Colonel George Washington of the Virginia Regiment, age 23, passed the mill as he traveled to Boston to discuss issues related to his rank with Governor William Shirley of Massachusetts.
1758The inventory of Eleazar green lists a sawmill appraised at 11.5 pounds
1767Samuel Richards (1746-1785) bought the farm and gristmill from the Reeds
1776General George Washington, passed by the mill in April on his way back from the Siege of Boston
1772A stagecoach began providiong service on the Country Road between New York and Boston every two weeks
1777Tories from Long Island kidnapped Capt. Richards, father of the mill owner, and 14 other men. They were carried to Long Island by boat and thence to prison in New York City. After four months, Capt. Richards, a very sick man, was released, only to die soon after his return to Norwalk
1789Christopher Colles created his atlas of the Country Road, perhaps in time for use by President George Washington. The atlas has markers showing the miles from Federal Hall on Wall Street in New York City. The Noroton (then Roton) River was 44 miles. The Five Mile River was 48 miles
1789President George Washington, age 57, passed by the mill on his tour surveying damage from the Revolutionary War in Norwalk and Fairfield
1785Samuel Richards sold his house, the gristmill, and much of his land for 400 pounds to his neighbor David Reed, who soon sold it to Nathan Bouton for 450 pounds
1804Noyes Richards, son of Samuel, paid $3,150 for Nathan Bouton's 47 acres, house, barn, miller's house, and gristmill. Noyes had recently married Sally Mather, a granddaughter of Rev. Moses Mather
1804Noyes Richards sold 2/3rds of the mill to Nathaniel Hoyt (1748-1822) of Hoyt Street
1806The new straighter Post Road was completed, as an alternative to the Country Road, on which the mill was situated, replacing it as the main road through Middlesex Parish.
1810The land on which the sawmill stood was purchased by Ralph Hoyt, the son of Nathaniel Hoyt
1820Middlesex Parish, part of Stamford, became the separate Town of Darien
1822John Reed Jr. became the owner of the mill after the death of Nathaniel Hoyt
1825Zalmon Sturges bought the mill from John Reed Jr.
1832Peter Leinberger (Linesburg) of New York City bought the mill from Zalmon Sturges
1835Upon the death of Ralph Hoyt, his sister, Martha Hoyt Reed and her husband John Reed sold the sawmill to Henry bates (1779-1840), son of Jonathan 3rd. The Reeds retained title to the land and miller's house
1843A "spring freshet" washed out the dam
1848The New Haven Railroad came through Darien, crossing the Country Road
1855Nathan Roberts paid Peter Leinberger $1,000 for the mill and Leinberger's house at the corner of Raymond Street.
1894Photo shows the mill half-hidden among trees with a picturesque gravel road and wooden bridge in the foreground
1900The mill was sold to the New York, New Haven, and Hartford Railroad
1908Alexander Raymond dismantled the mill and stored the mill wheel and sold it to the Buttery Mill in Silvermine
1925Harry Street, grandson of Alexander Raymond, used some of the beams from the mill in building his house at 10 Five Mile River Road
1955I-95 came htrough Darien, crossing the Country Road, by then called Old Kings Highway South at Corbin Road
1982Louise H. McLean (1906-2004), past president of the Darien Historical Society, wrote an article on "The Red Mill at Five Mile River" that appears in Volume 4, Number 8, of the The Darien Historical Society Annual
1989Peter and Marilyn Carroll Biggins and family moved into a newly-built house on the east side of the old mill run
Old Red Mill
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.
Old Red Mill
Picture of the grist mill in wintertime.
Old Red Mill
Picture from the Norwalk side of the Five Mile River of the saw mill and the river flowing over the dam in wintertime. In the background is a barn.

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