About PetersPioneersThe Old Post Road

By Peter Biggins

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48 Miles from Federal Hall

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. The street name is provided in the U.S. Census starting in 1900: Red Mill Road in 1900, Old Post Road in 1910, Old Kings Highway in 1920, and Old Kings Highway North in 1930 and 1940.

A 1789 atlas by Christopher Colles shows the Red Mill on the Old Post 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 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.
230 Old Kings Highway North
230 Old Kings Highway North, Darien, Connecticut. March 2006.

The Old Post Road

Old Kings Highway was on the original main road between New York and Boston. It was called the Post Road or 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 Old 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 Post Road, see:

1789 Colles Map

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, Connecticut. Map 4, page 7, shows three four-mile road panels: Greenwich, Stamford, and Middlesex (Darien's name before 1820). The Middlesex panel shows part of Norwalk and most of Middlesex. The present-day names for the Old Post Road are:

  • southern part of Flax Hill Road in Norwalk
  • Old Kings Highway North (OKHN) in Darien
  • Old Kings Highway South (OKHS) in Darien
  • New Post Road in Darien south of OKHS and north of Hollow Tree Ridge Road.
The Stamford panel includes New Post Road from Hollow Tree Ridge Road in Dariensouth to Stamford.

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 the tip of Manhattan, just south of Federal Hall on Wall Street.

Colles Map 4c - Norwalk and Middlesex (Darien) - Mile Markers 48 to 45 - North: 45° left
1789 Colles Atlas 1789 Colles Atlas 1789 Colles Atlas
1789 Colles Atlas 1789 Colles Atlas

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
From 1789 Colles atlas, Map 1, page 4, showing Federal Hall on Wall Street. St. Paul Chapel up Broadway near the start of Park Row (+), where George Washington prayed following his inauguration. The first Brick Presbyterian Church was on Park Row (x). Mile marker 1 is at Chatham Square at the start of the Bowery.

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.

The 17 is the difference between 63 and 46
on the Colles map as shown to the right.

63 miles from Federal Hall
Mile 63. From 1789 Colles atlas, Map 6, page 9, showing Farfield 63 miles from Federal Hall. Note 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 on the Old Post Road

George Washington is known to have traveled on the Old Post Road in Middlesex (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."

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