February 12, 2010

1. The Oldest Road in the United States

The Boston Post Road

©1995 by Beverly Whitaker, Genealogy Tutor

Routes of the Boston Post Road
Lower route_(Southern)_270 miles long
Boston, MA_Dedham, MA_Providence, RI_Mystic, CT_New London, CT _New Haven, CT_Fairfield, CT_Greenwich , CT_Rye, NY_Kingsbridge,NY_New York City

One section of Fairfield's Old Post Road. Photo circa 1909. Note trolley tracks.

The Old Post Road began most probably as simply a trail by the local native Indians. It was along that trail that the first settlers who founded Fairfield in 1639 built their small homes. The road extended 270 miles and was forged by the first overland postman to allow mail to reach the Eastern colonies. (The word "post" meant the stations where the riders changed horses, hence a Post Road). In colonial days it was easier to reach the mother country England, than to travel through the rough terrain between Boston and New York. We often complain about mail service today, but a letter scheduled to leave New York, January 22, 1673, didn't reach Boston until about February 5, 1673. The rider left from the end of Broadway, Fort Amsterdam, crossing rivers, frozen lakes and slugging through dense woodlands. He had to be alert to the dangers of wild animals, bandits and Native People who were not happy about intruders on land where they hunted and lived.

The road has been known as the Great Road and the King's Highway. By the 1830s it had become a regular route for stagecoaches that took two days to travel the entire route. Along the way were several taverns where weary travelers would stop overnight or for drink and hot meals. In 1789 George Washington traveled through the colonies and stopped at many of the Inns, notably the Sun Tavern, which is between the Fairfield Town Hall and Independence Hall.

Many changes have been made since those days. It became more and more necessary to straighten the road as transportation become more sophisticated. Stretches of road were added, and the old sections were tucked away running somewhat parallel to the new Boston Post Road AKA Route #1. In most places they were renamed Old Post Road, as it is here in Fairfield.

It is along this section in Fairfield that can be seen some of the finest old homes and churches in the State. The original five squares of home sites were centered around the Town Hall, and before long some of the existing houses there today, were erected. These houses run the gamut from Colonial, Georgian, Federal, Greek Revival, Victorian styles, and a variety of period revival styles.

Very few streets in any New England town remain untouched by commercialism. Therefore Historic Districts were established around the country, and in 1962, Fairfield's Old Post Road was designated as an Historic District. Now, future generations will see some 18th century homes and the area were the town began.


  1. how could a letter leaving Ny 1673 arrive in Boston 1663? something is wrong with this date.

  2. Thank you!! Heads up notation greatly appreciated.

  3. Enjoyed the article...from a reader in Trumbull