Oldest Roads in America

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America is not only home to a number of historic towns, it is also home to a number of historic roads connecting these towns. The roads on this list were all built in the 17th century and parts of them still exist today.

The following is a list of the oldest roads in America:

King’s Highway (1650):

King’s Highway is a 1,300-mile-long road laid out from 1650 to 1735 from Boston, Mass to Charleston, South Carolina. This makes it the oldest road in America.

King Charles II ordered the road’s construction to help link the various English colonies on the East coast in order to improve trade and travel and unify the 13 colonies.

Construction on the road began in 1650 and continued into the 1730s. The construction of the road involved upgrading existing Native American trails and local roads as well as building new sections of road.

The remains of King’s Highway, Parallel to U.S. Route 1, Woodbridge, Prince William County, VA, photo by Historic American Buildings Survey

The road connected numerous colonies, passing through major settlements like Boston, New York City, Philadelphia and Baltimore, before reaching Charleston.

In the 20th century, parts of the King’s Highway were later incorporated into the U.S. Highway system, such as U.S. Route 1 and parts of U.S. Route 9.

Some sections of the old road still exist and are marked by historical landmarks and mile markers and are listed on the National Register of Historic Places.

Albany Post Road (1669):

Albany Post Road was a 150-mile-long mail delivery route that connected New York City and Albany, NY.

Albany Post Road was originally part of the Wickquasgeck Trail, which was a Native American trail that became a vital route for early Dutch settlers when they arrived in the New York area in 1624.

After the British took control of the area in 1664, they built Albany Post Road in 1669 to improve official communications and postal services between New York City and Albany.

Milestone, Old Albany Post Road, Hyde Park, Dutchess County, NY

The road was formalized as a postal route in 1703 and milestone were placed along the road to mark the distances in the 18th century.

In the 20th century, parts of Albany Post Road were incorporated into the modern highway system, such as U.S Route 9. Parts of the old road have been preserved as historic routes, such as the Old Albany Post Road in Philipstown, New York which is listed on the National Register of Historical Places.

Mohegan Road (1670):

Mohegan Road was a road built in 1670 between Norwich and New London in the colony of Connecticut.

In 1792, Mohegan Road became a turnpike, making it the first turnpike in the state and only the second turnpike in America at the time.

In 1922, Connecticut Route 32 was built and incorporated Mohegan Road into the new route. Route 32 was constructed as a north-south route through the eastern part of Connecticut, linking various towns and cities, including New London, Norwich, and Willimantic.

Boston Post Road (1673):

Boston Post Road was a mail delivery route built in 1673 between Boston, Mass and New York City. The road was used by post riders to deliver mail.

The road became a part of the King’s Highway, the oldest road in America. In 1753, stone markers were placed at mile points along the route.

Milestone, State Route 9 (Boston Post Road), Spencer, Worcester County, MA, photo by Historic American Buildings Survey

By the early 18th century, the Boston Post Road consisted of three main routes:

Upper Post Road: This was the northernmost route and it traveled through Springfield, Worcester, and other towns in central Massachusetts before reaching Boston. This route closely followed the old Native American trails.

Lower Post Road: This was the southernmost route, also known as the “Old Post Road,” and it went through southern Connecticut and Rhode Island, passing through towns like New Haven and Providence.

Middle Post Road: This route was built later and it took a more direct path from New York City through Hartford, Connecticut, and then to Boston.

In 1925, two routes of the Boston Post Road, Upper Post Road and Lower Post Road, became U.S. Route 20 and U.S. Route 1.

Farm Highway (1696):

Farm Highway was built in Connecticut in 1696 and was designated a highway on December 7 of that year.

The road was built to connect the farms and settlements between Norwalk and New Haven and was laid out on the south side of Mischa Hill in Trumball, CT. It is considered the third oldest documented highway in Connecticut after Mohegan Road and Boston Post Road.

In the 1932, Connecticut Route 108 was constructed and Farm Highway was incorporated into Route 108.

A History of the Old Town of Stratford and the City of Bridgeport, Connecticut, Reverend Samuel Orcutt, Fairfield County Historical Society, 1886, Vol. II, page 1039
Motavalli, Jim. “The Boston Post Road: A Path Through History.” New York Times, 7 Sept. 2010, archive.nytimes.com/wheels.blogs.nytimes.com/2010/09/07/the-boston-post-road-a-path-through-history/
“Boston Post Road Fact Sheet.” U.S. Department of Transportation, Federal Highway Administration.
“Historic Transportation.” Town of Durham CT, townofdurhamct.org/subpages/historic-transportation
Curland, Richard. “Historically Speaking: Stretch of Route 32 was second-oldest turnpike in nation.” Norwich Bulletin, 15 Aug. 2019, norwichbulletin.com/story/news/columns/2019/08/25/historically-speaking-stretch-route-32/4385515007/
“Connecticut Highway Timeline.” Kurumi, kurumi.com/roads/ct/ct-chrono.html
“King’s Highway.” Prince William Virginia, pwcva.gov/department/historic-preservation/kings-highway-historic-site

“The Albany Post Road.” New York Times, 27 Feb. 1914, nytimes.com/1914/02/27/archives/the-albany-post-road.html
“Mile Markers Along the Old King's Highway.” New England History Walks, newenglandhistorywalks.blogspot.com/2013/05/mile-markers-along-old-kings-highway.html

About Rebecca Beatrice Brooks

Rebecca Beatrice Brooks is the author and publisher of Historic Sites USA. Rebecca is a freelance journalist and history lover who got her start in journalism working for small-town newspapers in New England after she graduated from the University of New Hampshire with a B.A. in journalism.

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