Boston Post Road - History

History

The Upper Post Road was originally called the Pequot Path and had been in use by native Americans long before Europeans arrived. Some of these important native trails had seen so much traffic over the years that they were two feet below the surrounding woodland.

What is now called the Old Connecticut Path and the Bay Path were used by John Winthrop the Younger to travel from Boston to Springfield in November, 1645, and these form much of the basis for the Upper Post Road.

The colonists first used this trail to deliver the mail using post riders. The first ride to lay out the Upper Post Road started on January 1, 1673. Later, the newly-blazed trail was widened and smoothed to the point where horse-drawn wagons or stagecoaches could use the road. The country's first successful long-distance stagecoach service was launched by Levi Pease along the upper road in October, 1783.

During the 19th century, turnpike companies took over and improved pieces of the road. Large sections of the various routes are still called the King's Highway and Boston Post Road. Much of the Post Road is now U.S. Route 1, U.S. Route 5, and U.S. Route 20.

Mileposts were measured from the intersection of Broadway and Wall Street in New York (one block west of Federal Hall) and from the old Boston city-line on Washington Street, near the present-day Massachusetts Turnpike.

The Metropolitan Railroad Company was chartered in 1853 to run streetcars down the stretch of the road on Washington Street in Roxbury, which is now served by the MBTA Silver Line. The Upper and Lower Boston Post Roads were designated U.S. Routes 1 and 20 in 1925 (though Route 20 has since been substantially modified).