The Historical Milestone was originally placed in 1787 by Major William Taylor in front of his house which stood on the War Memorial grounds. In an attempt to recoup his fortune lost to battle in the Revolutionary War, Major Taylor converted his home into an Inn primarily for people traveling between New York and Hartford. This was a trip that could take three days at that time.

As the milestone indicates, the Taylor Inn was nearly equidistant to both cities and must have been a welcome resting spot for weary travelers.

In 1951, Memorial Drive, the road leading through Roger’s Park was built and the mile stone was removed to the yard of the Scott-Fanton Museum at 42 Main Street.

Members of the Mary Wooster Chapter of The Daughters of the American Revolution found the Milestone several years later and erected it on the front lawn of the War Memorial building, several hundred feet east of its original site.