According to a plaque on the wall outside, The
White Lion, in White Lion Square, Chepstow, was established as a
Coaching House around 1644.
Ivor Waters' book, "Chepstow Parish Registers 1695-1837", has this entry : "September 3rd, 1644. Elizabeth her father unknowen borne in the house of Hughe Masone called the Pye Corner." Ivor Waters' book, "The Town of Chepstow", has this to say :
"Pye Corner; Post Office Square; White Lion Square.
The open space at the top of Bank Street was for over two centuries called Pye Corner. Charles Heath said the name denoted the ‘angle of two streets’. Possibly this was a blocked highway through an earlier Town Gate, perhaps it is a reminder that the White Lion was once known by the sign of the Magpie. The inn dates from the early 17th. century. The first written record of the house is in the parish register for Sep. 3, 1644, when it was ‘the house of Hughe Masone called the Pye Corner’.
At the beginning of the 18th century, all three names occur but for the past two hundred years, the inn has been the White Lion.
The little square continued to be called Pye Corner. In 1799 the Rev. W. Leach’s executors paid £31. 10s. for ‘Pye Corner House and Lands and ye Tolls of Chepstow’. The Pye Corner Lands probably included Portwall Cottage, St. David’s Cottage, and part of what is now the Car Park. When John Hedgings became postmaster in 1840 he moved his office to Pye Corner, ‘in the immediate vicinity of the mail station’, the White Lion. The post office was here until 1880 and Pye Corner became known as Post Office Square, then White Lion Square, and about 1871 was numbered in Bank Street."
Interestingly, according to that same book, Bank Street/Hocker Hill Street was the main road until the late 19C, when High Street superseded the route.