Until the 1830s, when Priory Street was built to bypass it, it was the main thoroughfare into the centre of Monmouth from the north-east, linking the market and the parish church.

According to local writer and antiquarian Charles Heath in 1804:[1] Church Street was originally a mere thoroughfare, scarcely wide enough to admit a loaded waggon to pass through it.

On the site of the most respectable part of it was a dirty shore or kennel, and, on the bank above, posts and rails were placed, to secure the passengers from falling into it.

[4] Escaping serious injury, she grabbed the coachman's whip, knocked out some of his teeth with the handle, and marched back to her shop to begin organising a petition for a new road to be built to bypass Church Street.

The prize was won by local architect George Vaughan Maddox, who proposed a new carriage road — now Priory Street — on a viaduct immediately above the bank of the River Monnow.

[5][6] The buildings in the modern street date largely from the early nineteenth century, with continuous three-storeyed, stuccoed terraces on both sides.