The road is thought to have existed at least from Roman times.

[1] In the Middle Ages it was a typical market street, known as the "Great Causey",[2] with gates at either end and a wider area in the middle for the trading of livestock and the erection of market stalls.

Archaeological investigations at properties in the street, led by the Monmouth Archaeological Society, have revealed both Roman and Norman remains, as well as evidence of mediaeval iron working.

[4] The street is described by architectural historian John Newman as a "pleasingly continuous array of C18 and early C19 shops and houses, in the main modestly two-storeyed, with several Victorian interventions".

[5] Notable buildings include Cornwall House, The Vine Tree and the Robin Hood Inn.