A466 road about long and runs through the counties of Herefordshire and Gloucestershire in England, and Monmouthshire in Wales. It runs south from Kingsthorne, on the A49 south east of Hereford to Monmouth, crossing the A40. After crossing the River Wye at the Wye Bridge, Monmouth and Bigsweir Bridge near Llandogo, it follows a picturesque route south down the Wye valley through Tintern and Chepstow to the M48 motorway at junction 2. The road crosses the border between England and Wales at three places along its length: at Buckholt, Redbrook, and Bigsweir. It runs through an Area of Outstanding Natural Beauty, and
England–Wales border Silures, traditionally the area between the rivers Usk, Wye and the Severn estuary. It was centred at different times on "Venta" (Caerwent), from which it derived its name, and "Isca Augusta" (Caerleon). Gwent generally allied with, and at various times was joined with, the smaller Welsh kingdom of Ergyng, centred in present-day southern Herefordshire west of the Wye (and deriving its name from the Roman town of "Ariconium"); and the larger kingdom of Glywysing in modern Glamorgan. The name Glywysing may indicate that it was founded by a British native of "Glevum" (Gloucester). The Battle of Mons Badonicus, circa 500,