After the town of Chepstow developed and a bridge was built over the Wye, the main road between Gloucestershire and Monmouthshire followed the steep hill directly up the river bank between the bridge and Tutshill – now a footpath linking Chepstow to the Offa's Dyke Path – until a new road looping around Castleford Hill was opened in 1808. This road carried traffic between the two counties until a new bridge was built at Chepstow in 1988, whereupon Tutshill was bypassed.