Chepstow to Trellech: 13.5 miles
From Chepstow Castle, the Monmouthshire Way leaves the town by following the Wye Valley Walk uphill towards Chepstow Leisure Centre. However, instead of following the Wye Valley Walk into the woodland, the route visits the ruined mansion house of Piercefield House.
The Wye Valley Walk is re-joined for a short stretch before the Monmouthshire Way leaves it again to follow a beautiful route via St. Arvans to Itton and Chepstow Great Wood. Heading north, the Monmouthshire Way visits Ravensnest and passes the 17th century Fountain Inn on its way to the medieval town of Trellech via Catbrook.