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Chepstow sits right on the border where Southeast Wales meets Gloucestershire, acting as a gateway between the Wye Valley and the Severn estuary. The town is built on steep limestone cliffs overlooking the River Wye, and its geography is still dominated by the massive Norman stone castle that marks the bottom of the town. Life here is defined by this dramatic elevation; the high street climbs steadily away from the river toward the town arch, opening up into a mix of independent shops and Georgian townhouses. Because it’s positioned at the junction of the M48 and the main rail line, it serves as a practical hub for anyone needing to reach Bristol, Cardiff, or Gloucester, yet it retains the quiet, functional feel of a traditional market town. You’ll notice the river’s incredible tidal range - one of the highest in the world - which constantly changes the view from the riverside paths and the old cast-iron bridge. It is a place that feels deeply connected to the surrounding landscape, with the Forest of Dean and the limestone cliffs of Wintour's Leap essentially right on the doorstep.