Chepstow — The Conquerors' Shattered Oath

Your adventure begins at the Main Gate of Chepstow Castle, the oldest surviving stone castle in Wales. Commissioned by William fitz Osbern, a close associate of William the Conqueror, its construction began in 1067, shortly after the Norman Conquest. This fortress stretches along a limestone cliff overlooking the River Wye, marking a crucial strategic point between England and the Welsh border. It is here that you unlock the first fragment of a mystery dating back to the castle's very foundation, as the stone walls began to rise, symbols of Norman power.

Continue your investigation towards the Great Tower, at the heart of Chepstow Castle. This massive edifice, a testament to 900 years of architectural history, has witnessed generations of lords and conflicts. Although conservation work is planned around the Great Hall porch from April 20, 2026, restricting access to the original 13th-century doors, the site remains an immersion into the past. The steep path and steps to the ramparts remind you of the challenges of medieval life, as you search for clues in the nooks and crannies of this imposing structure.

The route then leads you along the Castle Walls, an integral part of Chepstow's medieval fortifications. Further south, these walls connected to the Chepstow Port Wall, built in the late 13th century by Roger Bigod II, Earl of Norfolk, to protect the town. These fortifications directly linked the castle, transforming Chepstow into an impregnable stronghold. As you walk along these walls, you visualize the medieval town protected by the River Wye to the north and these imposing ramparts to the south, essential for trade and defense of the border region.

Leaving the castle, your path crosses the cobblestones of Chepstow Market, a historic market in the town center. This commercial district, near Bridge Street, thrived in the shadow of the fortifications and St Mary's Priory Church, a priory church built from the 12th century and linked to the monastic history of the region. It is in the hustle and bustle of this market that you encounter a virtual character, a 13th-century merchant, who holds a crucial piece of the puzzle, revealing information about the alliances and betrayals of the era, essential to understanding the conquerors' shattered oath.

Your quest concludes at Henry Marten's Tower, back at Chepstow Castle. After exploring the sites of the Chepstow Town Trail, from the River Wye to the Port Walls, you piece together the evidence. Wales, with its Wye Valley National Landscape, was the scene of these foundational events. You have traversed 1.5 km of history, deciphered riddles, and interacted with the remnants of an era when William fitz Osbern and Roger Bigod II shaped this land. You carry with you the satisfaction of having unraveled a centuries-old secret, a total immersion in Chepstow's heritage.