Chepstow Town Trail

Discover the history, charm, and hidden corners of Chepstow, a town rich in heritage and culture. Nestled at the gateway to Wales and the Wye Valley, Chepstow’s cobbled streets, medieval landmarks, and riverside views make it a fascinating place to explore on foot. The Chepstow Town Trail offers a chance to step back in time, uncovering stories of Norman knights, ancient trade routes, and local legends.

A Walk Through History

The trail takes you through three distinct routes, each showcasing different aspects of the town’s past and present. The Town Centre Trail winds through historic streets, past sites like the Town Gate, St. Mary’s Church, and the Beaufort Hotel, once a coaching inn. Along the way, plaques and markers reveal stories of Chepstow’s past, from its medieval origins to its role in the timber and wine trades.

For those drawn to the river, the Riverside Trail follows the banks of the Wye, leading to the Old Wye Bridge, which straddles the border between England and Wales. This route also takes in the historic port area, where ships once carried local produce and imported goods. The nearby bandstand and riverside gardens provide the perfect spot to pause and enjoy the scenery.

For a scenic climb, the Castle/Dell Trail takes walkers up through Castle Dell, a green space offering panoramic views. This route passes the remains of the Portwall, a medieval defensive structure, and leads into Chepstow Castle, the oldest surviving post-Roman stone castle in Britain.

Plan Your Visit

With a mix of heritage, nature, and stunning viewpoints, the Chepstow Town Trail is an ideal way to explore the town’s unique character. Follow the plaques, enjoy the independent shops and cafés along the way, and immerse yourself in the fascinating history of Chepstow. Whether you choose one trail or combine all three, this self-guided walk is the perfect way to experience the town.

Download the Chepstow Town Trail and Map as a PDF here.