Chepstow Castle to Wyndcliff Wood — Wye Valley Way

Embark on a moderate hike along the Chepstow Castle to Wyndcliff Wood section of the Wye Valley Way, covering 9.8 miles (15.8 km) with an elevation gain of 1215 feet (370 metres). This route typically takes about 4 hours and 30 minutes to complete. You will traverse dense woodlands, featuring ancient beech and yew trees, and encounter narrow, sometimes steep paths. The trail offers spectacular gorge scenery and numerous viewpoints overlooking the River Wye, including panoramic vistas of the Wye Valley and the Severn Bridges. A highlight is the historic Chepstow Castle, standing proudly on a limestone cliff above the river, marking either your start or finish. Be prepared for some strenuous sections, especially around Wyndcliff Wood, which require good fitness and sure-footedness. You will find the famous 365 Steps here, which are very steep and uneven.

This trail is generally considered moderate, but some parts can be challenging. You should plan for the 4 hours and 30 minutes duration, allowing extra time to enjoy the views. The route involves both woodlands and some road sections. Consider starting early to make the most of daylight, especially if you plan to explore the viewpoints.

This section of the Wye Valley Way is part of an internationally important protected landscape, the Wye Valley Area of Outstanding Natural Beauty. The trail immerses you in a landscape that has captivated visitors for centuries, including famous painters and poets. You will pass through Piercefield Park, a Grade I listed historic landscape from the 18th century, which features historic viewpoints like The Lover's Leap. The Eagle's Nest Viewpoint, built in 1828, offers one of the best views in the Wye Valley from its position at 770 feet (235 meters).