Wentwood and Gray Hill

In the early medieval period, Wentwood forest stretched unbroken from the River Usk to the banks of the Wye, dividing the old kingdom of Gwent into Gwent Is Coed (‘Gwent below the wood’) and Gwent Uwch Coed (‘Gwent above the wood’). East of the Wye, it would have reached as far as the much larger Forest of Dean. At that time, the trees were mainly oak and beech, and provided an ideal habitat for large mammals such as deer and wild boar.

The first sustained assault on Wentwood took place under the Normans, who cleared a large area of forest west of Chepstow to found the settlements of ‘Sherriff’s Newton’ (Shirenewton) and Earlswood. However, the Normans also maintained large areas of the forest as hunting preserves belonging to the lordship of Chepstow. In return for their rent, tenant farmers had the right to collect timber from the forest and let their sheep, goats and pigs to forage for food. Any infraction of these rules was dealt with by a special forest court, which convened twice a year in a grove of oak trees known as ‘Foresters’ Oaks’ (close to the entrance of the picnic site). Criminal offences were dealt with separately, and often severely, and the last recorded hanging at Foresters’ Oaks took place in 1829.

Land-hungry farmers and a demand for mature oak trees to build houses and warships led to a further erosion of the woodland area from the 16th century onwards. Ironically, it was the iron industry that saved the heart of the forest, by placing a high value on the timber required for the production of charcoal. However, what remained of the ancient woodland came under intense pressure during World War I, when many native broadleaved trees were felled to provide timber for the trenches. These were largely replaced with conifers, which continue to dominate many areas of the forest. Nevertheless, despite being much reduced in size, Wentwood remains the largest area of ancient woodland in Wales and the ninth largest in the UK.

East of Wentwood, the walk enters a pastoral landscape before climbing steeply west towards the summit of Gray Hill. The hard slog to the top is rewarded by spectacular views across the Severn Estuary and along the Caldicot Levels, as well as inland over the hills of Wentwood. The hill is well known for its Neolithic and Bronze Age remains, which include standing stones, a stone circle and a D-shaped enclosure. Arthur Machen (1863–1947), author of supernatural, horror and fantasy novels, had a mystical fascination with Gray Hill and featured it in a number of his writings.

Turn left out of the car park and follow the road uphill into Wentwood. Opposite a lane on the left, bear right on to the bridle track signed to Earlswood. Follow the steadily ascending bridleway to a major junction of tracks (‘The Five Paths’) and turn right. Immediately fork right by a bench.

Follow the main forestry track downhill, curving right where a smaller track joins from the left. At a T-junction with another track, keep straight ahead on to a bridleway opposite. Fork left, then left again, to reach a gate out of the woods. Descend on an enclosed path to a ford.

Cross a footbridge over the Castrogi Brook on the left, climb to a lane and turn right. Immediately after a house on the right, fork right on to a rough lane. Turn right at a T-junction and descend back towards the Castrogi Brook. Cross the stream and turn immediately left up a footpath signed to Llanfair Discoed.

Climb steeply to a lane and turn left. Keep left at a fork and reach a right-hand bend into the garden of a house. Follow waymark arrows down through the garden and bear right alongside the Castrogi Brook. After a short woodland stretch, the path continues along the left-hand boundary of three fields.

You will eventually arrive at a gate and stile leading on to a lane. Do not join the lane, but take the footpath climbing to the right (‘Gray Hill’). Go through a gap between trees, then bear right to pass a corner of woodland. Maintain direction and climb steeply to a metal gate.

Follow a grassy woodland track up to a field and turn right. Join a stony track by a gate and stile and keep ahead to a waymarker post. Turn left and climb to a stile. Continue uphill along the right-hand field edge. Do not cross a gate ahead, but follow the top edge of the field to the left.

Cross a stone memorial stile on the right into scrubby woodland. At a clear fork, turn left and climb gently along the ridge until a well-trodden path appears on the left. Descend easily to Gray Hill’s prehistoric stone circle, then bear right along a gently climbing path to the summit.

Bear slightly right across the summit area on to a waymarked path that descends steeply through bracken. On reaching a bridleway at the base of the common, turn right and continue on to a track and lane. Emerge at a T-junction with Usk Road opposite the entrance to Forester’s Oaks Picnic Site.