Wentwood and Gray Hill

The ancient forest of Wentwood and an atmospheric hill steeped in antiquity




5.5 miles (8.8kms)

900ft (270m)
2hrs 30min

About the walk

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.

Walk directions

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.

Additional information

Woodland tracks and bridleways, some sketchy field paths (7 stiles)

Woodland, pastoral valley, bracken-covered hill

Can run free in woods and on Gray Hill

OS Explorer OL14 Wye Valley & Forest of Dean

Foresters’ Oaks Picnic Site, just north of Wentwood Reservoir

None on route

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About the area

Discover Newport

The area of Newport neighbours Monmouthshire and is home to a cathedral city of the very same name again. Situated 12 miles from Cardiff, on the mouth of the River Usk, the Normans built a castle here. But Newport really grew up in the 19th century when its port became the place from which to export coal around the world – until Cardiff took over in the 1850s. It was also the site of the last large-scale armed insurrection in Britain, the Newport Rising of 1839.

The docks may have declined in importance, but Newport survived, building on manufacturing, engineering and service industries – some government departments are located here too, such as the passport office. The city is also reinventing itself. First off, it was granted city status in 2002, beating off competition from five other Welsh rivals, including Aberystwyth and Wrexham. It also opened the Usk footbridge in 2006, which won a number of awards, and attracted some big-name discount retail outlets. A few years later, it hosted the prestigious 2010 Ryder Cup at the nearby Celtic Manor Resort.

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