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Hiking trails & Routes

Gloucester Hole – Chepstow Castle loop from Chepstow

Hiking trails & Routes

Gloucester Hole – Chepstow Castle loop from Chepstow

Moderate

4.8

(9)

79

hikers

Gloucester Hole – Chepstow Castle loop from Chepstow

03:13

11.2km

260m

Hiking

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: October 14, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Wye Valley National Landscape

Waypoints

A

Start point

Train Station

1

1.01 km

Gloucester Hole

Highlight • Natural Monument

Can be seen from the opposite bank (Chepstow side) Gloucester Hole, smuggling, storage of tea, explosives or other smuggled goods?? Marked with a Union Jack and only accessible at high tide!

Tip by

2

1.04 km

Bird Compass Mosaic, River Wye

Highlight • Monument

very nice view on the old bridge,too. there are also public toilets close by

Tip by

3

1.31 km

Chepstow Castle

Highlight • Castle

A Castle with parking space/WCs & coffee shop next to it. We parked here to explore the Wye Valley.

Tip by

4

2.96 km

Rocky Outcrop in Wye Valley National Landscape

Highlight • Viewpoint

cool!!!

Tip by

5

3.93 km

View of the River Wye from Wintour's Leap

Highlight • Climb

Wintour's Leap is a noted rock climbing location and viewpoint. It is located near the village of Woodcroft in Gloucestershire, on the English side of the Wye Valley, north of …

Tip by

4.98 km

Viewpoint

Viewpoint

7

5.39 km

View of the River Wye and Cliffs

Highlight • Viewpoint

beautiful at both low and high tide

Tip by

8

10.6 km

Naked Boatman Statue

Highlight • Monument

B

11.2 km

End point

Train Station

Way Types & Surfaces

Way Types

4.87 km

3.23 km

2.32 km

612 m

182 m

Surfaces

4.72 km

3.27 km

1.65 km

1.24 km

290 m

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Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (100 m)

Lowest point (10 m)

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Weather

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Friday 16 October

14°C

4°C

-- %

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