Chepstow Castle – Gloucester Hole loop from Chepstow

Routes

Hiking trails & Routes

Chepstow Castle – Gloucester Hole loop from Chepstow

Easy

hikers

Chepstow Castle – Gloucester Hole loop from Chepstow

01:08

4.07km

80m

Hiking

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: August 18, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Wye Valley National Landscape

Waypoints

Start point

Bus stop

Get Directions

1.13 km

Naked Boatman Statue

Highlight • Monument

1.57 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

1.84 km

Bird Compass Mosaic, River Wye

Highlight • Monument

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

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1.88 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!

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2.33 km

Parish and Priory Church of St Mary (Chepstow)

Highlight • Religious Site

2.35 km

Viva Vita Italian Restaurant

Highlight • Cafe

Stopped here for breakfast and a coffee and the quality was amazing. Has a sheltered outdoor seating area where you can lean your bikes against the wall in sight.

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2.56 km

Coffee#1, Chepstow

Highlight • Cafe

My favourite place to stop for mid-ride coffee & cake or a more substantial lunch. Popular with locals and cyclists, staff are welcoming and friendly and food & drinks are great.

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