Old Wye Bridge – Chepstow Castle loop from Chepstow

Routes

Hiking trails & Routes

Old Wye Bridge – Chepstow Castle loop from Chepstow

Easy

3.7

(3)

hikers

Old Wye Bridge – Chepstow Castle loop from Chepstow

01:52

6.91km

90m

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: October 14, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Wye Valley National Landscape

Waypoints

Start point

Bus stop

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2.81 km

Old Wye Bridge

Highlight • Castle

On a lighter note, 3 weeks ago I did a 53 mile round trip to Chepstow only to find, on getting there, that I'd left both my phone and camera (and money!) at home. Doh!

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3.08 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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3.11 km

Bandstand and Riverside Pub on the Green

Highlight • Structure

Lovely spot for a rest by the river. Pub has outdoor seating and there’s a bandstand on the green nearby.

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3.11 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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3.61 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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3.63 km

Parish and Priory Church of St Mary (Chepstow)

Highlight • Religious Site

4.06 km

Chepstow Castle

Highlight • Viewpoint

Standing proudly on a limestone cliff above the River Wye, Chepstow Castle is a magnificent fortress with a history that stretches back nearly 1,000 years. Founded in 1067 by Earl …

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