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Chepstow Castle – Chepstow Castle loop from Chepstow

Routes

Hiking trails & Routes

Chepstow Castle – Chepstow Castle loop from Chepstow

Easy

hikers

Chepstow Castle – Chepstow Castle loop from Chepstow

01:29

5.32km

100m

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: April 19, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Wye Valley National Landscape

Waypoints

Start point

Train Station

Get Directions

123 m

First Class Café

Highlight • Cafe

Good place to finish the route at Chepstow train station. Traditional cafe where they still make tea in a pot. No frills, no nonsense, good service.

Tip by

569 m

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.

Tip by

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

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

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

1.47 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 …

Tip by

4.76 km

Naked Boatman Statue

Highlight • Monument

4.85 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.

Tip by

5.32 km

End point

Train Station

Way Types & Surfaces

Way Types

2.28 km

1.10 km

699 m

684 m

454 m

< 100 m

Surfaces

3.04 km

1.84 km

268 m

< 100 m

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)

Weather

Friday 26 June

27°C

16°C

-- %

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Comments

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Chepstow Castle – Chepstow Castle loop from Chepstow

First Class Café

Viva Vita Italian Restaurant

Gloucester Hole

Bird Compass Mosaic, River Wye

Chepstow Castle

Chepstow Castle

Naked Boatman Statue

Coffee#1, Chepstow

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