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Chepstow Castle – Chepstow Castle loop from Chepstow

Routes

Running trails & routes

Chepstow Castle – Chepstow Castle loop from Chepstow

Moderate

5.0

(3)

runners

Chepstow Castle – Chepstow Castle loop from Chepstow

01:28

13.5km

230m

Running

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: May 12, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Wye Valley National Landscape

Waypoints

Start point

Bus stop

Get Directions

1.22 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

1.40 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.

Tip by

7.61 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

8.90 km

Tidenham Chase Climb

Highlight • Climb

Beautiful climb at a consistent 6-7% gradient with glorious views to the right over the Severn Estuary

Tip by

11.9 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

12.2 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

12.4 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

13.5 km

End point

Bus stop

Way Types & Surfaces

Way Types

10.2 km

1.40 km

880 m

780 m

222 m

< 100 m

Surfaces

9.57 km

3.09 km

685 m

119 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

Monday 29 June

22°C

13°C

80 %

Additional weather tips

Max wind speed: 17.0 km/h

to get more detailed weather forecasts along your route

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

Coffee#1, Chepstow

Viva Vita Italian Restaurant

View of the River Wye from Wintour's Leap

Tidenham Chase Climb

Bird Compass Mosaic, River Wye

Chepstow Castle

Chepstow Castle

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