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Bike touring routes & trails

Chepstow Castle – Chepstow Castle loop from Chepstow

Bike touring routes & trails

Chepstow Castle – Chepstow Castle loop from Chepstow

Moderate

3

riders

Chepstow Castle – Chepstow Castle loop from Chepstow

02:07

32.0km

390m

Cycling

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

Last updated: July 31, 2026

Tips

Cycling is not permitted along parts of this route

After 990 m for 100 m

After 18.4 km for 54 m

After 21.9 km for 214 m

Waypoints

A

Start point

Train Station

Get Directions

1

1.04 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

2

1.24 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

15.0 km

Caer-went Roman Town

Archaeological Site

4

15.3 km

Caerwent Roman Town Walls

Highlight • Historical Site

Amazing Roman walls remain, but not much else in Caerwent

Tip by

5

17.9 km

Caldicot Castle

Highlight • Historical Site

lovely place for a picnic.

Tip by

6

22.1 km

View of the Severn Bridge from Black Rock

Highlight • Bridge

7

30.7 km

Chepstow Woodland Path

Highlight • Viewpoint

Pretty traffic-free route in and out of Chepstow towards the Severn Bridge. Look over the fence on the right for a nice view out over the town.

Tip by

B

32.0 km

End point

Train Station

Way Types & Surfaces

Way Types

21.3 km

4.85 km

2.49 km

2.21 km

489 m

347 m

250 m

Surfaces

21.3 km

9.71 km

543 m

250 m

< 100 m

< 100 m

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Elevation

Elevation

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

Highest point (150 m)

Lowest point (0 m)

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Weather

Powered by Foreca

Thursday 30 July

23°C

9°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

to get more detailed weather forecasts along your route

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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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