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Road cycling routes

Chepstow Castle – Old Wye Bridge loop from Chepstow

Road cycling routes

Chepstow Castle – Old Wye Bridge loop from Chepstow

Moderate

16

riders

Chepstow Castle – Old Wye Bridge loop from Chepstow

01:59

42.7km

490m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: October 14, 2026

Tips

Includes a segment in which cycling is not permitted

After 1.39 km for 134 m

Waypoints

A

Start point

Train Station

1

879 m

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

2

1.21 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.

Tip by

3

1.53 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!

Tip by

4

2.73 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

5

4.03 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

6

13.5 km

View of the Wye Valley from St. Briavels Castle

Highlight • Viewpoint

From the castle down into the Wye Valley amazing views!!

Tip by

7

22.9 km

Dean Forest Cycles & Café

Highlight • Rest Area

Nice shop and cafe with some parking. They carry a good range of gear in the shop and you can end up coming out with more than expected.

Staff are …

Tip by

28.3 km

The Cut

Lake

B

42.7 km

End point

Train Station

Way Types & Surfaces

Way Types

28.2 km

11.9 km

1.61 km

659 m

302 m

< 100 m

Surfaces

41.2 km

1.45 km

< 100 m

< 100 m

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Elevation

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

Highest point (240 m)

Lowest point (10 m)

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Weather

Powered by Foreca

Saturday 17 October

13°C

3°C

0 %

Additional weather tips

Max wind speed: 23.0 km/h

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