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Road cycling routes

Monnow Bridge and Gatehouse – Chepstow Castle loop from Caldicot

Road cycling routes

Monnow Bridge and Gatehouse – Chepstow Castle loop from Caldicot

Hard

44

riders

Monnow Bridge and Gatehouse – Chepstow Castle loop from Caldicot

03:38

73.5km

1,030m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. 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

A

Start point

Train Station

Get Directions

5.80 km

Parson's Wood

Forest

2

12.8 km

B4293 Climb from Chepstow to Devauden

Highlight • Viewpoint

Rode this in Aug 21 up to Devauden (not down to Chepstow), a steady climb with gorgeous views of nearby valleys and the distant Brecons. Nothing desperately steep and the tarmac is not too bad either!

Tip by

3

14.8 km

Tree-Lined Road Towards Devauden

Highlight (Segment) • Viewpoint

Resurfaced road a smooth rolling strip of tarmac through the forest. It's beautiful in autumn with all the colours or amazing in spring as the forest starts to grow again!

Tip by

17.9 km

Crumbland Plantation

Forest

5

21.5 km

View of the Brecon Beacons from Wye Valley Country Roads

Highlight • Viewpoint

6

26.8 km

View of the Brecon Beacons from Mitchel Troy Common

Highlight • Viewpoint

Spectacular views west from Mitchel Troy Commonon a clear day towards Abergavenny, Blorenge, Sugar Loaf & the Breckon Beacons.

Tip by

7

31.0 km

Monnow Bridge and Gatehouse

Highlight • Bridge

Sometimes referred to as Monmouth Bridge, Monnow Bridge is a charming medieval stone gated crossing, the last fortified river bridge in Britain. Once, this kind of crossing was a common …

Tip by

8

58.5 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

9

59.8 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

10

62.6 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

B

73.5 km

End point

Train Station

Way Types & Surfaces

Way Types

63.1 km

8.57 km

749 m

621 m

406 m

156 m

Surfaces

66.2 km

7.09 km

164 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.

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Weather

Powered by Foreca

Tuesday 26 May

31°C

17°C

47 %

Additional weather tips

Max wind speed: 21.0 km/h

to get more detailed weather forecasts along your route

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

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