Monnow Bridge and Gatehouse – Old Wye Bridge loop from Caldicot

Monnow Bridge and Gatehouse – Old Wye Bridge loop from Caldicot

Hard

riders

Monnow Bridge and Gatehouse – Old Wye Bridge loop from Caldicot

03:36

72.1km

1,020m

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: October 15, 2026

Tips

Includes a segment in which cycling is not permitted

After 61.0 km for 134 m

Waypoints

Start point

Train Station

Get Directions

5.80 km

Parson's Wood

Forest

9.79 km

Coed Mawr

Forest

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!

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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!

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21.5 km

View of the Brecon Beacons from Wye Valley Country Roads

Highlight • Viewpoint

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.

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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 …

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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 …

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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

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61.0 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!

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