Walking the Wye Valley Short Break

Wye Valley Short Break: Return Route from Monmouthby Karen Simons

This summer, I decided to check our route notes for the Circular Wye Valley Short Break between Monmouth and Chepstow.

The outward leg of this circular trail follows the Offa’s Dyke Path north from Chepstow, but it was the return route running south from Monmouth that I chose to walk, marked in red on the map to the right.

This section of the walk follows the river downstream between the two historic towns, climbing high into ancient woodland once famous as a royal hunting ground.

Outward from Monmouth

I started in Monmouth, a town dominated by the two rivers that converge here: the Monnow and Wye. The famous Monnow Bridge and gated bridge house stand on one side and the impressive Monmouth School straddles the Wye on the other.

It is along the Monmouth School playing fields that the walk follows the Wye out of the town and towards Redbrook, where it crosses the Wye to follow the riverbank through gentle farmland, past excellent fishing grounds. A steep climb ascends through woodland onto clear wooded paths, with views of the deep valley below.

The River Wye Near Redbrook

Descending down through the woodland, the Wye is met again at Brockweir. The trail joins a dismantled railway line and country park at Old Station Tintern, before emerging onto a sweep of the river that gives a tantalising glimpse of Tintern ahead. Tintern and its magnificent abbey is well worth a stop to enjoy charming teashops and the setting of this ruined masterpiece.

The Wye near Tintern Tintern Abbey

Leaving the abbey and river below, I climbed again into the woodland above the river valley, this time with a clear view of the Wye as it twisted and turned on the last stages of its journey towards the Severn Estuary.

This part of the walk was particularly enjoyable as it traversed the high wooded valley-side along what was obviously a well-trod panorama walk in Victorian times.

The final leg into Chepstow

Wye Valley ViewpointEmerging through a hewn section of rock, the trail reaches a viewing platform that gives a fine viewpoint not just of the Wye below, but of the spectacular cliffside battlements of Chepstow Castle.

Chepstow Castle is one of my favourite castles in the country. It is a fine example and very well preserved. This view of it is, in my opinion, the only way to see how it was constructed, high above the river basin.

Chepstow Castle at the end of the Wye Valley Walk

Another mile or so of walking brought me out into Chepstow town. The walk finishes here beneath the battlements of Chepstow Castle, but I would recommend you head into the bustling centre, where many a fine inn serves a welcome drink.

Contours Holidays pride ourselves on our expert knowledge of the UK’s trails. We regularly set out to check our routes and directions and to make improvements on the holidays we offer. You can find several write-ups of staff expeditions in our Trail Diaries.

Originally published 25/11/19

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Walk the Wye Valley Short Break

  • Visit the fascinating castles at Monmouth and Chepstow.

  • Admire the view from Wintour’s Leap and spot Peregrine Falcons on the cliff tops.

  • Enjoy beautiful riverside walking in ancient woodlands.

© Contours Walking Holidays Wye Valley Short Break - Circular map
Circular trail beginning at Chepstow
36 miles (57 km)
2nd January to 24th December

Walk the Wye Valley Short Break

Code Tour Duration Difficulty Price per person
WVSB1 A circular trail beginning at Chepstow 3 nights, 2 days walking Demanding £355
WVSB2 A circular trail beginning at Chepstow 4 nights, 3 days walking Moderate £475
WVSB3 A circular trail beginning at Chepstow 6 nights, 5 days walking Easy / Moderate £700