Contours Staff Member Rosalie takes a multi-day walk along the River Wye on our circular Wye Valley Short Break.

An Autumn Adventure Along the Wye

A map of the Circular Wye Valley Short Break offered by Contours Walking Holidays, travelling from Chepstow to Monmouth and back again along either bank of the River Wye.

by Rosalie Smith

In October 2023, an opportunity came up to check Contours Holidays’ route notes for our Circular Wye Valley Short Break.

36 miles through gorgeous countryside from Chepstow to Monmouth and back on either side of the River Wye seemed unmissable for my first solo trip, as well as a great way to get to know one of our popular Welsh holidays, so I volunteered to go out and check the trail.

Setting out on the Wye Valley Short Break

I started my walk waving goodbye to Chepstow and its magnificent castle as I crossed the bridge to begin my adventure.

The remarkably complete ruins of Chepstow Castle rise above the River Wye on a bright day.

It being Wales in October, I had planned for rain, but this proved unnecessary! I was lucky enough to be walking in some of those sunny autumn days which can truly be treasured out in the countryside. The sense of calm achieved walking through fields and woods with nothing but my map, headphones and walking snacks was such a refreshing experience.

This first day took me up Offa’s Dyke Path, following the popular trail through fields and up onto shady wooded paths with stunning views that took my breath away — even when I wasn’t walking uphill!

A well-beaten earth pathway leads along a fenceline between a bower of shady trees.

The Wye Valley Walk clambers up onto Offa's Dyke, offering views down over the leafy Wye Valley with the river at the bottom.

The views from Offa’s Dyke can make you feel on top of the world: even large buildings like Tintern Abbey appear tiny in the distance. The history of this landscape, with Tintern Abbey and the castles at both Chepstow and Monmouth taking you back 500 years, left me wondering just how many people had walked this trail before me.

As I reached Redbrook-on-Wye, I was very grateful that I would not be staying in one of those ancient builds and had a luxurious room waiting for me, complete with a bath to bathe my tired feet.

Day two: rounding the midpoint

On my second day, the landscape changed, which is one of the great features of this trail. After following Offa’s Dyke past the Kymin, a Georgian banqueting house visited by Lord Nelson, I stopped in Monmouth to pick up some lunch for myself.

The view from high up: rounded hills covered with leafy trees surround a small town and a bridge crossing the River Wye.

From here, the map takes you down into the Wye Valley to follow the river. This was a wonderful contrast to the great heights of the dyke. The riverbank offered a flatter walk, with the occasional swan enjoying a swim alongside.

The view across the quiet river provided a perfect backdrop to take some quiet time away from all the rushing about and business of everyday life. I sat and picnicked on the bank, enjoying the calm afforded by such a tranquil spot.

An arched bridge stands in the distance, with the River Wye running calmly in the foreground.

As I ambled into Tintern to find that night’s accommodation, I passed through The Old Station, where I was able to learn a little more about some local legends and historical figures. I even got to see a few in the late afternoon sun!

A series of statues surround a standing stone in the middle of a field, with autumn sunlight streaming down over the scene.

Concluding my hike

The final day’s walking took me past Tintern Abbey, which I had seen from up on the dyke on my first day, before I ascended again to some simply stunning views over the river. The trail then leads you through shady woods, following well-marked paths.

This was the point in my adventure where I saw the most other people out on the trail and it was nice to say a brief hello to other walkers out enjoying the day.

A view upward at the daunting ruin of Tintern Abbey.

Views out over a wide and slow-moving turn of the river.

On reaching Chepstow again, I felt a massive sense of achievement at having completed my first solo trip, staying in three lovely accommodations and really enjoying the moment and the beautiful nature around me over all 36 miles.

As I explored the castle before collecting my luggage and heading home, I was already wondering where I might explore next. This experience has really given me a taste for making time to tune out the world and take in what the British countryside has to offer!

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.

Interested in walking the Wye Valley Walk?

Contours Holidays offer five versions of the Wye Valley walking holiday: the full route, north and south halves, and two short break options, including the circular short break Rosalie embarked on. Find your holiday here: