CWF 2026 overview

Welcome to CWF26 - Spring Edition!

Having heard from regular festival-goers that there's strong interest in more walking opportunities later in the year, we've taken the decision to split Chepstow Walking Festival 2026 into both a Spring and an Autumn programme. The Autumn programme will run from October 23rd to 25th and more details will be published in August.

Meanwhile, the much-anticipated Spring programme is now complete, with 21 spectacular walks showcasing the very best of the region and led by our amazing team of volunteer walk leaders, local experts and partner organisations. Amazing views, fascinating local history, woodland exploration, geology, wildlife and art all feature this time and there are walks ranging from gentle strolls to more challenging longer-distance hikes.

Headline details can be found below, with more details and online booking via our Ticketsource portal - we've held ticket prices at 2020 levels and there's usually strong demand, so book early to avoid disappointment!

General Information

Adult tickets are £5 each, under 16s are always free, but still need to be booked! Please remember under 18s or vulnerable adults must be accompanied by a responsible person or carer in line with relevant safeguarding guidelines. To enable prices to stay low, email tickets are issued for online bookings, other bookings are acknowledged by email wherever possible (tickets are not required on the day of the walk as leaders will be provided with booking lists in advance). Please see our terms and conditions below.

Walks are graded based on the following features:
Easy - shorter length, some gentle slopes, few stiles, leisurely pace, easy terrain
Moderate - medium length, some stiles, some ascent or descent, modest pace
Energetic - longer length, more stiles, ascent and/or descent, faster pace
Strenuous - challenging distances, steeper/longer ascent and descent, difficult terrain

Some routes are designed to be suitable for dogs - see individual walk listings for details.

PROGRAMME - FRIDAY 10 APRIL

CWF26 walk 1 - Usk Valley Hills, Woodland and Folklore

Friday 10 April / 9:30 start / 7 miles moderate with a few stiles / allow 4 hours / not suitable for dogs

This walk heads from the centre of Usk up onto Usk Lady Hill then to the woodland of Cefn lla, managed by The Woodland Trust. We will look at this diverse environment and delve into some of the folklore and uses of trees on our meander through the woods.

CWF26 walk 2 - Cwmcarfan Hill, Views and Flowers (Trig Point Walk)

Friday 10 April / 10:00 start / 7.5 miles energetic with over 1000ft of ascent / allow 5 hours / not suitable for dogs

This walk from Trellech crosses open farmland up to the Trig Point on Cwmcarfan Hill. The route continues onto Llanishen Far Hill with some of the best extensive uninterrupted views that Monmouthshire has to offer, then to Penarth Brook before dropping down into Woolpitch Wood where hopefully the spring flowers will be starting to emerge. The return route crosses high open fields back to the starting point. A walk not to be missed with brooks, woodland, views and open countryside.

CWF26 walk 3 - The Resistance Walk Revisited

Friday 10 April / 10:00 start / 7.5 miles moderate / allow 4-5 hours / suitable for well-behaved dogs

This walk is always a favourite and tells the story of one of the WWII Special Auxillary Units (Jonah Patrol), a guerilla group operating behind enemy lines and established by Winston Churchill. The route meanders through Wentwood to formerly secret bunkers now preserved as an ancient monument.

CWF26 walk 4 - Oldbury and The Severn Way

Friday 10 April / 10:00 start / 7.5 miles moderate / allow 4-5 hours / not suitable for dogs

A coastal stroll or a quantum leap. This is a lovely wander along the banks of the Severn, visiting an iron age fort, one of the smallest active churches in the UK, an unusual modern "lighthouse", a church with a grand view, and circumnavigation of a nuclear power station. Definitely something a little different!

CWF26 walk 5 - Geology Walk in the Wye Valley

Friday 10 April / 9:50 start / 6.5 miles moderate to energetic / allow 3-4 hours / not suitable for dogs

Join geologist Steve Bennett and Ruth Waycott, from the Wye Valley National Landscape Team, for a ramble through the geology of the lower Wye Valley, finding out what really is beneath our walking boots! The rocks found in this area are mainly sandstones and limestones, which tell of an ancient equatorial world! Today, deep quarries harvest the mineral wealth, whilst towering limestone cliffs are home to peregrine falcons.

CWF26 walk 6 - St Arvans and Oakgrove Stud

Friday 10 April / 10:00 start / 3 miles easy / allow 3 hours / not suitable for dogs

A scenic walk across open pasture with fabulous views across the Monmouthshire countryside. Return via Oakgrove Stud at St Arvans for a rare opportunity to visit some of their very cute residents.

CWF26 walk 7 - Tales of Bridge and River (Caerleon to Newport)

Friday 10 April / 10:00 start / 6 miles moderate / allow 4 hours / not suitable for dogs

A walk from Caerleon to Newport Transporter Bridge following the path of the River Usk. This popular route takes us from countryside to cityscape in the company of Gwent storyteller Christine Watkins and Gavin Jones of the Transporter Bridge Project Team. Along the route we will discover stories and traditions that have gathered around the tidal Usk across the centuries. Arriving at the Transporter Bridge we’ll learn about the current restoration project, before boarding a minibus to return to our starting point in Caerleon.

Please note that due to ongoing construction work it will not be possible to enter the bridge structure this year.

CWF26 event - Following in the Footsteps of Welsh Drovers

Friday 10 April / 18:30 start / evening presentation / not suitable for dogs

Mark Davis worked as a researcher and lecturer in exercise and health science at the University of Bristol. Now retired and living in the Brecon Beacons, he is one of a growing band of Brecon Beacons National Park Ambassadors. The Ambassador programme piqued his interest in droving which has led to his involvement in walks and talks about droving.

This talk will delve into the history and practices of droving. Mark will identify the legacy of droving that is still with us and explore the routes used by Welsh drovers to reach lucrative English markets. Mark will draw on local features related to droving activity in the area.

PROGRAMME - SATURDAY 11 APRIL

CWF26 walk 8 - The Pilgrim Walk

Saturday 11 April / 9:30 start / 11 miles energetic to strenuous / allow 6-7 hours / not suitable for dogs

For the third year we are inviting you to take a circular “Pilgrim” walk to visit some of Monmouthshire’s finest churches. As before walk leader John Brooks will give a short history of each church and a chance to explore. There are some fascinating stories to tell. The walk incorporates the first section of the Lower Wye Valley path with stunning views over the river, churches St Arvans, Mounton, Mathern and St Mary’s in Chepstow, returning to the start via Chepstow Castle.
This has been a very popular format in previous years so please book early to guarantee your place.

CWF26 walk 9 - Caldicot Moor Trig Point, Wales Coast Path and Railway Walk

Saturday 11 April / 10:00 start / 12 miles moderate to energetic (due to distance, mainly flat) / allow 6 hours / not suitable for dogs

This walk begins at Severn Tunnel Junction, walking back to Chepstow following the Welsh Coast Path and accompanied by the Wales Coast Path Volunteer Warden for this stretch of coastline who will provide a wealth of knowledge of the area and the formation of the route. The route starts by finding one of the lowest trig points in Wales, with fabulous views of the Severn Estuary and many points of interest. A different and interesting walk.

CWF26 walk 10 - Lydney Docks, Beer and the Severn Estuary

Saturday 11 April / 10:00 start / 6 miles moderate / allow 3-4 hours / suitable for well-behaved dogs

Starting from the Forest Micro Brewery, the route heads towards the banks of the River Severn, offering views of the historic original bridge and exploring sights of historical interest. At the finish there is an opportunity to relax and sample locally crafted beers and ciders – the perfect way to end a perfect walk.

CWF26 walk 11 - Hidden Chepstow - Look Up

Saturday 11 April / 10:00 start / 1 mile easy / allow 1.5 hours / not suitable for dogs

In previous years this walk, led by local expert Tim Ryan, has looked at hidden Chepstow below the Town Arch. This year we venture south and discover the rich history of the town above the Arch. This is an anecdotal walk with previously unheard stories and much much more. The walk ends with a visit to meet the team at Chepstow Community Fridge.

CWF26 walk 12 - Spring Woodlands around Devauden

Saturday 11 April / 10:00 start / 5.8 miles moderate / allow 3-4 hours / suitable for well-behaved dogs

This is a magical walk through green and mossy woodland, taking in Chepstow Park Woods, Fedw Wood and Ravensnest Wood as well as some long reaching views towards the Severn Estuary. A mixture of forest tracks, footpaths and quiet lanes.

CWF26 walk 13 - Woodlands and The Dean Farm Trust

Saturday 11 April / 14:00 start / 5 miles moderate with several stiles / allow 3 hours / not suitable for dogs

Dean Farm Trust is an organisation that helps to raise awareness for the welfare and fair treatment of animals. This is a unique opportunity to visit the sanctuary, meet some of the animals and hear a talk on the work of the Trust. The walk starts in the lovely Great Barnets Wood, meanders towards Shirenewton to visit the sanctuary, then returns to the start point via St Pierre Wood and the charming village of Mounton.

CWF26 walk 14 - Penallt, Meadows and Riverbank

Saturday 11 April / 14:00 start / 5.5 miles moderate with several steep slopes / allow 3 hours / not suitable for dogs

Penalt is situated in the Wye Valley National Landscape & comes from Welsh meaning “head” or “top of the wooded hill”, which still makes sense when viewed from the river, despite much of the land now being agricultural. The route passes through Pentwyn Farm SSSI, managed by the Gwent Wildlife Trust and one of Gwent’s largest flower rich meadows. From there, the walk drops down to the River Wye and the popular Boat Inn. We return through woodland passing The Argoed, a house with an interesting history, before returning to the starting point and the opportunity to purchase refreshments at The Bush at Penallt, kindly arranged by new owners Rowley and Jessica.

PROGRAMME - SUNDAY 12 APRIL

CWF26 walk 15 - Penhow and Magor Circular Trig Point Walk

Sunday 12 April / 10:00 start / 6.5 miles moderate / allow 3-4 hours / not suitable for dogs

This walk follows the St Brides brook south from Penhow visiting the beautiful church at St Brides and taking in some lovely meadows and rolling countryside. The route continues across fields and quiet lanes to Landevaud before climbing steadily to the trig point with some long reaching views of the countryside and Severn Estuary. The return leg passes through Penhow Woodlands National Nature Reserve and fields to Penhow Castle and Church.

CWF26 walk 16 - St Arvans Roundabout

Sunday 12 April / 10:00 start / 5.5 miles moderate with some stiles, ascent and descent / allow 3-4 hours / not suitable for dogs

There are several walks that can’t be left out of the festival. This route never fails to please, with a walk through picturesque Piercefield Woods, the remote church of Penterry and Gaer Hill with its spectacular views over the Estuary.

CWF26 walk 17 - Loysey and Croes Robert Woods

Sunday 12 April / 10:00 start / 5.5 miles moderate with some stiles, ascent and descent / allow 3-4 hours / not suitable for dogs

This circular walk takes in Loysey Wood and some little walked tracks, paths, open fields and quiet lanes, rewarded with some long reaching beautiful Monmouthshire views and hopefully spring flowers starting to bloom.

CWF26 walk 18 - Shirenewton Meander

Sunday 12 April / 10:00 start / 7.5 miles moderate with several stiles / allow 4-5 hours / not suitable for dogs

This walk explores the lesser-known footpaths around the pretty village of Shirenewton. Expect fabulous views to the Severn Estuary and Monmouthshire countryside, the remains of a castle, hidden valleys once part of Shirenewton Golf Course, old drovers roads and the delightful Mounton Brook, once home to paper mills.

CWF26 walk 19 - Hanley Farm Circular

Sunday 12 April / 10:00 start / 6.5 miles moderate with some stiles, ascent and descent / allow 3-4 hours / not suitable for dogs

This circular route is through rich pasture and flower filled woods with amazing views over the Severn Estuary, not often walked and a very interesting backdrop of Gloucestershire countryside taking in a section of the Gloucestershire Way.

CWF26 walk 20 - Llansoy and Wolvesnewton Three Churches Walk

Sunday 12 April / 10:00 start / 7.5 miles moderate with many stiles and some uphill sections / allow 4.5 hours / not suitable for dogs

A lovely circular walk exploring the open countryside in a lesser walked area of Monmouthshire. The route starts at the Star Inn and meanders through fields and past streams to the church at Llansoy, then onto Llangwm taking in some fabulous Monmouthshire views. The return leg is via the churches at Wolvesnewton and the small, pretty church of St Michael at Tor-Y-Myndd.

CWF26 walk 21 - Inspired by The Wye - Artist Walk and Exhibition

Sunday 12 April / 10:45 start / 5.5 miles moderate / allow 4 hours / not suitable for dogs

Join Wye Valley artist Lucy Burden, and Ruth Waycott from the Wye Valley National Landscape Team, for this walk through the landscapes which have inspired artists since the days of the Picturesque Wye Tour. Taking in the stunning Eagle’s Nest viewpoint and the Piercefield estate, the walk will finish at Chepstow Museum to visit ‘Flow/Liff’, Lucy’s exhibition of paintings inspired by the River Wye.

Acknowledgements

Chepstow Walking Festival is a community event and would not take place without support from many individuals who contribute to what has become an established feature of Chepstow's calendar. Key amongst these are our walk leaders, local experts and organisers who contribute time and skills entirely voluntarily, plus all those who take part. Thank you all!

It would take a whole page to list the contribution of local firms and organisations in making Chepstow Walking Festival a success. Many businesses do this by advertising their walker-friendly services through our 'stay, eat and shop' listings (please give them a try), and we also receive lots of financial, direct or indirect support with the Festival itself. Here is a list of organisations and individuals who will be helping us to deliver the Festival:

Terms and Conditions - the small print

The number of places on each walk is limited to ensure safety and the enjoyment of those participating. Walk places will be accepted on a 'first booked' basis, which means that the booking form and payment have been received by Chepstow Walkers are Welcome or a completed booking has been made online via Ticketsource. Walk and event tickets are non-transferable, and all children under 16 must be accompanied by a parent or responsible adult. Walkers must check they are capable of undertaking selected walks and must be suitably dressed for the weather and underfoot conditions - many walks will cross stiles - the walk description will advise where there are many stiles or particular obstacles to navigate.. Some of our walks are designed with dogs in mind, please do not bring dogs unless this is the case (see individual walk details). In the event a ticket cannot be used, Chepstow Walkers are Welcome will attempt to provide a place on a suitable alternative walk during the Walking Festival (subject to availability). All walks and events will commence at the advertised time, please ensure you arrive at the meeting location in good time. If at any time you need to get in touch with Chepstow Walkers are Welcome please use one of the contact options at the foot of this page. Please check www.walksinchepstow.co.uk for the latest Festival programme information. Any personal information provided on the booking form will be used solely for the purpose of administering Chepstow Walking Festival walks and events and will not be used for any other purpose, nor will this information be passed to any third party.