Head to Wales in April and October to discover the amazing countryside during the Chepstow Walking Festival.
The Chepstow Walking Festival, established in 2014, is a highly anticipated annual event that features many guided walks.
The festival aims to highlight the amazing scenery, local food producers, and the rich history of the Wye Valley National Landscape, Monmouthshire, and its surrounding areas. With such a varied and picturesque landscape, the toughest choice lies in selecting which walks to showcase, enticing visitors to explore our hidden treasures, stunning vistas, ancient woodlands, charming villages, historic churches and grand rivers, among other attractions.
Chepstow is renowned for its extensive waymarked trails, serving as the start or finish point for Offa’s Dyke Path, Wye Valley Walk, Gloucestershire Way and the Wales Coast Path. It is a fully accredited ‘Walkers are Welcome’ town, joining a network of towns that truly live up to that welcoming promise.
Chepstow Walking Festival 2026
There will be 21 guided walks. Whether you’re a keen walker, a local history enthusiast, a wildlife lover, a trig-point bagger, or simply looking for a great way to enjoy the autumn countryside, there’s something for everyone.
Festival Fringe Events
The festival will host two speakers:
Dr Tabitha Stanmore – Witchcraft and the Role of Cunning Folk
Philip Averay – A Pilgrimage from Chepstow to Rome
When Is the Chepstow Walking Festival 2026?
This year the festival is split between Spring and Autumn with the first session running from 10 to 12 April 2026 and the second from 23-25 October.
How Much Does It Cost?
Tickets cost £5 per adult. Under 16s go for free with accompanying adult. Booking essential.
If you can not make this Welsh walking festival, you might wish to pop across the border to the Herefordshire Walking Festival held in June.
Image supplied by the organisers.
