Chepstow Autumn Walking Festival

Friday 23rd–Sunday 25th October 2026

Put your best foot forward this autumn! Autumn is a wonderful time to explore the countryside around Chepstow, and this year’s Chepstow Autumn Walking Festival invites you to discover the Lower Wye Valley, Monmouthshire and the Forest of Dean on foot.

21 guided walks,  wrapped up in one long weekend, will take you through some of the area’s most beautiful and fascinating landscapes. Enjoy autumn colours, wildlife and geology, and uncover stories of local history and heritage, visit local producers and even bag a trig point along the way or go on a night walk for a different experience.

Whether you’re an experienced walker or simply enjoy getting out and exploring somewhere new, the festival offers a great opportunity to see the area from a different perspective, meet like-minded people and enjoy the spectacular autumn countryside.

Alongside the walks, the festival will also feature a programme of fringe events. We are delighted to welcome two fascinating speakers as part of this year’s festival.

Friday 23rd October Dr Tabitha Stanmore – Witchcraft and the Role of Cunning Folk

Join Dr Tabitha Stanmore, social historian of magic and witchcraft at the University of Exeter, for a fascinating exploration of witchcraft and the role played by cunning folk in our past.

Saturday 24th October Philip Averay – A Pilgrimage from Chepstow to Rome

Hear from Philip Averay, Vicar of St Mary’s Priory, Chepstow, about his remarkable 1,500-mile pilgrimage on foot from Chepstow to Rome, relying on the kindness and goodwill of people along the way.

Adult festival tickets are £5 per walk, with under 16s walking free.For booking and full programme please visit www.walksinchepstow.co.uk/walking-festival.