Chepstow Autumn Walking Festival 2026
There is something particularly inviting about an autumn walk. The air feels fresher, leaves gather along the paths, and a flask of tea becomes a small pleasure worth stopping for. Around the Wye Valley and Forest of Dean, the changing season brings another reason to pull on your boots and spend a little longer outdoors.
Taking place from 23 to 25 October 2026, the Chepstow Autumn Walking Festival offers three days of guided walks exploring the surrounding countryside. With 21 walks on the programme, it is a lovely opportunity to discover unfamiliar paths and turn a day out into a leisurely autumn break.
Discover More Along the Way
A guided walk can reveal things that are easy to miss when exploring alone: the story behind a landmark, a feature in the landscape or the significance of an otherwise ordinary-looking path.
This year’s festival includes walks exploring local history, wildlife, geology and local producers, alongside opportunities to visit trig points. Adult tickets cost £5 per walk, while under-16s can join free. The festival also has fringe talks covering witchcraft and pilgrimage, adding another dimension to the weekend.
Rather than choosing solely by distance, look for a subject that catches your interest. A walk with a historical theme might introduce you to somewhere you would never have thought to visit, while a wildlife-focused outing offers a reason to slow down and look more closely.
The autumn programme is open for bookings through Chepstow Walkers are Welcome. Check individual listings for distances, terrain, starting points and any requirements before choosing your walks.
Leave Time for the Forest of Dean
The festival is a good starting point for a wider visit to the area. If your plans allow, keep an extra day free to explore the Forest of Dean at your own pace.
There is no need to fill every hour. A woodland walk, somewhere pleasant to stop for lunch and a little time beside the water can be quite enough.
Take in the View at Symonds Yat Rock
For a memorable autumn outlook, consider Symonds Yat Rock. The viewpoint looks across the River Wye and surrounding landscape, while walking trails offer opportunities to explore the woodland beyond. It is a rewarding place to pause with a camera or simply watch the changing light over the valley.
Check Forestry England’s latest visitor information before setting out, particularly if your chosen route involves connecting paths or bridges.
Enjoy a Quieter Moment at Mallards Pike
Mallards Pike offers a lakeside setting for an autumn outing in the Forest of Dean. It makes an appealing addition to a walking break, especially when you would like time by the water between more energetic days.
Pause by Cannop Ponds
Another option is Cannop Ponds, where the waterside setting provides opportunities to watch local birdlife. Bring binoculars if you have them, and leave yourself time to sit quietly rather than moving straight on to the next stop.
Make It an Autumn Stay
A walking weekend feels different when there is no long journey home waiting at the end of the day. Staying for a few nights leaves room for a festival walk, an independent forest outing and an evening spent putting your feet up.
For couples planning a wider countryside break, The Queen Bee Cabin in Much Birch, South Herefordshire, offers a peaceful place to return to. With a king-size bed, kitchen facilities and a bathroom with a shower, it lends itself to unhurried mornings and comfortable evenings after a day outdoors.
Plan your journeys from the cabin to each festival meeting point, then leave some space in the itinerary for discoveries along the way. You can check availability for an autumn stay once you have chosen your walks.
A Little Preparation Goes a Long Way
Pack comfortable walking boots, waterproofs, warm layers, water and something to eat. Check the forecast and your walk’s instructions, and allow enough time to reach the meeting point without rushing.
Above all, resist the temptation to squeeze too much into the weekend. The pleasure of an autumn walking break lies partly in having time to notice things: leaves reflected in still water, a view opening between the trees, or a conversation that continues long after the walk has finished.
The Chepstow Autumn Walking Festival provides the occasion. A few extra days in the countryside give you the chance to enjoy everything around it.