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Guided walks

Guided hiking (and mountain biking) adventures in the area can be booked through Treads and Trails and guided walking holidays can be booked through Celtic Trails and Great British Walks. There's also plenty of shorter guided walks on offer, including the annual Chepstow Walking Festival every April, and two free guided walks from MonLife Countryside each month.

Inspiration

Countryside Guided Walks

Monmouthshire & Wye Valley guided walks with MonLife Countryside
Chepstow Walking Festival

Join Chepstow Walkers are Welcome for 6 days of walking fun at the annual Chepstow Walking Festival, held 7th -12th April 2026.
1. 7th Apr 202612th Apr 2026
Celtic Trails - Wye Valley Walk

Celtic Trails want to give you the best walking holiday in Britain you can have. Your walking holiday will take you along the very best of National Trails and Long-Distance paths through Wales.
Celtic Trails Walking - Offas Dyke Path

Celtic Trails want to give you the best walking holiday in Britain you can have. Your walking holiday will take you along the very best of National Trails and Long-Distance paths through Wales

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