Chepstow Walks & Walking Routes | WalkingRambler

Wales · Monmouthshire · Wales

Walks from Chepstow, Monmouthshire

📍 Wales
🌿 Wooded river gorge, limestone cliff, estuary, ancient earthwork
0 routes available
⛰ Easy to Moderate
Free to access

🥾0 RoutesAvailable
Easy to ModerateDifficulty
📅Year-roundBest Months
🚗ChepstowStart Point

Chepstow is the starting point of Offa’s Dyke Path — at 177 miles the longest national trail in Britain — and sits at the point where the River Wye meets the Severn Estuary beneath one of the finest Norman castles in Wales. The Wye Valley Walk also begins here, heading north through the gorge towards Tintern and beyond.

An excellent small town with a magnificent castle and good rail connections from Cardiff and Bristol, Chepstow is the natural starting point for Offa’s Dyke and a superb base for the lower Wye Valley — one of the most beautiful landscapes in southern Britain.

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0 Walks from Chepstow

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Kingley Vale around the Nature Reserve, West Sussex

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Winchester via St Catherines Hill, Hampshire

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Winchester via Chilcomb and River Itchen

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Hindhead Devils Punch Bowl – 4.8 Mile Circular Walk

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Todenham Circular, Gloucestershire

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Cley next the Sea via Salthouse Norfolk – 9.1 Mile Circular Walk

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Waxham via Sea Palling & Horsey Gap Norfolk – 7 Mile Circular Walk

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Horsey Mere Norfolk – 3.7 Mile Circular Walk

Colyton
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Colyton via Whitford – 5.9 Mile Circular Walk

England
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Midhust via Cowdray Estate West Sussex

Chichester
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Chichester Via Canal and Harbour

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Meltham ~ Netherthong Circular 7 Miles

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Walk With Niamh

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Walk With Niamh

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Lister Park And Heaton Woods Sponsored Walk

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Walk Up South Loftus

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Keighley To Gargrave

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Ogden Loop 6m

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Ilkley To Leeds via Dales Way

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Ilkley To Leeds

At a Glance

Walks available0 routes
DifficultyEasy to Moderate
Best monthsYear-round
TerrainWooded river gorge, limestone cliff, estuary, ancient earthwork
CountyMonmouthshire
Dogs welcome✓ Yes

Getting There

📍
Chepstow, Monmouthshire
Open in Google Maps

Town car parks. Chepstow station (Cardiff–Gloucester line)

Food & Drink

The Boat Inn, The Three Tuns, La Siciliana

Notable Walks Nearby

  • Offa’s Dyke first day to Monmouth
  • Wye Valley Walk to Tintern
  • Devil’s Pulpit from Chepstow
  • Lancaut Peninsula loop
  • Chepstow racecourse circular
  • St Arvans & Piercefield
  • All Monmouthshire towns →

🗺 OS Map Reference

Walking around Chepstow is covered by OS OL14 / Explorer 167. Recommended for all routes in this area.

View OS Map Guide

Long Distance Trails Nearby

  • Offa’s Dyke Path
  • Wye Valley Walk

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