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© 2026 Celtic Trails Walking Holidays. A company registered in England and Wales under number 07736096. All rights reserved. Registered address 5 Ashweir Court, Tintern, Wales, NP16 6SE United Kingdom.

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Walking Holidays
About Us
Back to walkGilpin Trail
ItineraryWVW-GIL2
View of the Wye valley from Eagle's Nest point

WVW-GIL2 · Gilpin Trail · Wales

Ross on Wye to Chepstow

Difficulty
Easy to Moderate
Distance
40.2 miles
Walking
5 Days
Bed & Breakfast
6 Nights
Grade
Classic
Dog Friendly
No

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From £765 per person
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Overview

  1. Day
    1
    Arrival Day
    1. Ross on WyeRoss on Wye

    Arrival and overnight at your accommodation in Ross-on-Wye.

  2. Day
    2
    Ross on Wye to Kerne Bridge
    5.5 mi · 8.9 km
    1. Ross on Wye to Kerne Bridge
    2. Kerne BridgeKerne Bridge

    Your route climbs up Chase Hill to lead you out of Ross, making its way around the wooded valleys and meadows of Leys and Howle Hill. The Wye Valley is distinguished by the thick layers of bluebells that line its woodland trails and tracks through meadows, and this section should be a great chance to catch sight of the flowers of the forest as you follow an undulating path down to Kerne Bridge village.

  3. Day
    3
    Kerne Bridge to Symonds Yat
    11.7 mi · 18.8 km
    1. Kerne Bridge to Symonds Yat
    2. Symonds YatSymonds Yat

    Following the bridge out of the village, the route follows the river as it meanders through the upper Wye gorge south towards the Welsh border. You’ll pass the community of Lower Lydbrook as well as the old church at the village of Welsh Bicknor on your route, crossing a disused railway bridge to the other side of the Wye’s banks. From here, you’ll catch your first glimpse of the distinctive Symonds Yat viewpoint, once the site of an Iron Age fort, as you follow the route around the riverbend to Symonds Yat village and your stay for the night.

  4. Day
    4
    Symonds Yat to Redbrook
    8.2 mi · 13.2 km
    1. Symonds Yat to Redbrook
    2. transfer
    3. MonmouthMonmouth

    Leaving the village, the route follows a woodland path towards Biblins Bridge, which takes you over and through fields before re-joining the riverside track towards Wales. The route then takes you over stiles and through fields towards Monmouth and over the Welsh border. From here, a narrow footbridge takes you over a stream where the town of Monmouth comes into view, where the route leads past the rowing club, taking you over the bridge and back alongside the river. From here, your route takes you through kissing gates and fields, along a gentle meadow walk that leads you almost directly into the Redbrook as you pass over a stile and follow the path into the village.

  5. Day
    5
    Redbrook to Tintern WVW
    8.8 mi · 14.2 km
    1. transfer
    2. Redbrook to Tintern WVW
    3. TinternTintern

    Today marks one of the more strenuous sections of this route, however, these steeper sections are rewarded with some stunning viewpoints over the Wye river valley. Your route begins with a short walk through a meadow alongside the river, which tapers off onto a track into Hael Wood. Turn along the road towards Whitebrook, making a steeper ascent with fantastic views on your left as the footpath eventually levels out and continues straight ahead. Your path then branches off into a woodland bridle path, passing the village of Llandogo and then along the bridge over Cleddon falls, eventually joining the road to take you past the Old Tintern Railway Station through woodland and then back alongside the river and over footbridges into Tintern village.

  6. Day
    6
    Tintern to Chepstow
    6 mi · 9.7 km
    1. Tintern to Chepstow
    2. ChepstowChepstow

    Your route leads past Tintern Abbey along a small road that eventually narrows into a woodland path through Limekiln Wood. Here, the path starts to incline as you walk parallel to a stream, turning off over a footbridge. Walk up the steps, bringing you across a field and over stiles to Blackcliff Wood. Continuing along the ridge as the path twists and turns, you’ll cross paths with the Eagle’s Nest viewpoint, with spectacular views right across the Severn and Wye valleys, as well as the twin Severn Bridges. From here, the path cleaves its way through Piercefield Wood, where, skirting along the edges of Chepstow Racecourse, your route eventually tumbles out at Chepstow Castle leading you to the end of your route.

  7. Day
    7
    Day 7

    Departure from Chepstow following breakfast.

Overnight locations and transfer arrangements may differ slightly from those shown, depending on availability.

What's Included

  • Good standard accommodation at a mixture of guesthouses, farmhouses, local inns and B&Bs with en-suite or private facilities wherever possible
  • Breakfast
  • Luggage transfers
  • Personal transfer between accommodation and path that form a part of our standard package
  • Route planning
  • Walk pack including Trail Guide and mapping, itinerary, accommodation directions and route notes, lunch and dinner information, restaurant recommendations and holiday planning details

Extras

Rest days/additional nights:

  • Prices from £150 per room per night

Upgrade options:

  • Speak to our team to discuss upgrade options for this itinerary

Supplements:

  • Short notice bookings and Bank Holidays may incur additional charges

Walk Pack postage:

  • to UK: included in price
  • to Europe: £25 per pack
  • to Rest of World: £30 per pack

Extra Walk Packs:

  • Please see here for full details and supplements

From Pricing

Plan your trip

1 Jan 2026 – 31 Dec 2026

£765pp

Per person, based on two people sharing

Solo traveller
£1,263
Single occupancy
£1,065
Rest days£150per room, per day
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