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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-GIL1
View of the Wye valley from Eagle's Nest point

WVW-GIL1 · Gilpin Trail · Wales

Ross on Wye to Chepstow

Difficulty
Moderate
Distance
39.9 miles
Walking
3 Days
Bed & Breakfast
4 Nights
Grade
Classic
Dog Friendly
No

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From £545 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 Symonds Yat
    15.6 mi · 25.1 km
    1. Ross on Wye to Symonds Yat
    2. Symonds YatSymonds Yat

    Ahead of you, you have a day of delightful riverside walking following the Wye as it meanders through the upper Wye gorge as well as more challenging sections with some steep climbs leading out of Ross-on-Wye and past Kerne Bridge through woodland and field. After making the ascent up Chase Hill to leave Ross, the route snakes its way around hills, meadows and trees with some challenging climbs en-route. From Kerne Bridge, there is a sudden change of pace, as your route begins to steer a close course to the river, taking you along the riverbank past Welsh Bicknor to Symonds Yat.

  3. Day
    3
    Symonds Yat to Llandogo
    13.8 mi · 22.2 km
    1. Symonds Yat to Llandogo
    2. transfer
    3. TinternTintern

    Today’s route takes you over the border and back again several times, as you follow the Wye’s course between Wales and England. You’ll pass the Seven Sisters Rocks, a Victorian limestone quarry that lies on one side of the track while you have the river running alongside you on the other.

  4. Day
    4
    Llandogo to Chepstow
    10.5 mi · 16.9 km
    1. transfer
    2. Llandogo to Chepstow
    3. ChepstowChepstow

    The last day of your walk features some of the Wye Valley’s more challenging sections as the route undulates quite steeply up and back down around the valley. However, these steep climbs are rewarded with some of the most distinctive and unforgettable viewpoints found in this part of the world, as you stop to take pause and appreciate the panorama over the river valley. The 12th century Tintern Abbey cuts an impressive figure in the distance on the approach to the village, where you then join a woodland trail out of the village passing beneath the Black Cliffs and re-joining the river at Lover’s Leap to follow the route into Chepstow town.

  5. Day
    5
    Day 5

    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

£545pp

Per person, based on two people sharing

Solo traveller
£865
Single occupancy
£725
Rest days£150per room, per day
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