View of the Wye valley from Eagle's Nest point

WVW-GIL2

Ross on Wye to Chepstow

Difficulty
Easy to Moderate
Distance
40.2 miles
Walking
5 Days
Bed & Breakfast
6 Nights
Grade
Classic
From £765 per person
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Itinerary Details

Day 1Arrival Day

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

  1. AccommodationRoss on Wye
Day 25.5 miles (8.9 km)

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.

  1. Ross on Wye to Kerne Bridge

  2. AccommodationKerne Bridge
Day 311.7 miles (18.8 km)

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.

  1. Kerne Bridge to Symonds Yat

  2. AccommodationSymonds Yat
Day 48.2 miles (13.2 km)

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.

  1. Symonds Yat to Redbrook

  2. transfer
  3. AccommodationMonmouth
Day 58.8 miles (14.2 km)

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.

  1. transfer
  2. Redbrook to Tintern WVW

  3. AccommodationTintern
Day 66 miles (9.7 km)

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.

  1. Tintern to Chepstow

  2. AccommodationChepstow
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 £75 per person per night.

    Upgrade options: Speak to our team to discuss upgrade options for this itinerary.

    Walk Pack postage: Europe - to first night’s accommodation, Rest of World - £30 supplement, (UK is included in price).

    Extra Walk Packs: can be requested, please see here for full details and supplements.

    Bank Holidays and short notice bookings may incur extra charges.

    Pricing

    Jan 1, 2026Dec 31, 2026

    £765

    Per Person (Based on 2 people sharing)

    £1263 Solo Traveller

    £1065 Single Occupancy

    £75 Rest Days (Per person per day)