4 to 6 nights
35 mls (km)
Welsh Borders
Easy to Moderate
Mar to Oct

Picturesque riverside walking in the spectacular Welsh Borders

  • Follow the The Wye Tour – the birthplace of British tourism and the term 'picturesque'
  • Gaze out over spectacular viewpoints
  • Cross paths with picturesque towns and villages
  • Discover the romantic ruins of Tintern Abbey
  • Scenic walking in a protected AONB landscape providing a fantastic blend of woodland, riverside and hill walking
  • 2020 celebrates the 250th anniversary of Gilpin's 1770 tour
  • Expert knowledge from our team based in the Wye Valley

Why this Walk?

In 1770 Rev. William Gilpin took a boat trip down the River Wye, sketchbook in hand, and eagerly pursued the British equivalent of the European Grand Tour.  A pioneer of the 'Picturesque' and the way we explore and appreciate landscape in Britain, his book ‘Observations on the River Wye’ was arguably the first tour guide to be published in Britain and became an essential item for Victorian travellers, poets and artists visiting the area; his guide recommended that tourists should “examine the face of a country by the rules of picturesque beauty”.

The 'Wye Tour' is acknowledged as the Birthplace of British Tourism; in 1745, a Rector by the name Dr. John Egerton began entertaining guests with trips down the Wye in a specially made boat. Inspired by the publications of Gilpin's guidebook, by the late 18th century there were at least 8 boats taking visitors along the tour.

Find out more about Gilpin's Wye Tour here and the 2020 Anniversary here.

Walking the Wye Tour provides a fantastic blend of hills, rivers, charming borders villages and the scenic route that connects them as you follow the course of the Wye downstream. The Wye Valley is designated a ‘Site of Scientific Interest and Special Area of Conservation’, highlighting what an inspiring place it is to visit and explore.

The AONB have created a great visitor guide which can be found here.

The Path

From Ross-on-Wye, your route leads you out of the town and southwards, up and over hills and fields and then alongside the river past Lydbrook and across Kerne Bridge to Welsh Bicknor. From here, the trail steers a close course to the river as you pass Symond’s Yat (once an Iron Age hillfort) and then back through hills, fields and woodland on your way past the town of Monmouth. From here, the route cleaves its way through the river valley on a route past Redbrook, Whitebrook and Llandogo which features some of the more stunning viewpoints found in this part of the world. Tintern Abbey is an impressive fixture of the landscape on your way into Tintern Village, where the route climbs back up through woods and into the Chepstow town.  Tintern Abbey was undoubtedly the most eagerly awaited view on the Wye Tour: “A more pleasing retreat could not easily be found”, wrote Gilpin in 1770.

Chepstow Castle on Gilpin's Wye Tour
Chepstow Castle features at the end of Gilpin's Wye Tour

The Accommodation

Our accommodation is hand-picked on the basis of feedback we receive from our walkers, and as such is often rotated based on this factor, as well as seasonal availability. Accommodation in the Wye Valley is typically very traditional in the way it presents itself, with most of the B&Bs, hotels and pubs we book in the area being converted from old rural buildings, all characterised by a consistently high standard of quality and service. Walkers can expect accommodation within close proximity of the river Wye, with breakfast included and a warm welcome waiting on arrival. Being based in the local area, we work closely with our accommodation providers along the route to ensure that our walkers can expect a tranquil and relaxing experience to follow a day spent out exploring the Wye Valley.

Our Landscape Appreciation on Gilpin’s Wye Tour Itineraries

  • Ross on Wye to Chepstow
    Distance: 34.5 miles (55.5km)
    4 Nights, 3 Days
    from £340 pp
    WVW-GIL1 ~ Ross on Wye to Chepstow ~ 4 / 3 classic
    • Day 1
      Arrive Ross on Wye

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

    • Day 2
      Ross on Wye to Symond’s Yat
      11.8 miles/18.8km

      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 Symond’s Yat.

    • Day 3
      Symond’s Yat to Llandogo
      12.3 miles/19.6km

      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.

    • Day 4
      Llandogo to Chepstow
      10.5 miles/16.8km

      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.

    • Day 5
      Depart Chepstow

      Departure from Chepstow following breakfast.

    or ask us a question
    What's Included:
    3 walking days
    4 nights accommodation
    4 breakfasts
    6 Nights, 5 Days
    from £495 pp
    WVW-GIL2 ~ Ross on Wye to Chepstow ~ 6 / 5 classic
    • Day 1
      Arrive Ross on Wye

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

    • Day 2
      Ross on Wye to Kerne Bridge
      5.5 miles/8.8km

      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.

    • Day 3
      Kerne Bridge to Symond’s Yat
      8 miles.12.5km

      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 Symond’s Yat viewpoint, once the site of an Iron Age fort, as you follow the route around the riverbend to Symond’s Yat village and your stay for the night.

    • Day 4
      Symond’s Yat to Redbrook
      8 miles/12.8km

      Leaving the village, the route follows a woodland path towards Biblin’s 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.

    • Day 5
      Redbrook to Tintern
      8.8 miles/14km

      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.

    • Day 6
      Tintern to Chepstow
      5.5 miles/8.8km

      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 by Chepstow Castle leading you to the end of your route.

    • Day 7
      Depart Chepstow

      Departure from Chepstow following breakfast.

    or ask us a question
    What's Included:
    5 walking days
    6 nights accommodation
    6 breakfasts
  • 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 where necessary, route planning, Walk Pack including route notes, OL14 Map, itinerary, accommodation directions, local interest leaflets and holiday planning.

    You choose which day you would like your holiday to start on. We will book your holiday in accordance with your requirements.

    Our Landscape Appreciation on Gilpin’s Wye Tour holidays are available to walk March to October.

    Public Transport Planners

    Rail: Railway stations are located in Chepstow. The nearest main train stations to Ross on Wye are at Hereford and Gloucester.

    Bus: Bus stations are located in Ross on Wye and Chepstow.

    Car: If you prefer to arrive by car we can advise on parking in Chepstow.


    Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs. Call one of our helpful team on +44 (0)1291 689774 or e-mail us here.
    Booking Request - Landscape Appreciation on Gilpin’s Wye Tour
    • Date Format: DD slash MM slash YYYY
    • This field is for validation purposes and should be left unchanged.
    What Happens Next?

    We will check your details and come back to you within two working days with a personalised estimate based on your requirements. We will then formally request a deposit of £150 per person (£100 per person for a single centre break) and book all your arrangements - find out about our full booking process here.

    Please note this does not constitute a booking confirmation, we kindly ask you to refrain from booking any travel until we have confirmed all your arrangements.

    Still Have Questions?

    If you are still unsure on any of your requirements, please do enquire with us first and one of our friendly team will be happy to help you with any queries you have.

    Enquire About Landscape Appreciation on Gilpin’s Wye Tour
    +44 (0)1291 689 774
    Our lines are open: 9am to 5pm (GMT), Monday to Friday
    Sample Accommodations

    Please note: exact accommodation booked will depend on availability.