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 views
  • Cross paths with picturesque towns and villages
  • Discover the romantic ruins of Tintern Abbey
  • Scenic walking in a protected AONB landscape providing a satisfying blend of woodland, riverside and hill walking
  • Steeped in history - follow in the footsteps of Gilpin's 1770 tour
  • Expert knowledge from our team based in the Wye Valley
📷Tintern Abbey in autumn The Wye Valley in Autumn

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. 

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 Symonds 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 £480 pp
    Ross on Wye to Chepstow
        4 nights, 3 days
    Ref: WVW-GIL1
    Grade: Classic

    or ask us a question
    What's Included:
    3 walking days
    4 nights
    4 breakfasts
    2024 Prices
    6 Nights, 5 Days
    from £685 pp
    Ross on Wye to Chepstow
        6 nights, 5 days
    Ref: WVW-GIL2
    Grade: Classic

    or ask us a question
    What's Included:
    5 walking days
    6 nights
    6 breakfasts
    2024 Prices
    • 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

    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 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.

    Landscape Appreciation on Gilpin’s Wye Tour Client Reviews

    4.7/5 based on 12 reviews
    Celtic Trails is service orientated and respond quickly to enquiries.
    - May 2024
    Celtic Trails were well organised 7 provided backup if needed. As complete beginners the information was comprehensive and invaluable. We saw a great variety of flora & fauna and are inspired to walk again in the future.
    - May 2024
    We loved hiking on the River Wye, off the beaten track and with beautiful scenery. We feel stronger and as a result now walk at least 6 miles a day.
    - May 2024
    Celtic Trails took care of us and picked a good route with cute little B&Bs. We had time to visit castles, abbeys, etc. not just hiking past.
    - April 2024
    Celtic Trails are very professional and very much on top of details.
    - March 2024
    Thorough and reliable.
    - September 2023
    Very easy to book holiday. Good information pre- departure.
    - August 2023
    I would recommend Celtic Trails. Well organized. Personal service. Efficient. Beautiful trail with excellent accommodations. We love adventure holidays! This trip was a trip of a lifetime! The trail was rigorous and absolutely beautiful.
    - July 2023
    Our experience with Celtic Trails was wonderful and I've already highly recommended them to many friends. I am also hoping to do another trip with Celtic Trails in the future.
    - June 2023
    An excellent experience with Celtic Trails - all staff always helpful both before and during the holiday. Would recommend.
    - May 2022
    Beautiful scenery. Lots of big hills.
    - May 2022
    Celtic Trails were very helpful. We would recommend them.
    - April 2022
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