The Route
The Pilgrims Way Challenge follows the ancient pilgrim route from Dover to Canterbury — the same path trodden by medieval pilgrims heading to the shrine of Thomas Becket at Canterbury Cathedral. The 21.7-mile (35km) route traces Roman roads and well-established footpaths through open farmland, estate parkland and picturesque East Kent villages, with a longer 34-mile option for the truly dedicated extending all the way to Wye.
Starting in Dover, the route heads inland through the rolling chalk downland of East Kent, passing through some wonderfully varied landscapes — wide open arable fields with huge skies, ancient woodland tracks, and the manicured grounds of historic country estates. The North Downs scenery is some of the best walking Kent has to offer, and the June sunshine made it particularly special.
Highlights Along the Way
Waldershare Park
One of the absolute highlights of the route is passing through the grounds of Waldershare Park — a stunning early 18th century baroque country house set in sweeping parkland. Walking across the open grassland with this magnificent building as your backdrop is genuinely breathtaking, and a reminder of the extraordinary hidden gems tucked away across East Kent. The estate has belonged to the Montagu family for generations and the house, built around 1712, is a Grade I listed building.
The Village of Patrixbourne
The route passes through Patrixbourne, one of East Kent's most beautiful villages, with its Norman church of St Mary the Virgin featuring an exceptional carved Romanesque doorway — worth stopping to appreciate even when your legs are telling you to keep moving. The Nailbourne stream, which flows intermittently through the valley, was still running in June, adding to the pastoral charm of this stretch.
Church Rest Stops
One of the really well-thought-out elements of the challenge is the church rest stops along the route, staffed by Pilgrims Hospices volunteers and staff. Each one was a warm, welcoming haven — cold drinks, snacks, and a chance to rest your feet in centuries-old surroundings. The volunteer support throughout was outstanding, and you could really feel the community spirit behind the event.
The Route Stage by Stage
Dover — Start
Assembly and briefing. The journey to Canterbury begins on Roman roads heading northwest out of Dover through the chalk downland.
Waldershare Park (~mile 5)
First major highlight — crossing the parkland of the stunning 18th century Waldershare House. First rest stop church in the area.
Shepherdswell (~mile 8)
Through the village of Shepherdswell — almost past my front door! Second church rest stop, halfway hydration check.
Patrixbourne (~mile 14)
One of Kent's most beautiful villages. The Nailbourne still in flow — a rare and welcome sight in a dry summer. Norman church rest stop.
Canterbury — Finish (~mile 21.7)
The medieval city comes into view. 6.5 hours after leaving Dover, the finish line and a well-earned medal.
The Cause — Pilgrims Hospices
Pilgrims Hospices provide compassionate, expert end-of-life care to people across East Kent, completely free of charge to patients and their families. They have three hospices — in Canterbury, Ashford and Margate — and care for around 2,500 patients each year. The annual Pilgrims Way Challenge is one of their flagship fundraising events, bringing together hundreds of walkers each June to raise vital funds for the charity.
The event raised tens of thousands of pounds in 2025, with participants ranging from first-timers completing their first ever charity walk to hardened adventurers taking on the extended 34-mile route to Wye. The atmosphere was genuinely uplifting — a wonderful mix of challenge, community and purpose.
Pilgrims Hospices provide free specialist palliative care to people with life-limiting illnesses across East Kent, supported entirely by fundraising and donations. The Pilgrims Way Challenge takes place each June.
pilgrimshospices.org · To take part in the 2026 challenge, register at pilgrimshospices.org/events
On the Day
Conditions were near perfect — warm and sunny with a light breeze. The open farmland sections across the chalk downland were glorious in the June light, with wildflower margins in full colour and the occasional red kite drifting overhead. The oast houses dotted along the route are quintessentially Kentish, and a few of the more scenic examples provided some of the best photo opportunities of the day.
Completing the route in 6.5 hours felt like a solid effort for 21.7 miles on a warm day. The church rest stops were genuinely essential — whoever planned the spacing of those deserves enormous credit. Crossing the finish line in Canterbury with hundreds of other walkers, medals in hand, was a genuinely moving experience. A brilliant event for an exceptional charity.
35km Challenge Complete
Dover to Canterbury · Participant #195 · June 2025 · 6.5 hours
Would I Do It Again?
Absolutely. The 2026 challenge is already in the diary. If you're based in East Kent and looking for a meaningful charity walking challenge with a brilliant atmosphere, brilliant cause and beautiful scenery — this is the one. Sign up early as places fill fast.
If you want to explore the Pilgrims Way independently outside of the challenge event, the route is well signed and walkable in sections. The stretch through Waldershare Park and down into the Nailbourne Valley is particularly worth doing as a standalone day walk from Shepherdswell or Barham.
📷 Pilgrims Way Challenge 2025 — In Photos
