Pilgrims Way Challenge 2024 (SOLD OUT)

Saturday 15 June 2024

The Pilgrims Way Challenge is back on Saturday 15 June 2024 and now back to front! 

New for 2024, we have reversed (and tweaked) the routes, allowing first-timers and returning participants to enjoy fresh challenges and new vantage points along the way. 

Mid-May Update: Please note that due to popular demand, the event has now sold out! On the day entry will NOT be available.

Please view the Pilgrims Way Challenge Pre-Event Information

Lace up your walking boots, or running shoes, and enjoy the rural beauty of one of England’s oldest and least-trodden national trails. Now, starting from the coastal town of Dover, beneath the imposing walls of Dover Castle at Connaught Park, follow the North Downs Way through rolling fields and charming villages to the historic cathedral city of Canterbury. Then, onward via the Pilgrims Way and scenic Stour Valley to finish in the picturesque village of Wye, nestled in the Kent Downs Area of Outstanding Natural Beauty. Along the way, you’ll pass through ancient woodland, orchards, and fields, as well as a few challenging climbs encompassing the undulating geography of the Garden of England.

Photos from the Pilgrims Way Challenge 2023 can be viewed in our Facebook gallery here.

The routes

With three distances to choose from, the Pilgrims Way Challenge is perfect for people of varying fitness levels.

Stroll through a charming village of oast houses and period cottages, and soak in an immense sky while surrounded by endless green fields. Rolling hillside views, quiet country lanes, historic buildings and ancient woodland all await you. Walking, or running, the Pilgrims Way between Dover and Wye really has it all.

  • Canterbury – Wye: 25km (15.5 miles) – sign in between 10am-11am – View map
    From the historic city of Canterbury, your trail leads west through a nature reserve, and extensive orchards towards the rather intriguingly named Old Wives Lees. Then, descend to cross the valley to the pretty hilltop village of Chilham, with its ancient, timber-framed houses. From here, the next few miles are dominated by King’s Wood, where pilgrims banded together as protection against robbers. Finally, you’ll descend into rolling farmland, leading to the finish in the picturesque village of Wye. Total elevation gain: 320m

  • Dover – Canterbury: 35km – SOLD OUT (21.7 miles) – sign in between 8.30am- 9.30am – View map
    Beginning in Connaught Park, set beneath the imposing walls of Dover Castle, your path will follow an old Roman road that ran between Dover and Richborough, before passing the grand Waldershare House and its impressive mews. The route then leads through rolling fields to Womenswold, before passing the farming villages of Patrixbourne and Hode. Finally, you’ll catch a glimpse of Canterbury’s magnificent cathedral as you push on into the city’s cobbled streets towards the finish line. Total elevation gain: 290m

  • Dover – Canterbury – Wye: 55km – SOLD OUT (34 miles) – sign in between 7.30am-8.30am – View map 
    Take on the ultimate test of endurance and enjoy both sections of the Pilgrims Way described above in one day! After leaving Dover in the morning and experiencing all the natural beauty east Kent has to offer throughout the day, arriving at the charming village of Wye, your final destination, will be a welcome sight. Total elevation gain: 569m

What’s on offer?

This fully supported event includes:

  • Posted pre-event pack
  • Event technical T-shirt
  • Regular rest stops with drinks and snacks
  • Fully signed route
  • Free event app with live position tracking
  • Event medical support
  • Recovery vehicles
  • Finisher medal

Entry also includes food at the Canterbury hospice (for 35km and 55km hikers) and at the Wye Village Hall finish (for 25 and 55km hikers). 

It’s tough but achievable; with some training and determination, anyone can conquer the Pilgrims Way Challenge. Take on the hike with family, friends or colleagues, and make more friends along the way! When the welcome sight of the finish line comes into view, you’ll be rewarded with a finisher’s medal and a huge sense of achievement.


Mid-May Update: Please note that due to popular demand, the event has now sold out! On the day entry will NOT be available.

A maximum of 750 participants can take part in the Pilgrims Way Challenge 2024, so early registration is advised to avoid disappointment.

If capacity is reached before the event, on the day entry will not be available.

  • Early Bird Entry: £35 (closed 21 April 2024)
  • Standard Entry: £40 (closed 21 May 2024) 

You must be at least 16 years of age to participate in the Pilgrims Way Challenge and walkers under the age of 18 must be accompanied by a participating adult.

Please note that participant packs will be sent to all those who sign up before 27 May 2024. On the day entries will collect their participant number at the event.

Download the award-winning Pilgrims Event App for free

We’re proud to offer the Pilgrims Event App, available for iOS and Android devices. It’s free to download from the App Store and Google Play and is the perfect companion to enhance your Pilgrims event experience. Keep your training on track by recording your training activities and liking and commenting on your teammates. Receive up-to-date event information, view detailed route maps, earn in-app achievements and link your JustGiving page to see how your fundraising is going, all in one place.

Kit list and essential items

We’ve put together a full list of recommended equipment to make your hike a comfortable and safe experience. From clothing and footwear to some items that are essential, particularly for 55km walkers.

View the Pilgrims Way Challenge Equipment List

Get hiking fit with our training plans

We’ve put together 6/7 week training plans for each challenge distance to help get you hiking fit. The more you prepare yourself ahead of your challenge, the more you’ll enjoy the experience on the big day. Check out the Pilgrims Way Challenge training plans here.

Transport links

We recommend that you’re dropped off or met by family or friends who can take you home after such a tiring challenge. However, if you’re relying on public transport to get to and/or from the event, these transport links may be useful:

  • Dover: Serviced by trains running approx. every 30 minutes into Dover Priory Station from the directions of both Ashford and Canterbury. The start venue is 20-minute walk from the station.
  • Canterbury: Serviced by trains running approx. every 30 minutes into Canterbury West Station from the directions of Ashford, and Thanet. The start venue is 15-minute walk from the station. Trains run from Canterbury East Station back to Dover departing every 30 minutes
  • Wye: Serviced by trains running approx. every hour in the directions of Canterbury and Dover (via Ashford); the station is a 2-minute walk from the finish venue at Wye Village Hall and the last train of the night is 10:56pm toward Canterbury, and 11:20pm toward Dover (via Ashford).


Address information

Connaught Park,
Connaught Street,

City: Dover,

Postcode: Ct16 1HB

Contact information

Email: fundraising@pilgrimshospices.org

Phone: 01227 782062