The Pilgrims’ Way has two possible starting points: Southwark Cathedral in London or Winchester Cathedral. The two paths cross at Otford. I chose to walk from London as this is the route of Chaucer’s Canterbury Tales, as well as the way Becket himself traveled between the two cities.
This is the day by day, more practical experience of the journey. You can read/listen to my lessons learned from the way here.
Preparation and resources
I walk regularly so I was well-trained for a multi-day walk although I had never done six days solo before. I did a one-day navigation course to brush up on my map-reading skills, for which I was grateful. Check out my multi-day kit list here.
I used The Cicerone guide, Walking the Pilgrim’s Way by Leigh Hatts, which is excellent. I also carried OS Maps of the entire route. To reduce the amount of paper, I cut out the sections I needed and pulled out the section I needed each day.
My book, Pilgrimage, Lessons Learned from Solo Walking Three Ancient Ways, is out now.
As I walked, I followed the guidebook and the map, and in several places, I also used my mobile phone for Google Maps. This was particularly necessary for the more urban areas where the guidebook and OS Maps are not granular enough.
Day 1: Southwark Cathedral, London to Dartford (40.8km)
Some people split this day into two, but I wanted to get the urban section of London out of the way, so I visited Southwark Cathedral the day before and left in the dark to walk the A2, the busy Old Kent Road. It’s not the most romantic or scenic route, but it is authentic as it has been a major transport route since Roman times.
Keep an eye out for the surprising mural by Adam Kossowski at the turnoff to Peckham, now the site of the Everlasting Arms church. If I hadn’t been looking out for this, I would have missed it and it’s well worth stopping for. There is a quote from the Canterbury Tales and images of pilgrims.
There are toilets at the big Sainsburys at New Cross Station, or you can stop in cafes on the route. There are lots of interesting modern churches and multi-cultural shops as well as glimpses of ghost signs if you look up and evidence of once-beautiful architecture, but it’s mostly a gritty, urban walk for the first 20km.
The sky opens up as you cross Blackheath near Greenwich. Continue to Shooters Hill and Oxleas Woodlands, where you can leave the road and take a break. Just before the turn-off to the cafe, there are some waymarkers in the churchyard.
The Oxleas Woods Cafe is what’s known as a ‘greasy spoon cafe’ in England. Cheap and cheerful, tasty, no-fuss food like eggs and bacon and chips and a mug of builder’s tea (black tea with milk). There are also toilets on site.
Feeling refreshed after my lunch, I set off again!
Walk through the woods away from the cafe, and listen out for the wild parakeets of south London. The original birds escaped years ago and now you can see and hear them across the city. The rest of the day’s walk is mostly on the Green Chain. Keep an eye out for the signs.
The Green Chain path is obvious on the OS Map and it’s easy to navigate by the green shapes and signs. You have to veer off the highlighted route to get to the cafe. Don’t miss it as there’s not much else for a long time.
The ruins of Lesnes Abbey are the next place of interest, with a tea-room and toilets. There’s a view over London through the arches on the hill. It was founded in 1178 by a nobleman who helped Henry II to secure Becket as Archbishop. It was closed in 1525 by Cardinal Wolsey.
You finally emerge on the Thames bank at Erith. It’s quite urban and bleak in parts here.
When you walk through the Erith Industrial Estate, you might wonder if you are off track because it’s ugly and not really meant for walkers — but head towards the Erith Yacht Club and you’ll find the path again. I almost got the train here because it was so miserable and urban, but seriously, it’s worth continuing. Some walks are about the beauty of nature. This one is more about human history, which is messy and ugly in many parts.
But although it started badly, this was the most surprisingly beautiful part of the walk for me. After the grittiness of the city, you have this ancient salt marsh scenery on your left as you walk around the Crayford Ness headland and then follow the River Darent toward Dartford. The birdlife is incredibly varied and I walked this at dusk and sunset, so it was bathed in a golden light.
No photo can do justice to how I felt in this part of the walk. It was perhaps the contrast and the fact I was so tired, but I just loved this section. The thin line of the path has the urban, industrial waste park on one side, but it brings into stark focus how beautiful the marshes are.
I stayed at the Royal Victoria and Bull Hotel in the center of Dartford, which was basic but clean with decent food. It’s close to all amenities, shops, restaurants, etc. It’s also most likely to be Dartford’s oldest inn and was probably owned by Dartford Priory.
As I walked the route in October 2020 during the COVID19 pandemic, I wore a mask in all interior public areas and crowded places. This is me leaving the next morning. There are plenty of coffee shops and places to get food around here. There’s a street market on Saturday.
Day 2: Dartford to Kemsing (27.5km)
I was pretty stiff after the big day yesterday so this day felt much more relaxing!
Out of Dartford, you join the Darent Valley Path, which is a pleasant walk by the river for much of the day.
There are some pretty churches on the route. The lychgate of St Peter and St Paul, Shoreham, Kent, has the words, Blessed are the dead which die in the Lord, written over the arch.
There are lots of roads with ‘Pilgrim’ in the name as you walk.
This is a pretty rural day with plenty of fields. Here’s me walking through one of them!
Kent is famous for its apples, and there were lots of baskets left outside for people to take some from the gardens.
I stayed at Up the Downs B&B in Kemsing, which was welcoming and comfortable and near an excellent curry house for dinner with some little shops for re-stocking on supplies.
Day 3: Kemsing to Aylesford (34.1km)
It was beautiful walking out of Kemsing as the dawn broke, with horses in the mist and beautiful rolling countryside and hedgerows for much of the day. My mum grew up around here so I thought of her and my grandparents, who died years ago. It’s a relaxing stage of the walk.
This section joins the North Downs Way which you can follow all the way to Canterbury, but the Pilgrims’ Way guidebook veers off in sections to visit other places of interest.
The final stop for the day is The Friars at Aylesford. You get there by walking through a sewage works which I thought was in many ways an apt approach.
Sacred and profane. Physical and spiritual.
Remember to get your pilgrim stamp at the Priory office. There are also toilets and a cafe at the Priory.
During normal times, you can stay at the Aylesford Priory but it was closed to overnight visitors due to COVID19, so I stayed at the nearby Premier Inn, Maidstone Allington. The Premier Inn is my favorite UK budget hotel as they focus on a good night’s sleep and are always reasonably priced. If you think about the pilgrims from the Canterbury Tales, they would have stayed at basic inns and eaten basic food, so I tried to do the same.
If you do have to stay at the Premier Inn, I recommend getting a taxi there and back to the route the next morning as it is near the motorway and busy roads. The reception has a direct line to a taxi service and has a steak house on-site, plus it’s near some shops for supplies and coffee the next morning.
Day 4: Aylesford to Lenham (27.6km)
I got a taxi back to Aylesford before dawn and set off across the fields.
Shortly after passing through an underpass, you pass the White Horse Stone, the remains of a Neolithic long barrow and part of the Medway Megaliths.
The sun was bright as I entered Boxley and explored the beautiful churchyard.
I love gravestones and there were some beautiful ones here.
Walking out of Boxley, the terrain is gently rolling, well marked, and easy to navigate.
You will find lots of stiles on the route. Definitely be careful when it’s wet as they can be slippery.
Kent is famous for its oast houses which have a distinctive conical roof, some with little white caps. Originally, they were designed for drying hops as part of the brewing process, but most in the area have been converted into homes.
The path continues as an easy walking track.
Towards Lenham, you might spot a sleeping lifesized (wooden) pilgrim on a bench with the text, “Pilgrim bound with staff and faith, rest thy bones.”
I stayed at the Dog & Bear at Lenham which was the best accommodation of my journey. Really lovely room with a Nespresso coffee machine, which is basically what I need in the morning! It also had a heated towel rail, so I was able to dry my socks after washing them the previous day. This felt like luxury!
Day 5: Lenham to Boughton Lees (21.4km)
Much of the day is on country paths and walking through fields on the North Downs Way.
Lovely paths alongside fields. You can definitely walk this route in walking shoes if it’s not wet as the paths are so good, but I’d wear boots if it’s wet as it can get muddy.
Walking through the fields of Kent.
The B&B I had booked in Boughton Lees had just been sold, so I had to find a new place for the night. There are always challenges en route, even if you have booked accommodation!
I stayed at the Champneys Spa in the village which was in beautiful grounds, but I wasn’t able to take advantage of the spa because of the pandemic. It was a much more expensive option, but I didn’t want to walk on further that day.
Day 6: Boughton Lees to Canterbury (31.1km)
I left the hotel in the dark and the pouring rain and wind. Since the weather had been fine up to this point, it was good to test out my wet weather gear. I was grateful for my waterproof socks and the layers of dry bags I had for my gear as it rained pretty much all day.
I was very grateful for The Woolpack pub in the pretty village of Chilham where I stopped for a sausage sandwich and coffee by their open fire. I warmed up and dried off and then headed back out into the rain for the last push on to Canterbury.
Kent is famous for its apples and there were many varied orchards on the way. Some small and local and some huge farms.
I arrived in Canterbury (wind-swept) just in time for Sung Evensong in the Cathedral.
It’s well worth staying at The Canterbury Cathedral Lodge so you have access to the precinct after dark. There are police on the gate who will let you in if you go out to eat.
I stayed for two nights and spent the next day exploring the Cathedral as a tourist. See all my pictures of Canterbury Cathedral here.
This sounds like a fabulous walk with loads to see. Somehow, with both an A level and an English Literature degree, I’ve managed to swerve reading any Chaucer. Maybe I should bite the bullet in 2021 and then make the pilgrimage!
Thanks for sharing your trip.
Jo Frances Penn
There’s definitely no need to read Chaucer to enjoy the walk. I did it for Becket, not Chaucer anyway!
Great photos Jo. Really bring it to life. I’ve done sections over the years with the Ramblers. Maybe time to do the whole thing? I don’t think I could do quite such long sections each day though
Jo Frances Penn
Hi Andy, You could definitely take it slower. There are plenty of accommodation options on the route, so you could space it as you like. Glad you liked the pics.
The Archbishop, I presume? Not Samuel. In any case, I very much enjoyed following your walk, and had no idea it was that far or that it would take five days. Thanks too for the lodging and food ideas.
It must have been a fabulous experience all told. Quite an accomplishment!
Thanks for giving us a virtual walk in a time when we can’t travel so easily.
Jo Frances Penn
Glad you enjoyed it!
It’s been A busy day. Felt like I couldn’t get to what I wanted to do because work things and home life things all got in the way. Took a quick break got in my car and drove while listening to your pilgrimage episode. I was completely mesmerized—feeling like I was along with you. Your storytelling is amazing. As you concluded, I unexpectedly started crying. I felt relief for you, but also release for me. I’ve been so wound up trying to knock things off of my to do list, for a few moments I was able to journey along the pilgrimage with you. It’s definitely on my list. I saw a lot of myself in you. Thank you for sharing.
Jo Frances Penn
Thank you so much, Amber. Your words mean a lot to me. That trip means even more to me now as it was a last gasp of freedom before this shut-in winter misery. I’m so glad it gave you some release from pent up everything!
Jo Thanks for sharing your walk very interesting. Clearly I am not quite as adventurous. The intention is to walk it with a friend who wants to miss out and start of Rochester. The plan is I will arrive inLondon early morning. Visit the Tabbard site, have breakfast at the historical neighbouring p.h The George the authentic 17th century inn, visit Southwark cathedral then get the river boat to Greenwich and any other relevant points en route and arriving in Rochester late on the same day to meet up with my friend and both start walking to Canterbury from there.
I am trying to work out what other relevant spots I should journey too relevant to Chaucer’s journey before arriving in Rochester. If you have any ideas would appreciate to receive them.
Thanks in anticipation and all the best
arriving in Rochester to c
Jo Frances Penn
Rochester is a good starting point, for sure. I would skip breakfast at The George and have it at Borough Market, one of the foodie destinations of the UK and right next to Southwark Cathedral. Chaucer would have approved!
Thank you for this enjoyable and informative account. It has inspired me to do this walk soon.
Jo Frances Penn
Thanks, Kathy, I’m so glad you enjoyed it!
Hi, what make of walking shoes did you wear for this trek? There is a fair bit of road so one needs a pair that is comfortable for walking on both concrete and country paths. I’ve done a lot of walking in London recently which can be quite punishing as almost all of the routes are on hard surfaces, even in parks, and I got a fair few blisters. I’m really keen to do this route but in installments rather than in one long stretch.
Jo Frances Penn
I wear Meindl Respond Lady GTX walking shoes. I love them! I only got one tiny blister on this walk.
I note a compass comes in handy for this walk. I’ve only done eight miles of it so far (Otford to Trottiscliffe) but I find it quite clearly signposted with plenty of signs pointing to the North Downs Way where the route changes from road to footpath. Are there sections later on when it becomes ambiguous and the traditional Pilgrims’ Way diverges from the North Downs Way?
Jo Frances Penn
Hi Simon, I only really got a bit lost in the London section, so the pilgrim’s way before Otford. The rest is signposted as far as I remember. I took a compass but didn’t use it. I did use Google Maps occasionally though!
Hello, I’m currently do this walk and have really enjoyed your blog. Did you leave any of the route out from Otford to Aylesford. As the Cicerone guide directs the walk up to hailing- then back down again. Did you go up and down- or take a more direct route across country? Would I be missing out ( and cheating haha) if I did?
Jo Frances Penn
I followed the route in the guide book and it was a beautiful day! Have a good time.
This is a wonderful travel report; much appreciated. A friend asked me earlier today if I’d be interested in walking from either Winchester or London to Canterbury. I jumped at the unexpected opportunity for another long-distance walk in England! It was good to find your blog when I started looking around online. My friend wants to take a group of young people on the pilgrimage; starting in the heart of one of the world’s leading cities might be perfect for teenagers. Lots to think about; thank you for a great introduction!
Jo Frances Penn
I definitely enjoyed this walk — and I can also recommend the St Cuthbert’s Way which has more nature and out of way walking.
Jo Frances Matthews
Morning! Loved reading this. Very inspiring!
I am also Jo Frances so considered this a positive omen. I live in Kent and know a lot of the places but this would be the first pilgrimage, and will lead, eventually to the Sultan’s Trail…hopefully 🙏
Jo Frances Penn
Enjoy the walk 🙂
Is it possible to do it in 3 days you think? What about 4? Do you k ow what is the easiest way to get back to London?
Jo Frances Penn
Only you can decide how far to walk each day. It’s 180km, so 3 days would be 60km per day — I don’t know how that would be possible for most people! 4 days would be 45km per day, and that would be too much for me. You could just do a section e.g. the last few days to Canterbury.
You can get a train back to London from Canterbury, not a problem!