Canterbury Pilgrimage AAR: 2-Week Hike from Winchester to Canterbury (England)
When my friend Kelly first mentioned hiking the Canterbury Pilgrimage, I'll admit I was skeptical. I'd never done a long-distance hike before, and two weeks walking across England seemed ambitious at best. But Teresa and I said yes anyway, and that decision led to one of the most memorable adventures of my life.
When my friend Kelly first mentioned hiking the Canterbury Pilgrimage, I'll admit I was skeptical. I'd never done a long-distance hike before, and two weeks walking across England seemed ambitious at best. But Teresa and I said yes anyway, and that decision led to one of the most memorable adventures of my life.
The Canterbury Pilgrimage follows the historic Pilgrims Way from Winchester to Canterbury, the same route immortalized in Chaucer's Canterbury Tales. Over two weeks in June of 2023, we hiked through some of the most beautiful countryside England has to offer, stayed in quaint villages, explored ancient churches, and learned valuable lessons about packing light, staying hydrated, and stopping to smell the flowers.
This is our complete guide to the Canterbury Pilgrimage, including planning, packing, daily experiences, gear that worked (and didn't), and practical lessons for anyone considering this trek.
Teresa on the Pilgrims Way or AKA The Canterbury Pilgrimage in southern England
Planning Our Canterbury Pilgrimage: How It Started
When I first heard about this I was intrigued to say the least. I had never really considered doing a pilgrimage before or even doing extended length hiking trips of any kind. Enter Kelly, a lifelong friend and adventurer(she married one of my best friends in high school and was in our Dungeons and Dragons group). She tells of this adventure in England where she was planning to hike from town to town and follow the original Pilgrims Way laid out in the Canterbury Tales as well as a few notable stops while in London as well. (We also saw The Phantom of the Opera while in London!)
Well, us being the adventurous types that we are, we asked if there was room in the group for us too! As it turned out, the three of us would be the WHOLE group which actually worked out really well. So we started planning the adventure of a lifetime.
Our friend Kelly working her way through a "kissing gate" amid a veritable sea of Stinging Nettle!
Packing Light: The Backpack-Only Strategy
We decided early on to only bring what we could carry in our backpacks. Gone would be the "checked bag" at the airport as well as bringing computers and the associated baggage required for their operations. This actually made the airport part of the journey very easy as we didn't have to stand in lines for the check bag counter nor did we have to deal with baggage claim at all. It was very liberating to be honest.
The first thing we decided to do was limit our equipment to what we could carry in our respective backpacks. This eliminated a literal mountain of gear that we had deemed needed but optional. It also made the journey much nicer. We finally decided on a couple of changes of clothes, I took a small amount of camera gear in a dry bag (since it rains in the UK a lot), and a water bottle. We would pick up snacks along the way and add that to our loadout as we needed it.
Lightweight travel concept of only taking what fits in a backpack and nothing more is very liberating.
This also generated another benefit with our travel: the airport processing got A LOT simpler this way. We literally didn't check anything, so we just went through the TSA checkpoint and carried our packs right to the gate. Our hands were free to do things like buy coffee or get out credit cards! It made traveling so much less stressful to be quite honest that I might be adjusting my future travel to operate in this mode. You never lose your luggage as you walk onto the plane with it and it fits into the overhead space without issue... every time. This was glorious for me as I worry about the luggage making it to the same place as me or even worse, not arriving at all.
Just consider this a travel hack that actually works if you can live without all the stuff in your check bag…
Camera Gear for 2 Weeks of Travel Photography
Since we had decided to travel so light, I took a hard look at the camera kit I would use on the trip as well. I whittled it down to just the Leica CL, the TTartisan 17mm f1.4 L mount lens and the 35mm f0.95 L mount lens. That's it, no other gear whatsoever. Well... there were batteries and a charger, but you get the point here. So I quickly learned that I liked the 17mm in London and then once we got to Winchester I switched to the 35mm and left it in place almost the rest of the trip. To be honest, I could have left he 17mm at home and it would have been fine…lesson learned.
The author with the Leica CL mirrorless camera and the TTArtisan 35mm f0.95 lens on the Pilgrim's Way
For this trip I decided to travel light so I took my Leica CL and two prime lenses: the 17mm f1.4 and the 35mm f0.95 prime lens. Turned out I wished I had taken the 35mm f1.4 as it is smaller and lighter than the 0.95 aperture lens and would have saved me some weight. I don't know if I even once opened up to f0.95 on this trip, even at night. I just didn't need it, so it was wasteful to bring it.
I took a dry bag to protect the camera gear since it rains in the UK a lot. Smart decision, as we did hit some wet weather!
Mystery Ranch Backpack Review: 25-30 Pounds, No Back Pain
As for hiking gear, my loadout for this trip was as follows: I had a full change of clothes plus extra socks, I also took my phone charging gear, a Katadyn water filter as I was not sure if I would have ready access to clean water. Sometimes you don't have that access to be honest, and I wished I had taken another water bottle as well... I took a single Nalgene quart water bottle, a ziplock bag of snacks from the grocery store, a rain coat, and my dry bag with my camera gear in it, and that’s it.
I picked up a set of trekking poles in Winchester that I almost wore out by the end of the trip. My backpack that I used on this trip is a Mystery Ranch Pitch 40, which is actually geared toward rock climbing but worked just fine for this trip. I am going to take a moment here to point out that a really well-engineered backpack makes all the difference in the world. I was carrying about 25 to 30 pounds from day to day and my back was NEVER sore or painful from the pack, not even once. I can absolutely, and with certainty recommend Mystery Ranch backpacks after this trip. They work.
I never really understood how to properly use a backpack, but after using this one, I figured it out and got it dialed in. It is not really designed for this kind of trek, but rather it is engineered for route climbing and carrying rope and chalk and harnesses and such instead. I just used it anyway as it is what I had at the time. This didn’t seem to be a problem though as the load bearing system puts the load on your waist and not your shoulders. This is where people get things wrong because small bags and haversacks place the load on the shoulders and this causes fatigue unnecessarily. If you adjust your pack properly, you can carry it for hours and you will just be tired from the trekking and you will be sweaty from the physical workout, but your back will not hurt.
Arriving in London: Tourist Mode Before the Trek
Big Ben in London England is an incredible iconic landmark that is a must see if you are in London. We did the usual tour and then went for a walk, which is how I was able to get this photo with the Leica CL and the TTArtisan 35mm f0.95 lens.
Once in England we started in London where we did the usual tourist stuff for a couple of days ahead of starting the pilgrimage proper. This included a bus tour and a short trip to the British Museum as well. We even took in the Phantom of the Opera while in town. What a treat that was! I was wholly unprepared for the experience that is the Phantom of the Opera, totally worth it.
The daughter went with us to visit London and to hand out with us for the first few days of the Canterbury Pilgrimage, even though she cheated…
Well, once on the ground in England we checked into our hotel and went for some food. What we found is that the food in the UK is... different... from what we are accustomed to here in the US. We had to adjust to this as it seemed that they have a very specific diet and do not vary from it for any reason. We joked about how for a country that conquered most of planet earth at one point for spices…. doesn’t know how to use them! I will never understand this whole “beans on (soggy) toast” thing either…
We spent the next couple of days being tourists in London for the sake of brevity, then we embarked on the mission to Winchester to start the pilgrimage. We saw all the usual stuff, like Piccadilly Circus and Trafalgar Square and Westminster Abby and such, but it was only for a day or so, then it was off to Winchester!
The fence outside the British Museum showcasing the iconic telephone booths in London.
Winchester Cathedral: The Official Start
Interior of Winchester Cathedral in Winchester England.
Once in Winchester we attended a service at Winchester cathedral and received a blessing from the priest before we started, which was a really nice touch to add to the whole experience to be honest. If you do this hike, I recommend attending a service at the cathedral even if you're not really religious and hear the boys choir. The singing is beautiful. It also just adds a little something special to the trip in my opinion. I think the evening service is called “Evensong” or something like that, it is beautiful. We also found an outfitter in town (who would have guessed that there would be a HIKING outfitter at one end of the Canterbury Pilgrimage? HaHa) and this is where we learned about the value of trekking poles and decided to get a couple of sets for me and Teresa. I am really glad we did too, they helped so much! I will not do long hikes without them anymore. Once you see how much they help with load distribution as well as balance, you will never want to hike without them again too.
Now the adventure officially begins…
Winchester to Arlesford (First Steps)
Well, we strike out and head for the next town and I must say at this point that the English countryside is absolutely gorgeous! We couldn't get over how everywhere we looked that it looked like a postcard! We walked by beautiful fields, streams and all these little communities with some of the nicest people we have ever met!
The first “destination” was Alresford which is a quaint little village in the countryside that has several really old buildings (which becomes a recurring theme on this trip). One of which was constructed before the USA even existed. I point in out in one of the videos listed below actually. It turns out that it takes a lot longer to cover 8 to 10 miles than I thought it would too, we were complete neophytes at this and were REALLY over ambitious about how fast we would move on the trail, turns out we go ALOT slower than we thought… this resurfaces later in the blog, but just keep that in mind if you think you want to do this hike.
Wheat field south of London England on the Pilgrim’s Way of the Canterbury Pilgrimage.
Some of the things we have learned are that stinging nettle is a legit plant you don't mess with and it is literally EVERYWHERE. Another one is that the locals are very friendly, especially the older ones, and are a real treat to chat with when you find them here and there. They loved my accent most of the time and would call me “the Yank” when they would hear me talk…it was almost comical as I have a very strong Appalachian accent as you can hear in the video as well. The trail also isn't just a hiking trail through the woods, but more of a "way" which will cross fields, go down designated paths or even along roads at times. You really have to pay attention to make sure you don't miss your turn...ask me how I know.
All that aside we had a wonderful first day on the trail, albeit a long one where we ran into really interesting people and also learned a few things about the local flora and fauna we didn't know either.
English Countryside: Why It Looks Like Postcards
The English countryside is some of the most picturesque terrain I have ever laid my eyes on, and for the locals it is just...home... I have seen a lot of beautiful places on this earth and they all have a charm. The charm here is the people and how they groom the landscape for agriculture beautifully. It is literally a postcard in almost any direction you look. So I did just that, took photos in every direction, and wound up with something like 1400 unique images when I got home two weeks later.
When you would cross from one field to another or maybe pass from the forest to the fields, you would come to one of these gates in a variety of forms, all of them would work in a pretty similar fashion, but nonetheless, it would be there. This is a simple cattle gate but in the United Kingdom, it is called a kissing gate for some reason. Above you can see Kelly passing through a modern steel kissing gate and they are all over these trail systems in England.
So first things first, hiking this trail is actually really fun. It could be monotonous for someone who isn't comfortable with their own thoughts for hours at a time, but it was fine to me. I didn't even listen to music on this trip, I was just...there...
Day 2: Arlesford to Alton (The 13-Mile Mistake)
From Post 2: This is the hotel we stayed in and it was simply adorable. The whole first floor of the part you see here is a restaurant/pub and the hotel is L shaped with a significant portion out back behind this street facing portion. The rest of the town is also really neat to me as well.
Swan Hotel Alresford England is a beautiful and very old hotel on the Pilgrim’s Way trail.
So the next morning we leave out for the next town and make pretty good time. Alton is a larger town and we are hoping to be there by lunch. Well, turns out the girls decided to take public transportation after about 5 miles or so and I decided to leg it on in... this would prove to be painful.
Hardware store in Alresford England is typical of the types of buildings you will find on the Pilgrim's Way.
I had looked at the map and speculated it to be about 10 miles to Alton and figured I would probably cover the remaining 5 miles in about 3 hours since I would be stopping to get photos and the erratic nature of the trail layout and such as that. Well, this turned into a 6-hour slog that added up to an additional 13 miles for the day! It even got to the point where I realized I needed to cover ground more rapidly or I would miss supper so I stopped capturing video for the YouTube channel all together and just grabbed the occasional photo instead. You read that right, 18 total miles in a single day, for a beginner trekker who had done almost no train up for this trip. What I had also forgot to account for was the fact that a lot of it was in the direct sun an really hot. I ran out of water probably with 2 hours left to hike if memory serves me and there was no where to stop and get more without trespassing on farmland. This is important as the trail passes through all this beautiful countryside and we are given special permission to use these trails, but we can not deviate from the trails, you have to stay on the trail. So if the trail doesn’t cross a stream, then there is no water. On this day, it didn’t even pass by houses hardly at all, it was just one field to the next, over and over, with occasional diversions down the country roads (that didn’t have shoulders at all in places).
Hydration on a hike is critical and also taking in electrolytes too. I lost a lot of electrolytes on the Pilgrim’s Way trail to Canterbury as this shirt can attest!
Now to be fair, I did cross a lot of beautiful countryside on this leg of the trip and I don't regret making the trek this day, but I failed to drink enough water and had debilitating cramps later that night from dehydration. The lesson here is to drink more water, especially if you are doing an activity that is physically demanding in any way.
I grabbed this photo about midway through my 18 mile day with a single quart of water…lesson learned.
Over the course of the next two weeks we would explore numerous old churches as well as eat in many of the most quaint pubs you have ever seen! The bulk of the trek though is through the country with some parts being out in farmland for hours at a time on trail. You really need to make sure you take enough water when you leave too, as there are times when water just isn't available. I ran out on the 18 mile day and had debilitating leg cramps later that night because of dehydration. It is a thing y'all, don't scoff at this part: drink electrolytes and water, it matters…
Infrastructure and Details: What Makes England Special
Here we have the road crossing (well, more like a tunnel under the road actually)heading into Alton where you walk under the road to get into the town proper. This is the kind of thing you don't see much where I live and I found interesting. The footpaths are so important to the English that they build this kind of infrastructure to keep them operational. I wished we would have done this with the old hiking trails from our country's early settlements and made them into hiking trails today...just a thought.
Trail tunnel under a main highway for the Pilgrim's Way heading into Alton England
Here is a perfect example of what I am talking about. This bridge is pre-war era construction. The reason I know this is because the whole thing is riveted together. Any other modern form of metal joining would be significantly cheaper than rivets. Arc welding wasn't really common place till after World War 2 so rivets were used everywhere till then. If I had been a typical traveler heading to the next destination, I most likely would not have noticed this.
Pre-war riveted foot bridge to a train station in southern England.
Mid-Journey: Farnham and the Stepping Stones
The next day we really didn't do much hiking as I escorted Sierra to the airport and then went back and linked up with Teresa and we made our way by train over to Farnham. We really wanted to explore the town and Kelly had already went ahead on her own so it was the perfect opportunity. We had a great time in Farnham and found Kelly later so it all went great.
Then the next day we leave Farnham and make our way over to the stepping stones which is a huge deal on this trail and I didn't even know about it till this morning. These stepping stones are part of the trail system and when we found them we decided to make a small event of it and enjoy a few minutes at this location to make it a little more memorable. If you would like to see the stepping stones just watch the video linked above. I didn't get my camera out of the dry bag here for obvious reasons so I only have video from this location.
These kinds of treks are not just about seeing how fast you can cover ground or seeing how many miles you can hike in one day, but about stopping and smelling the flowers or grabbing some photos. This is what this pilgrimage was about for me.
One of the many old churches in southern England on the Pilgrim's way (Canterbury Pilgrimage)
The Pilgrimage Experience: Disconnecting and Reflecting
This hike was a twofold event. First it was a way to explore England in a more intimate way than seeing the usual tourist sites and then hopping on a plane for the states. This way we get to talk to the locals and see parts of the country that other visitors will never see, eat food that they will never taste, and just enjoy the country like a traveler should.
The second part or probably what should be considered the first part is the pilgrimage part of the trip. A pilgrimage is a trek to a significant location for the purpose of reflection and to be able to spend time with the Lord. I had ample time for this too. You get to be with your own thoughts a lot if you keep your cell phone put away, which I did, this will give you a lot of time to reflect. I am glad I did this as it allowed me to just disconnect from life for a while and to be able to just enjoy where I was at the time without having to think about what I was going to do the next day or whatever.
This was so important to me that I didn't even post much about the trip while on it. I used the map function most of the time (there is a website where you can get the route and it overlays on Google maps). This was wonderful for someone who has grown VERY accustomed to using their phone a lot.
Above is one of the many churches we explored on our pilgrimage to Canterbury. Over the course of the next two weeks we would explore numerous old churches as well as eat in many of the most quaint pubs you have ever seen!
The Pilgrim's Way to Canterbury England is a beautiful hike. A quality backpack will make all the difference too.
Canterbury and completing the pilgrimage
After about two weeks we finally walked out of a field, into an old road and there it was…Canterbury! We had finally made it and the sense of completion is hard to describe. The long days on the trail, the injuries, the dehydration cramps, all those photos to sort through… It was surreal to be honest about it. We stopped at a pub to get a bite to eat and had a wonderful time chatting with the locals before heading into the old city to check into our hotel. The Cathedral Gate Inn (I think that is the name) is ANCIENT!!!! There were all sorts of oddities associated with this Inn, but aside from that we have made it to the Cathedral! We went to the ticket office to go into the Cathedral grounds and when the attendant figured out we were Pilgrim’s he personally escorted us FREE OF CHARGE (at this point I don’t know if there is a charge, but he got real excited when he figured out we were pilgrims) to the courtyard to the marker that signifies the official end to the hike.
Trail End Stone at Canterbury Cathedral in Canterbury England
We all made our photo with the stone and then went for supper. Later we were treated to a special blessing from the priest at Canterbury Cathedral as well as being personally escorted to the Pilgrim’s Sanctum in the far back of the church. The story is that all the stained glass in the other churches are of Christ, the Saints and biblical events BUT here all the stained glass is of PILGRIMS to honor those who make the journey and we were the latest ones to get there. This was after Evensong service with the boys quire and the pipe organ. If you have never heard this and you have the chance, you really should experience it for yourself. It was incredible.
Canterbury Cathedral is so large and ornate that it is impossible to capture it in one photo. I opted to just get this one spire as some of it was obscured by scaffolding and the rest was just so large. This photo shows the level of detail and the sheer scale in just one photo. It is hard to imaging a Cathedral can be so large. Canterbury has to hold some sort of record for this…
What I Learned: Practical Lessons for Future Pilgrims
Let's talk about what really matters. In closing, I am going to wrap this with the following quote that I made up just for this blog, but it does seem fitting to me: "If you don't stop to look at the flowers along the way, you wasted part of your trip."
I am really one of those people that likes the journey as much as the destination and this was the perfect blend for me. Daily goal-oriented activity with lots to do and see along the way...
Key lessons:
Drink more water than you think you need (I learned this the hard way with debilitating leg cramps!)
Pack lighter than you think (I should have taken the 35mm f/1.4 instead of the heavier f/0.95)
Stop to smell the flowers (literally and figuratively)
The journey IS the destination (don't rush through beautiful countryside)
Backpack-only travel is liberating (no checked bags, less stress!)
A good backpack matters (Mystery Ranch saved my back)
Support this website by using these affiliate links to shop on Amazon:
Nikon AF-S FX NIKKOR 105mm f/1.4E ED Lens
Voigtlander Nokton 35mm f/1.4 II
Sandisk 128GB Extreme Pro memory cards
Nikon 50mm f1.8 S Lens for Z mount
Canterbury Pilgrimage FAQ: Planning Your Own Trek
How long does the Canterbury Pilgrimage take?
The complete Canterbury Pilgrimage from Winchester to Canterbury is about 120-130 miles depending on your exact route. Most people take 10-14 days to complete it, averaging 10-15 miles per day. We took two weeks and found that pace comfortable for stopping to explore villages, photographing the countryside, and actually enjoying the journey rather than just grinding out miles. If you're a strong hiker you could do it faster, but I'd recommend taking your time! The whole point of a pilgrimage is reflection and experiencing the journey, not setting speed records.
What's the best time of year to hike the Canterbury Pilgrimage?
Late spring through early fall (May through September) is ideal for the Canterbury Pilgrimage. The weather is milder, days are longer, and most of the pubs and accommodations are fully operational. We went in [season] and had great weather overall. That said, England is England, so expect rain regardless of when you go! I carried my camera gear in a dry bag the entire trip and I'm glad I did. Winter is possible but you'll face shorter days, colder weather, and some accommodations might be closed.
Do I need to be religious to do the Canterbury Pilgrimage?
Absolutely not! While the Canterbury Pilgrimage has deep religious roots (it's been walked by pilgrims for centuries), plenty of people hike it for the history, the beautiful countryside, or just the challenge of a long-distance trek. I approached it as both a spiritual journey and an adventure, but you can focus on whichever aspect appeals to you. That said, I do recommend attending the service at Winchester Cathedral before you start, even if you're not religious. The boys choir is beautiful and it adds something special to the experience!
How much does the Canterbury Pilgrimage cost?
Budget varies widely depending on your accommodation choices and eating habits. We stayed in hotels and B&Bs and ate at pubs every meal (since we didn't pack cooking gear), which probably ran $100-150 per person per day including accommodation and food. If you camp or stay in hostels and cook your own meals, you could do it much cheaper. The trail itself is free to walk. Don't forget to budget for getting to Winchester and from Canterbury back to London. Flight from US to London obviously adds to the cost, but we saved money by only carrying backpacks (no checked bag fees!).
What should I pack for the Canterbury Pilgrimage?
Pack lighter than you think you need! We went backpack-only (no checked bags) and it was liberating. My essentials: full change of clothes, extra socks, rain jacket, water bottle (I wished I'd brought two!), water filter, trekking poles (bought in Winchester), phone charging gear, camera gear in a dry bag, and snacks. I carried 25-30 pounds in a Mystery Ranch Pitch 40 backpack and my back never hurt. The key is a well-engineered backpack with proper weight distribution. Pack for the reality that you'll be carrying everything on your back for two weeks, not for every possible scenario!
Where do you stay on the Canterbury Pilgrimage?
You have options! We stayed in hotels and B&Bs in the towns along the route (Arlesford, Alton, Farnham, etc.). The advantage is comfort, hot showers, and you can just show up without reservations in most cases. The disadvantage is cost. Other options include camping (England has lots of campsites), hostels, or even churches that offer pilgrim accommodation. Some people book everything in advance, others wing it day by day. We were somewhere in between and it worked fine. The towns are spaced reasonably for daily hiking distances.
How hard is the Canterbury Pilgrimage physically?
If you're in reasonable shape and can walk 10-15 miles a day, you can do this! I'd never done long-distance hiking before and I completed it fine. The trail is well-marked and not technically difficult (no rock scrambling or anything like that), but it's still physically demanding to walk day after day. The biggest challenge for me was my 13-mile mistake day where I hiked farther than planned and didn't drink enough water. I had debilitating leg cramps that night from dehydration. Learn from my mistake: drink more water than you think you need, especially on long days!
What's the trail like? Is it easy to navigate?
The Pilgrims Way isn't a single continuous trail through the woods. It's more of a "way" that crosses fields, follows designated footpaths, and sometimes goes along roads. You'll encounter lots of kissing gates (cattle gates) when crossing between fields. The trail is generally well-marked but you do need to pay attention to avoid missing turns. We used a website that overlays the route on Google Maps which was incredibly helpful. The countryside is absolutely gorgeous, literally like postcards in every direction!
Do I need special hiking gear or can I use regular stuff?
You don't need ultra-technical gear! I used a rock-climbing backpack (Mystery Ranch Pitch 40) and it worked great. Trekking poles are highly recommended (I bought mine in Winchester and almost wore them out). Good hiking boots or trail shoes are important for two weeks of daily walking. Rain gear is essential. A water filter is nice to have but not strictly necessary. Camera gear is optional but highly recommended—the English countryside is stunning! I took my Leica CL with two lenses and got 1,400 photos. Looking back, I wish I'd packed my 35mm f/1.4 instead of the heavier f/0.95 lens.
What's the deal with stinging nettle?
Stinging nettle is a plant that's literally EVERYWHERE along English trails and you do NOT want to mess with it! It causes a stinging, burning sensation if you brush against it. The locals just accept it as part of life, but as an American, it was something I had to learn about quickly. Wear long pants when hiking through overgrown sections, and don't grab random plants for support. The stinging sensation is temporary but annoying. This was one of our first lessons on Day 1 and we got much better at avoiding it after that initial encounter!
Until next time, get your camera out and go take a picture with it.