Overview
A six day, self-guided walking holiday, following a carefully-crafted itinerary between Rochester and Canterbury in Kent, each boasting important cathedrals. This route not only links these ancient, sacred cities but also intertwines both the traditional Pilgrims’ Way and the North Downs Way. Both of which are, for the most part, a designated Area of Outstanding Natural Beauty.
Walk along ancient byways and through forests, orchards and vineyards, and up onto rolling chalk downs, with each day leading you to an old English village, where traditional inns are still very much at their heart. Don’t miss getting a Pilgrims’ Passport in Rochester, and have it stamped at the many historic churches along the way. This walking holiday is easily accessible by train from London, and a superb addition to a city break.
- Rochester Cathedral
- Rochester Castle
- Canterbury Cathedral
- North Downs Way
- Pilgrims’ Way
- Kent Downs – an Area of Outstanding Natural Beauty
Itinerary
Day 1: Arrival Rochester
Arrive in Rochester, an ancient town with both an impressive castle and cathedral, and an important stop on the ancient Pilgrims’ Way, which originally started in London. Take time to visit the cathedral, which is the oldest in England, and where you can buy your Pilgrims’ Passport and have it stamped. It’s also worth exploring the historic centre and newer river district, on the River Medway. You will see many references to Charles Dickens too, as he spent his formative years here, with locations inspiring the likes of Great Expectations and The Pickwick Papers.
- Accommodation: Travelodge or similar in Rochester
Day 2: Rochester to Thurnham | 20.9km
Walk straight from Rochester along the River Medway, as ancient and more modern urban developments quickly change to natural environments, with the likes of Baty’s Marsh and Nashenden Nature Reserve leading up eventually to the North Downs Area of Outstanding Natural Beauty. You know you have left the town behind when you ascend onto Wouldhham Common and surrounding wheat fields, with views across the River Medway to Rochester in the distance. The walk continues along a combination of ancient Pilgrims’ Way paths and soothing North Downs, with many historic highlights along the way, including Kit’s Coty Neolithic burial chamber. Don’t miss the hole in the hedge in Detling that leads up to the day’s finale, following a narrow chalk path with magnificent views all the way to Thurnham.
- Walking for the day: 20.9km
- Accommodation: The Black Horse Inn or similar in Thurnham
Day 3: Thurnham to Lenham | 14.1km/16km
Walk directly from the hotel to the ruins of Thurnham Castle, with the trail soon opening up into meadows, following chalk paths up onto ridges and through ancient forest, all with great views over the North Downs area. The Dirty Habit pub in Hollingbourne is a lovely stop for coffee or lunch if you started later, and from here you continue along many sections of the North Downs Way, a gentle route that takes you to the market village of either Lenham of Charing, depending on accommodation. Don’t miss a quick diversion to see the wooden sculpture of a shepherd at the Woodland Trust’s Hucking Estate along the way, which is also a stunning viewpoint. As well as Lenham Cross carved into the hillside on the approach to Lenham.
- Walking for the day: 14.1km (16km, if accommodated in Charing)
- Accommodation: Dog & Bear Hotel similar in Lenham
Day 4: Lenham to Chilham | 24.6km
This is a long but luscious day, taking you back onto the Pilgrims’ Way, past Lenham Cross again, and then along straight paths through bird-filled woodland into open fields that stretch for miles. This long, meditative stretch on the Pilgrims’ Way then leads to Eastwell, overlooked by a grand manor house, now a hotel, where the nearby ruined Eastwell church hidden behind trees is not to be missed. From Boughton Lees, continue up to Kings Wood, a vast stretch of stunning mixed conifer and broadleaf woodland, with your first view across to Canterbury Cathedral before it dips down to Chilham. It is said that, in ancient times, pilgrims traditionally gathered in the woods to avoid robbers. Today it is forest bathing heaven, especially in bluebell season. The walk today can be shortened using a taxi transfer to Boughton Lees (payable locally).
- Walking for the day: 24.6km (shorter option – 9.6km)
- Accommodation:The Woolpack Inn or similar in Chilham
Day 5: Chilham to Canterbury | 11.7km
Today’s walk to Canterbury is a shorter one, but one that takes you through some of Kent’s finest orchards, ancient woodland and all round pastoral perfection. This shorter day means that you arrive in England’s most celebrated cathedral city in good time to visit the sacred site itself. Not only is Canterbury Cathedral the seat of the Archbishop of Canterbury, it’s also the notorious for being the place where, in 1170, Archbishop Thomas Becket was murdered inside the cathedral by four knights loyal to King Henry II. Our first accommodation choice is the Lodge inside Canterbury Cathedral, which is a sanctuary in the city, but it does book up quickly, so we have other accommodation options too.
- Walking for the day: 11.7km
- Accommodation: Canterbury Cathedral Lodge or similar in Canterbury
Day 6: Departure
Departure after breakfast.
What to expect
Accommodation
Accommodation on this tour includes a mix of mostly small, locally-owned hotels, B&Bs and traditional inns. They have been carefully selected based on a variety of criteria including their proximity to the Pilgrims’ Way, warm hospitality, fine local food or commitment to responsible tourism. All rooms have en-suite or private bathrooms.
Click to view our default hotels for this trip
- Travelodge (Rochester)
- The Black Horse Inn (Thurnham)
- Dog & Bear Hotel (Lenham)
- The Woolpack Inn (Chilham)
- Canterbury Cathedral Lodge (Canterbury)
Accommodation is subject to availability. In the event of a particular hotel or guesthouse being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Meals
Accommodation is on a bed and breakfast basis. In some locations, picnic lunches can be ordered on request at the hotels, but otherwise there is no shortage of shops in the towns or villages where you stay, or pubs and cafes en route. You can have dinner at your hotel or at nearby restaurants.
Difficulty and terrain
This tour is graded moderate with daily distances ranging from 11-25km (read more about difficulty grades). The walks follow a mix of byways, forest paths and footpaths.
We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime.
When to go
This trip is available from March to October. The flexibility of self-guided holidays means that there are no fixed dates, and you can start your trip on any date during the season. For more information, see our blog, Best time to visit England.
Getting there
Up-to-date travel advice on the United Kingdom is available here (for Canadian citizens) and here (for US citizens).
Click to view travel options and route planner
By plane
London Airports are the most convenient for reaching the start point of Rochester.
By train or bus
- If you are able to travel to England without flying, this holiday is reachable by rail with train stations in Rochester and Canterbury. Direct trains from London Victoria and London Bridge to Rochester train station take approx 45mins. Trains also run to Rochester from other locations.
- From Canterbury, trains can be taken for onwards travel to London (approx 1h journey) or other destinations.
- For more information, tickets and timetables, please visit ThamesLink and National Rail.
UK Visa and entry requirements:
IMPORTANT: From 2025, the UK is implementing a new Electronic Travel Authorisation (ETA) for many countries around the world. Up until 08 January, the ETA requirement only applied to nationals from Bahrain, Jordan, Kuwait, Oman, Qatar, Saudi Arabia and UAE.
On 08 January 2025, the ETA requirement was extended to visitors from eligible non-European countries, including Australian, Canadian and US nationals. Then, on 02 April 2025, the ETA requirement was extended to eligible European countries, referring to most of Europe.
You can view the full list of countries that this applies to here and apply for your ETA here, or on the UK ETA app. The ETA usually takes up to three working days to be processed, although we advise applying as early as possible, in advance of your travel dates. People travelling with an Irish passport don’t need an ETA.
You can read more about the UK entry requirements on our blog.
Inclusions
Included
- 5 nights accommodation
- 5 breakfasts
- Luggage transfers on all walking days (one piece per person, max 20kg)
- Access to your digital pre-departure information (accommodation list, GPS map of the route, baggage transfer information, itineraries, route information of cafes, restaurants, local bus timetables, etc.)
- 24/7 phone assistance by our local office/representative
Excluded
- Airfare and connecting land transfers
- Lunches, dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Personal expenses
- Any items not specifically mentioned as included in the programme
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- This holiday is available for solo travellers. However, a supplement will be charged as the cost of rooms and also luggage or private transfers (when applicable) is not shared. Please note that solo travellers are always accommodated in their own room. For logistical reasons, we don’t offer an option for solo travellers to share rooms with other solo travellers.
- Extra nights are available upon request
