Passing through the Kent Downs, an Area of Outstanding Natural Beauty, this 6-day self guided walking holiday coincides with some of the old Pilgrims’ Paths and takes in the places that Chaucer’s pilgrims visited in the Canterbury Tales. Your adventure starts in Rochester and takes you to England’s most prominent Cathedral City – Canterbury. Re-energise mentally, physically and spiritually, reconnect with our cultural heritage and the natural world while enjoying the company of other pilgrims and like-minded walkers you meet on the route.
- Canterbury Cathedral and Rochester Cathedral – places of worship for more than 1400 years
- Rochester Castle – built about 1127 by William of Corbeil, Archbishop of Canterbury, with the encouragement of Henry I
- The beautiful varied countryside of the Garden of England
- Chatham Dockyard, established in the mid-16th century
- Kent Downs – an Area of Outstanding Natural Beauty
Click to view map
Day 1: Arrival Chatham/Rochester
Your tour starts with a overnight in Rochester or nearby Chatham with its historic dockyard. The following morning you begin your walk from Rochester. This historic town has a magnificent cathedral (the second oldest in England) and a well-preserved Norman castle, as well as many associations with Charles Dickens. Undoubtedly, Chaucer’s pilgrims would have come through Rochester, close to which the North Downs Way passes today.
- Accommodation: Ship & Trades in Chatham or similar
Day 2: Rochester to Thurnham | 12 mi / 19 km
Start the day by crossing Wouldham Common, pass Kit’s Coty Neolithic burial chamber and the White Horse standing stone along paths and fields to Boxley Church. East of Kits Coty, a long stretch with distant views delivers the North Downs Way to Detling Hill, beyond which a sudden return to open country shows the vast expanse of the eastern Weald spread below. The trail tucks round the outline of Thurnham Castle, from where you leave the trail for the short walk to The Black Horse in Thurnham.
- Walking for the day: 12 mi / 19 km
- Accommodation: The Black Horse Inn in Thurnham or similar
Day 3: Thurnham to Lenham | 8 mi / 13 km
After breakfast, re-join the route at Thurnham Castle and walk on to Hollingbourne, from where you follow a gentle route for many miles to the market village of Lenham where you overnight or in the lovely medieval village of Charing.
- Walking for the day: 8 mi / 13 km (10 mi / 16 km, if accommodated in Charing)
- Accommodation: Dog & Bear in Lenham or similar
Day 4: Lenham to Chilham | 15 mi / 24 km
The route continues to Boughton Lees and then enters Kings Wood, where pilgrims traditionally gathered together in medieval times to try and avoid robbers. Glimpses of Canterbury Cathedral can be had in breaks in the trees. Our final night before Canterbury is spent in the lovely small village of Chilham. The walk today can be shortened using a taxi transfer to Boughton Lees (not included).
- Walking for the day: 15 mi / 24 km (shorter option – 6 mi / 9.6 km)
- Accommodation: Woolpack Inn in Chilham or similar
Day 5: Chilham to Canterbury | 7.2 mi / 11.5 km
Enjoy your hearty breakfast and set off on your final walk to Canterbury and hope to arrive in the city by lunchtime. There is time to spend in this beautiful city along with a visit to Canterbury Cathedral. Overnight Canterbury Cathedral Lodge.
- Walking for the day: 7.2 mi / 11.5 km
- Accommodation: Canterbury Cathedral Lodge in Canterbury or similar
Day 6: Departure
Extra night available upon request.
What to Expect
Accommodation is in nice hotels, B&Bs, guesthouses and inns, en-suite. We have carefully hand-picked all places and regularly monitor their quality. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour. Sometimes it may be necessary to book a bed and breakfast with shared bathrooms, but we would liaise with you to explain why and give you other options (i.e an upgrade to a better hotel) if no other accommodation was available.
Click to view our default hotels for this trip
- Ship & Trades in Chatham
- The Black Horse Inn in Thurnham
- Dog & Bear in Lenham
- Woolpack Inn in Chilham
- Canterbury Cathedral Lodge in Canterbury
*Hotels are subject to availability. In case a hotel is fully booked for your desired dates, we will replace it with a property of equal standard. We will provide full accommodation details upon booking confirmation.
Accommodation is on a bed & breakfast basis. Picnic lunches are optional at an extra charge and can be ordered locally. You can have dinner at your hotel or at nearby restaurants.
Difficulty & terrain
Easy to moderate walks – nothing strenuous if you can walk the distances concerned (read more about difficulty grades). 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 April to September. Accommodation will be difficult to obtain on UK national holidays unless booked well in advance. 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.
Click to view travel options and route planner
London Airports are the most convenient for reaching the start point of Rochester.
By train or bus
- Direct trains from London Victoria and London Bridge to Rochester train station take approx 45 mins. Trains also run to Rochester from other locations.
- From Canterbury, trains can be taken for onwards travel to London (approx 1-hour journey) or other destinations.
- For more information, tickets and timetables, please visit TimesLink & National Rail.
- 5 overnights en-suite, as detailed in the itinerary
- 5 breakfasts
- Luggage transfer when changing hotels (one piece of luggage per person, max 20 kg)
- Detailed route notes and maps (1 set per booking)
- 24/7 phone assistance by our local office/representative
- 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
Options, extras & supplements
- Single room supplement for members of a group
- This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
- Extra nights are available upon request