Walking the Pilgrims' Way:  Rochester to Canterbury


From £645pp
ex flights

6 or 7 
Available from March to end of October
Enquire Now for Availability
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You are about to embark on a 45 mile walk along the North Downs Way National Trail, between the historic cathedral cities of Rochester and Canterbury, and through the Kent Downs Area of Outstanding Natural Beauty. Much of your route coincides with the ancient trackway that ran across southern England from Winchester in the west of the country through to Canterbury in the east. In addition to many historical sites the mixture of chalk downland and native, deciduous woodland provides delightful walking, with interesting species of seasonal flowers including orchids, cowslips, scarlet pimpernel, and english bluebells . Moderate with some ascents



Day 1

Arrive in Rochester which is the second oldest diocese in England, with a fine Norman castle and cathedral founded in AD604.  Your first nights accommodation is in good quality B & B accommodation close to the town,  In the evening allow time to dine in a choice of restaurants surrounding the Norman castle grounds. Rochester has many connections with Charles Dickens and one can visit his summer house in Rochester High Street and Miss Haversham’s House from Great Expectations.  Alternatively stay at the historic Aylesford Priory, south of Rochester and close to the trail, and dine in the medieval Pilgrims' Hall.

Day 2

Luggage transfer following breakfast. In the morning the walk follows the National Trail to the Medway Gap and Kits Coty Neolithic burial chamber believed to have been built in the same era as Stonehenge. After lunch follow the North Downs ridge / Pilgrims’ Way to the ruins of the Norman Thurnham castle, with panoramic views, which has been suggested may have been built on the foundations of an earlier structure which was used to guard an ancient trackway over the ridge. Other commentators have also suggested that the site was in use as a watchtower during the Roman occupation. Your accommodation for the night is in walker friendly inn accommodation with a well rated restaurant, where a table will be booked for you (12 miles).


This itinerary includes: quality accommodation in inns and B&Bs,  with breakfasts, daily luggage transfer, fully marked up maps, advice on GPS link to the route, and guidebook.  Hotel accommodation upgrades are available on this route - please ask for details.  


Support and advice is available by phone from your tracker throughout the duration of your walk. After breakfast each day, your luggage will be transported to your next accommodation stop.  There is an optional debrief meeting at the end of your holiday.


Walk Awhile accommodates walkers at inns and pubs with accommodation, hotels and B&Bs. There are dozens of historic pubs along the route, where you can enjoy refreshments. 


Flights arrive/leave from Gatwick, Stansted and Heathrow Airport, with good links to St. Pancras International rail station. 



Dover Ferry Port in Kent connects to Calais by cross channel Ferry, from where trains can be taken to Ashford/Wye.



Canterbury and Rochester are on main train lines from St Pancras International. Ebbsfleet International Station is one stop from Rochester

Eurostar from Brussels, Paris and Lille to St. Pancras, and Ebbsfleet.  National Express Coach Services run regularly from London Victoria to Rochester and Canterbury, . 

Day 3

Following breakfast and luggage collection walk to Leeds Castle, which is considered to be the most beautiful castle in England, built by Henry I; a Palace of Henry VIII and home to the Queens of England for 300 years. Afternoon walk along ancient trackway to the medieval village of Lenham. (11 miles) Alternatively you can choose to take a taxi (included) to Leeds Castle and then walk to Lenham( 6 miles) or walk directly along the North Downs Way to Lenham, without visiting Leeds Castle ( 9 miles) Choice of 2 inns or independent restaurant in this small picturesque village.

Day 4

Optional visit to the Lenham tithe barn built in 1350 (by pre-arrangement only). Walk along ancient trackways and holloways to the market town of Wye, with detour to historic Charing for lunch. In Charing you can view (from the lane) the Archbishop’s Palace the last of the archiepiscopal palaces built along the old road before Canterbury. Passing through the grounds of Eastwell Manor you can visit the ruined church where a tomb in the graveyard marks the burial of the illegitimate son of Richard 111.

Accommodation in coaching inn in heart of the old market town of Wye and close to other pubs and restaurants. (10 miles).

Day 5

Luggage collection following breakfast. Visit Boughton Aluph church and Pilgrims’ Porch where Pilgrims met before ascending up the old drovers trail into King Wood. Follow Pilgrims Way through Kings Wood, looking out for wild deer and walk through the grounds of Godmersham Park where Jane Austen kept house for her brother and was inspirational for Mansfield Park. Walk through the medieval village of Chilham and its square which is often used for filming. Choice of inns or teahouse for refreshment stop in Chilham. After lunch follow Pilgrims Way to Canterbury visiting Bigbury Iron Age camp where Julius Caesar defeated the British tribes in 54 BC. Visit the village of Harbledown referred to by Chaucer in the Canterbury Tales and go to the Black Princes Well where Henry II commenced his penitent walk for his role in the death of Thomas Becket. Enter Canterbury through city walls and West Gate and stay in city centre close to the Cathedral. (13.5 miles)

Leeds Castle UK

 Extend your stay 
per person per night
*Based on 2 people sharing. £35 single occupancy supplement

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Day 6

Departure Day or Extend your stay for sightseeing