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Pilgrims' Way Trekker Plus Challenge Winchester to Canterbury (fully booked until mid September 2024)

Available from March to end of October

From £1875ex flights

From £2140ex flights

Enquire Now for availability
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Taking the St. Swithuns Way from Winchester to Farnham , and then the North Downs Way National Trail in Kent the modern pilgrim has a well way-marked route to follow; Ordnance Survey Maps in scales to suit walkers that clearly show the National Trail as well as sections of ancient trackway and the pilgrims’ way depicted in gothic typefaces, with a plethora of guidebooks describing both the geography and the history of the trail.  The historical origins and debate are set out by Derek Bright (founder of Walk Awhile) in his book ‘The Pilgrims’ Way; Fact & Fiction of an ancient trackway', published by The History Press.


This walk follows the River Itchen from Winchester then rises to higher ground out of the Wey Valley, and ascends and descends through two Areas of Outstanding Natural Beauty – the Surrey Hills AONB, and the Kent Downs AONB.  Many of the road signs along the way will depict the familiar scallop shell, the sign of St James, the patron saint of pilgrims.  You will pass timber framed medieval Inns and restaurants which have adopted names connected with pilgrimage or Chaucerian characters.


All our long distance walks are have flexible start dates, and accommodation is booked with walker friendly inns, guest houses and hotels, on or close to the route.  Outside the major towns in particular, accommodation is subject to availability and we will sometimes use accommodation providers in a nearby village.   We will also arrange accommodation on request to suit those wishing to walk the route over more, or fewer, days.  We have given an example of the typical itinerary below with some suggestions for alternative distances.  Walking distances 7 to 16 miles per day.  18 day holiday with  additional nights 7 to 12 miles per day.  Challenging - some steep ascents



This itinerary includes: ensuite accommodation in B&Bs, inns and hotels with breakfasts, daily luggage transfer, advice on GPS link for the route,fully marked up maps and guidebook


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 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. 



Regular Ferries from Bilbao,Caen and Cherbourg to Portsmouth.  Then train from Portsmouth Harbour to Winchester.  From Canterbury there are regular trains to Dover for the channel crossing to Calais



Wincester and Canterbury are on main train lines from London.  National Express Coach Services run regularly from London Victoria to Winchester and Canterbury. 


Day 1

Arrival in historic Winchester from where King Alfred ruled the Anglo-Saxon kingdom of Wessex. Your first nights accommodation is in good quality accommodation close to the city centre and choice of restaurants.  Allow time to explore Winchester, with its medieval cathedral, Great Hall and cobbled streets,

Level - strenuous and stamina needed

Day 2

Winchester to Alresford

Leave Winchester and follow the St Swithuns Way, through the Itchen Valley, much admired by William Cobbett, with views of the River Itchen, passing water meadows and watercress fields to New Alresford, with its beautiful Georgian houses. (10 miles)  

Winchester to Canterbury Map

Day 3

Alresford to Alton

Continue along the St. Swithuns Way from Alresford to the market town of Alton.   Shortly before your destination you will reach Jane Austen’s House and museum at Chawton (13 miles)

Day 4

Alton to Farnham

Alton to historic Farnham passing by woods, vineyards and hop picking territory. Situated directly on the end of the St Swithun’s Way and the start of the North Downs Way.  Farnham Castle has many surviving features from Norman times,  was built by Bishop Henry de Blois, and the home of the Bishops of Winchester for nearly 300 years. (10 miles)

Day 5

Farnham to Guildford

Commencing your journey through the Surrey Hills, and continuing through hop country, pretty villages, woodland, water meadows and past St Catherine's  chapel, where a pilgrims fair was held in medieval times, then onto the banks of the River Wey to the bustling and ancient town of Guildford.(14 miles)

Day 6

Guildford to Dorking

Taking in lovely views of the South Downs, perhaps stopping for refreshments at the Newlands Corner beauty spot, then through forest tracks, on over chalk grassland and through holloways.  Shortly before Dorking you will pass extensive vineyards. (10 miles)

Day 7

Dorking to Reigate

Crossing the River Mole by the stepping stones, and then climbing Box Hill for the extensive views from the summit, (fortunately there is a café and tables at the top for refreshment), then continuing on through the Surrey Hills before descending to Reigate.  (9 miles)

River Mole.JPG

Day 8

Reigate to Tatsfield/Westerham

In the morning you ascend Reigate Hill and on to Gatton Park, then through Merstham where stone was quarried to build Windsor Castle.  You will reach the Caterham Viewpoint and  Botley Hill, the highest point on the North Downs Way and on to Oxted Downs.  (14 miles)

Day 9
Westerham to Otford

The walk continues with views of the Darent Valley, and through woods full of bluebells in the spring. You continue through woodland and downland, and catch glimpses of Chevening House, the residence of successive government ministers for the last 45 years, and currently the country home of the Foreign Secretary.  (10 miles)

Day 10
 Otford to Wrotham

You can take a short detour to Kemsing, known for St. Edith’s Holy Well, and a frequent stopping place for medieval pilgrims . There is a peaceful Kent Wildlife Trust nature reserve for a picnic. The overnight stay is in Wrotham associated with the journeys of medieval archbishops. 8 miles.  

Day 11
Wrotham to Rochester*.

This final stretch to Rochester* heads along the Pilgrims way offering fantastic views over the Medway Valley.  Shortly after passing by the village of Trottiscliffe you can make a short detour if you wish to the Neolithic megaliths known as the Coldrum stones.  Rochester is the second oldest diocese in England, with a fine Norman castle. 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.  (12 miles)

Optional choice of Aylesford Priory for overnight stay, rather than Rochester (12 miles)


Day 12
Rochester  or Aylesford to Thurnham

From Rochester* your walk continues through the Kent Downs Area of Outstanding Natural Beauty..  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.  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 to the ruins of the Norman Thurnham castle, with panoramic views, and then on to your evening accommodation  (12 miles)

*From Aylesford Priory to Thurnham (9 Miles)

Rochester Castle.jpg

Day 13
Thurnham to Lenham 

Following breakfast and luggage collection there is an optional 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.    Choice of  2 inns or independent restaurant in this small picturesque village.(11.5/9 or 6 miles)  *Accommodation can be arranged at Leeds Castle, subject to availability

AH-1676 Black Swans.jpg

Day 14
Lenham to Boughton Lees or Wye

Walk along ancient trackways and holloways to the market town of Wye, with detour to historic Charing for lunch. In Charing you can view the Archbishop’s Palace from the lane, 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 is said to mark the burial of the illegitimate son of Richard 111.

Accommodation is in a traditional inn on the North Downs Way, or in coaching inn in the heart of the old market town of Wye and close to other pubs and restaurants. (13 miles)

Lenham to Boughton Lees (10 miles)

Day 15
Wye to Chilham

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.  Accommodation in centuries old inn. (8.5 or 6 miles)

Day 16
Chilham to Canterbury

On this final day follow the 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. (7.2 miles)


Day 17


Day for sightseeing, in this historic & vibrant city with optional extra nights accommodation bookable

This holiday can be completed in 15 days by combining some of the shorter stages

 Extend your stay 
per person per night
*Based on 2 people sharing. £50 single occupancy supplement

Enquire Now for availability
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