Save £30 per person on your 2026 adventure with code 30FOR30 - click here for more details
Pilgrims' Way

Pilgrims' Way

A 144-mile walking holiday from Winchester to Canterbury in the footsteps of pilgrims.

10 to 17 nights
145 miles
Moderate to Strenuous

From £1580 per person

Find your holiday

About this route

10 to 17 nights
145 miles
Moderate to Strenuous
2nd January to 24th December

From £1580 per person

Pilgrims' Way

Cross the south of England from Winchester to Canterbury on a 144-mile ancient pilgrimage route: the Pilgrims’ Way.

From the enormous cathedral at Winchester, the trail travels through welcoming rural communities and across the North Downs. It promises an approachable challenge with plenty of historic and religious buildings to visit along the way, building up to the UNESCO World Heritage Site at Canterbury Cathedral.

The Pilgrims’ Way departs Winchester on a series of quiet footpaths between rural villages, tracing St Swithun’s Way through the Itchen Valley and along the River Wey to Farnham.

From here, it shadows the North Downs Way all the way to Canterbury. The Pilgrims’ Way shuns some of the National Trail’s steeper climbs and higher-level paths in favour of a gentler mid-level walk beneath the shoulder of the North Downs escarpment, winding through woodland, chalk grassland and the occasional fragrant orchard. That’s not to say the route is without its climbs, with far-reaching views aplenty over the surrounding countryside.

Standard
Interactive
© Contours Walking Holidays Pilgrims' Way map
Winchester / Canterbury
145 miles (231 km)
2nd January to 24th December

Holiday highlights

Beginning and ending your walk at two stunning religious and historical sites: the longest medieval cathedral in the world at Winchester and an UNESCO World Heritage Site at Canterbury, comprising Canterbury Cathedral, St Augustine’s Abbey and St. Martin’s Church.

Matching the journey of medieval pilgrims step for step, town for town, with overnight stays at friendly settlements complete with historic architecture. Take in Guildford Castle, the Church of St Bartholomew at Otford, and the pretty timbered village of Chilham.

Clambering across the chalk downs, with stunning views from the chalk ridge and at Box Hill.

Available tours

Code Tour Duration Difficulty Price per person
PILGW1 From Winchester to Canterbury 10 nights, 9 days walking Strenuous £1580
PILGW2 From Winchester to Canterbury 13 nights, 12 days walking Demanding £2045
PILGW3 From Winchester to Canterbury 14 nights, 13 days walking Moderate / Demanding £2200
PILGW4 From Winchester to Canterbury 17 nights, 16 days walking Moderate £2665