The Pilgrims' Way — Winchester to Canterbury 5 Day Itinerary
Walk the The Pilgrims' Way — Winchester to Canterbury in 5 days with our detailed itinerary. Day 1: Winchester to Farnham; Day 2: Farnham to Reigate; Day 3: Reigate to Rochester; Day 4: Rochester to Canterbury. Find accommodation and tips for a 5-day pilgrimage through Hampshire, Surrey & Kent.
Walking the The Pilgrims' Way — Winchester to Canterbury in 5 days is a great option for pilgrims who want to cover the ~130 miles route at a steady pace. This 5-day itinerary splits the route into 5 walking days, with overnight stops at key towns along the way.
Each day covers moderate distances, giving you time to enjoy the sacred sites, churches and landscapes of the The Pilgrims' Way — Winchester to Canterbury while making steady progress toward your destination.
Day-by-day plan
Day 1: Walk from Winchester to Farnham, covering 10 miles + 11 miles + 11 miles. Leave Winchester Cathedral and follow the River Itchen east, with its water meadows and chalk stream, to the market town of New Alresford. Climb onto the downs by way of the old drovers' lanes and tracks to Alton, with its Norman church of St Lawrence. Continue east over the North Downs to Farnham, where the castle and the ruins of Waverley Abbey mark the county border.
Day 2: Walk from Farnham to Reigate, covering 12 miles + 13 miles + 8 miles. Walk the chalk hills of the North Downs above Guildford, passing through ancient woodlands to the town and its Norman castle. Follow the North Downs escarpment past the church of St Martha's Hill and above the Tillingbourne valley to Dorking. A shorter day over Box Hill and along the ridge with wide views south over the Weald to Reigate.
Day 3: Walk from Reigate to Rochester, covering 9 miles + 15 miles + 14 miles. Continue east along the downs through Merstham and Godstone to Oxted, keeping to the old Pilgrims' Way line. The longest stage: cross into Kent on the North Downs, passing above the Weald, to the village of Wrotham. Descend to the Medway valley and Rochester, with its Norman cathedral and castle and the long-vanished shrine of St William of Perth.
Day 4: Walk from Rochester to Canterbury, covering 15 miles + 12 miles. Follow the Pilgrims' Way east through the orchards and hop gardens of Kent to Faversham, home of the National Shrine of St Jude. The final stretch to Canterbury Cathedral — shrine of St Thomas Becket and the goal of the medieval pilgrimage, with St Augustine's Abbey and St Martin's Church on the edge of the city.
Accommodation for your 5-day walk
You'll need accommodation in Farnham, Reigate, Rochester, Canterbury for your overnight stops. Use our route planning tool to book pilgrim-friendly places to stay at each stage of your 5-day The Pilgrims' Way — Winchester to Canterbury itinerary.
Book well in advance, especially during summer months and weekends, as accommodation along the route can be limited.
Tips for a 5-day The Pilgrims' Way — Winchester to Canterbury
Start early each day to give yourself plenty of daylight hours. Pack light but bring essentials — waterproofs, a first aid kit, and a water bottle. Check the weather forecast before setting off, and always carry a map or GPX file as backup.
Frequently Asked Questions
Can I walk the The Pilgrims' Way — Winchester to Canterbury in 5 days?
Yes. Walking the The Pilgrims' Way — Winchester to Canterbury in 5 days means covering moderate daily distances. This itinerary splits the ~130 miles route into 5 stages with overnight stops.
Is a 5-day The Pilgrims' Way — Winchester to Canterbury walk suitable for beginners?
A 5-day walk allows a moderate pace with shorter daily distances, making it suitable for most walkers with a reasonable level of fitness.
Where do I stay on a 5-day The Pilgrims' Way — Winchester to Canterbury walk?
Plan overnight stops in Farnham, Reigate, Rochester, Canterbury. Use our route planning tool to book accommodation at each stage.
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