The Whittington Way

  • United Kingdom England, The Whittington Way, View from the Chiltern Way overlooking the Thames, Walkopedia
  • United Kingdom England, The Whittington Way, View over Gloucester from The Wysis Way as it crosses the Cotswolds, Walkopedia
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  • United Kingdom England, The Whittington Way, View across the White Horse at Uffington from the Ridgeway, Walkopedia
  • United Kingdom England, The Whittington Way, Ridgeway looking East, Walkopedia
  • United Kingdom England, The Whittington Way, The Grand Union Canal at the intersection with Three Bridges., Walkopedia
  • United Kingdom England, The Whittington Way, The Chiltern Way, Walkopedia
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  • United Kingdom England, The Whittington Way, Burnham Beeches and The Shakespeare Way, Walkopedia
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Key information: The Whittington Way

  • The Whittington Way winds from north-west of Gloucester to the City of London, the imagined route taken by Dick Whittington, who famously ended up as Mayor of London.
  • A recreation by Tom Sheldon, using existing paths. We love this creativity! As if one isn't enough, he's developed two versions!

Walkopedia rating

  • Walkopedia rating68
  • Beauty28
  • Natural interest13
  • Human interest14
  • Charisma13
  • Negative points0
  • Total rating68

Vital Statistics

  • Length: 168 miles
  • Maximum Altitude: NA
  • Level of Difficulty: Moderate
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The Whittington Way: View across the White Horse at Uffington from the Ridgeway - © Tom Sheldon

WALK SUMMARY

Walkopedia friend Tom Sheldon says:

"2023 was the 600th anniversary of Richard Whittington’s death. He was Mayor of London four times and Master of the Mercers’ Livery Company three times. It therefore seemed appropriate to recreate the walk that the young Dick might have taken, as an eleven year old boy, when he left home and set out for London (where the streets were reputed to be paved with gold) to seek his fame and fortune.

There are two claims for where Whittington was born. One is at Pauntley Court, Pauntley, Gloucestershire. The other a fortified house that no longer exists in Sollers Hope, Herefordshire.Whittington’s father owned both properties. At the time of Dick’s birth his father was an outlaw, either because of an unpaid debt, or because he had married without the King’s consent. To escape the reach of the sheriffs of Gloucestershire it is quite possible that the Whittington family
decamped from Pauntley Court to their house over the border in Sollers Hope.

We have therefore created two different routes retracing Whittington’s steps, the first arguably more scenic from Pauntley, the second, closer, we think, to the route that Whittington would haveactually taken.

Both routes use established footpaths and national trails and avoid main roads where possible. Neither of the two routes is waymarked but it is hoped that this might one day be possible.

The first route took 9 days to walk the 168 miles, an average of over 18.5 miles a day.

The alternative route also took 9 days to walk the 174 miles so an average of 19 miles per day.

Route One: Pauntley to London

Day 1 Pauntley to Gloucester started on minor footpaths until we joined the Wysis Way and Three Choirs Way at Taynton and then on into Gloucester a distance of 14.5 miles.

Day 2 Gloucester to Sapperton. The intention had been to get to Tarlton Bridge but I had underestimated the amount of up and down involved in crossing the Cotswolds. As it was it was still 18.5 miles of strenuous walking along the Wysis Way to Chalford which then joined with the Thames and Severn Way to Sapperton

Day 3 Sapperton to Stanton Fitzwarren. A long 26 mile day but generally flat without too many obstacles. From Sapperton we were on the Thames and Severn Way to the source of the Thames and from there the Thames Path eventually diverting to our overnight stop in Stanton Fitzwarren.

Day 4 Stanton Fitzwarren to Letcombe Regis. 19.5 miles starting on minor footpaths and then a hill climb at Ashbury to join the Ridgeway. Glorious views in all directions and then a descent off the Downs to Letcombe Regis and our overnight stop.

Day 5 Letcombe Regis to Goring on Thames. 16.5 miles, when, after ascending the Downs, we rejoined the Ridgeway which took us all the way into Goring.

Day 6 Goring to Henley in Thames. 18.5 miles along the Chiltern Way to Shiplake and then we rejoined the Thames Path into Henley.

Day 7 Henley on Thames to Burnham Beeches. 19 miles along the Thames Path to Cookham and then the Shakespeare Way to Burnham Beeches.

Day 8 Burnham Beeches to Brentford Lock. 21 miles along the Shakespeare Way to Yiewsley and then the Grand Union Canal to Brentford Lock.

Day 9 Brentford Lock to Mercers’ Hall (City of London). 14.5 miles mainly along the Thames Path.

See a map of the route here. https://explore.osmaps.com/route/21245250/whittington-way-updated-24th-may 

Route Two (the alternative route) Sollers Hope to London

Day 1 Sollers Hope to Kilcott. Climbing out of the hamlet we joined the Three Choirs Way and then walked to Kilcott a distance of 12 miles.

Day 2 Kilcott to Longford. We continued on the Three Choirs Way and then the Wysis Way until we arrived on the outskirts of Gloucester where we joined the start of the Gloucestershire Way to Longford a distance of 16.5 miles.

Day 3 Longford to Shipton Oliffe. We continued on the Gloucestershire Way skirting south of Cheltenham to Shipton Oliffe a distance of 20.5 miles.

Day 4 Shipton Oliffe to Shipton-under-Wychwood. From Shipton Oliffe we continued on the Gloucestershire Way to Bourton-on-the-Water where we joined the Oxfordshire Way to Shipton-under-Wychwood a distance of 21.5 miles.

Day 5 Shipton-under-Wychwood to Oxford. From Shipton-under-Wychwood we continued on the Oxfordshire Way to Charlbury. Soon after passing through Stonesfield we left the Oxfordshire Way and joined the Shakespeare Way through Woodstock and onto Oxford a distance of 21 miles.

Day 6 Oxford to Watlington. Passing through Oxford we continued on the Shakespeare Way to Watlington a distance of 20 miles.

Day 7 Watlington to Cookham. Leaving Watlington we continued on the Shakespeare Way to Marlow and then onto Cookham a distance of 24 miles.

Day 8 Cookham to Greenford. From Cokkham we continued on the Shakespeare Way to Love Green where we then diverted to Hillingdon and then onto Greenford a distance of 24 miles.

Day 9 Greenford to Mercers’ Hall (City of London). From Greenford we followed the Grand Union Canal towpath to Paddington, walked through Hyde Park and St James’ Park and then rejoined the Thames Path to Mercers’ Hall in the City of London a distance of 14.5 miles.


19th April 2026"

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The Whittington Way: Burnham Beeches and The Shakespeare Way - © Tom Sheldon

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The Whittington Way: View over Gloucester from The Wysis Way as it crosses the Cotswolds - © Tom Sheldon

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The Whittington Way: Ridgeway looking East - © Tom Sheldon...
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