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History of a Chilterns route

Dashwood Arms, Old Oxford Road, Piddington, High Wycombe, Buckinghamshire, HP14 3BH

  • 20 Sep 2026
  • | In person
  • | Pre-booking required
  • | Walk / Tour

A 2,000-year historical walk covering several routes up a Chilterns hill, 3 miles. The history includes a well-preserved medieval settlement, cattle droving, a turnpike (toll) road and more recently a road made using a fleet of tiny steam trains.

This walk starts and finishes at the village of Piddington near West Wycombe, Buckinghamshire, which was created entirely for the workers at a new chair factory. Four different routes have been made up the hill to the west of the village. One road may have been a possible French invasion route, plotted by King Charles II, the next was a turnpike road that was made too steep for traffic. At the top of the hill is a large well-preserved medieval settlement which was investigated by the police coroner. Hear about some of the 23 armed robberies that took place on the hill.

Timings

Sunday 20 September:
1000

Location & directions

Dashwood Arms, Old Oxford Road, Piddington, High Wycombe, Buckinghamshire, HP14 3BH

Directions:
Parking on Old Oxford Road along from the pub, please be careful not to block this bus route.
Contact on day:
Simon Cains
Telephone number:
+447767610659

Booking information

Pre-booking requirement:
Pre-booking required
Booking conditions:
Just to keep to a maximum of 12.
Booking contact name:
Simon Cains
Booking email:
[email protected]
Booking opens:
21 Jul 2026 12:00 AM
Booking closes:
18 Sep 2026 12:00 AM

Accessibility details

Need to be able to cross a 50mph road twice safely. Long hill climb of 90 metres ascent, 1 in 12 slope, but at a slow pace with plenty of stops. No stiles or kissing gates. Please keep dogs on leads, there is open access to fields with sheep, pheasants etc. The Dashwood Roadhouse pub should be open at 12, where we start and finish the walk. Booking advised for lunch. Before 12, the nearest public toilets are in West Wycombe HP14 3AH and Lane End HP14 3ES.

Additional information

Includes some social history ( small worker's village set up by the owner in 1903). History of the road network and the attempts to make an easier route up the hill. I will try to keep the explanations clear and interesting, not academic. I have written a book on this history, and have led these walks for several years.

Max number of people:
12
Estimated duration:
3 hour(s) 0 minute(s)

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