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The Highwayman’s Trail

October 17 2026
Princess Risborough Oxon
Date Confirmed
Registration Opened: April 09 2026
 
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Distances: 39, 50, 72 km
Difficulty: Moderate terrain with rolling short steep hills or moderate, sustained climbs
Limited to: 2,000 or less Participants

The Highwayman’s Trail: Epic Autumn Gravel / MTB Riding!

The Chilterns are a near perfect mix of roads tracks and trails for gravel riding and MTB. The Highwayman’s Trail spins out its route to explore some of the darker, grittier folds of these deceptively demanding hills.

While the Chilterns might enjoy a genteel reputation today, their hidden history recalls them as a hotspot of dashing villainy. Coaches loaded with cargo from trading vessels that docked at Henley had to make their way through the wooded hills where robbers watched and waited. The truth of these robberies were usually far from the romantic image of the gentleman robbers we have today, making this part of the country a forbidding proposition for tradesmen and travellers.

And the very things that made this area perfect for highway robbery, make it ideal Gravel/MTB riding today. The densely folded and wooded hills conceal a network of lanes, tracks and trails the wind and climb and fall continuously, while the quintessentially English countryside views and picture postcard villages gracefully evoke tales from times past!

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Start Located At: Princes Risborough School, Merton Rd, Princess Risborough HP27 0DR
 
 
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0118 988 6041
 
Included

Choice of course distances
Full course marking
Detailed route map
Support vehicle / mechanical assistance on the course
Free CNP energy drink
Support/feed station on route (80& 60k only. Drinks station on 40k route)
Free allocation of energy snacks for each rider at support stations and finish
On site catering – Hot and cold food and drinks
Electronic rider timing
Immediate results for each rider at the finish with Bronze, Silver and Gold standards
Website results service

 
Facilities
Parking
Changing Rooms
 
Support for Participants
Route Signposted
SAG Wagon
 
Features
Course Timing
Results Within 24 Hours
Photos
Downloadable GPS files
 
Nutrition
Feed / Aid Stations
 
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