The Highwayman Run

An epic mixed road and trail run across Henley hills steeped in Highwayman history!

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The Highwayman Sportive

A huge sportive style road ride through the picturesque and challenging lanes of the Chiltern Hills.

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The Highwayman Duathlon

Enter both events to compete in the unique two day Highwayman Duathlon

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A Fanastic Multi Sport Weekend in the Heart of Henley-On-Thames

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Salute to all the Highwaymen and women who rode and ran over the weekend! Results and times are now online in our results centre. Photos will be available both here and on our Facebook page during the day tomorrow (Tuesday).

Three Events in One Weekend

The Henley Highwayman weekend is made up of a fantastic bike event and an incredible hill run that you enter as individual events or together as the amazing Henley Highwayman Duathlon!


Enter the Highwayman Sportive as a standalone event, or as part of the Highwayman Duathlon. Choose from full, mid and short route options to give you your perfect ride!


Enter the Highwayman Run as a standalone event or as part of the Highwayman Duathlon. This hilly, mixed surface course makes for one of the toughest and most beautiful runs on the country! One, two or three lap options let you take on the run of your choice.


Enter both the bike and the run to take part in the amazing Highwayman Duathlon! Spread over two days, with a unique points system deciding the winners, the Highwayman Duathlon is open to all-comers, over all distances!

New for 2016 – 5km Run Event

The Highwayman is an event for everyone! The new 5km route option opens this amazing run up to all comers! Just reach for those trainers and take on the challenge! The 5km route shares the same closed road start from the Market Square with all the other distances, and carries you up onto the most scenic part of the course overlooking the town and the river. At the feed station on top of the hill, you’ll leave the longer distance runners and drop down onto the Fairmile to return to the finish line and complete Henley’s newest and best 5k run!

Sign up for the Henley Highwayman today!


“A unique event in the home of the original highwaymen”

From the town to the river and the rolling Chiltern Hills, The Henley Highwayman is a celebration of this finest corner of England and a dark and dashing chapter in it’s history!


“Compete with the elite, or challenge your personal best”

Elite or amateur, team or solo, age and gender categories, mix and match distances and disciplines. There are so many ways to take part in the Highwayman!


”Come for the sport; stay for the social”

Make a weekend of it! Stay in Henley, socialise with your fellow competitors and enjoy events, features and offers in selected town centre restaurants and establishments.

Event Location

Swiss Farm Camping, Marlow Rd, Henley-on-Thames, Oxfordshire RG9 2HY

Highwayman Event Centre

The Dark History of the Henley Hills

It’s hard to believe that the bright and friendly town of Henley-on-Thames has such as dark and infamous chapter in it’s history, but it was indeed once the home of the highwaymen who have given our event it’s name. Henley was once the first lock on the Thames, at a time when the river was the main artery for freight coming in from London and overseas. As such, it was the point at which valuable goods were unloaded to be moved on by coach, and thieves and brigands including the notorious Dick Turpin would take full adavatage of the hills and narrow lanes to watch and lie in wait for their prey.

The Highwayman Run takes you high across the top of No Man’s Hill, where you will enjoy beautiful views of the river. And it was this very vantage point that the Highwaymen would watch the boats unloading and plan their highway robberies. And on the Highwayman Sportive, you’ll find plenty more evidence of the areas dark and dashing local history in the place names: Gallowstree Common, Dead Man’s Lane, The Highwayman Inn and Pack and Prime Lane (where coaches would stop to pack and prime their weapons before entering the badlands). You’ll feel this rich and exciting history all around as you take part in the Henley Highwayman; maybe the echo of distant past hoof-beats will even spur you on to go that little bit faster!

Turpin’s Hideout

The Crooked Billet in Stoke Row was once the hideout of the most notorious highwayman of all, Dick Turpin, who was romantically linked to the landlord’s daughter, Bess.

Gentleman Rogues

Many highwayman were originally cavaliers who supported King Charles I in the Civil War. Finding themselves on the losing side, they turned to crime after their lands and money were taken from them,

Pack & Prime

Pack and Prime Lane in Henley was the point at which coach drivers and guards paused to pack and prime their weapons before continuing on the dangerous journey from Henley to Oxford.

Supporting Sue Ryder Nettlebed Hospice

£2 from every entry will go to support the incredible care Sue Ryder provide to patients and their families here in the local area.

The Highwayman Sportive

Epic Chilterns Bike Event
  • 62, 120 & 182km  Route options
  • Full Route Marking
  • Comprehensive Rider Support
  • Feed/Support Stations on route
  • Mapping & GPS Files
  • Electronic Rider Timing
  • Finish Line Results Screen
  • Finishers Medals

The Highwayman Hill Run

Challenging Road/Trail Run
  • 9, 17 & 25km  Route options
  • Full Route Marking
  • Closed Road Start
  • On Course Marshals
  • Feed/Support Station on Route
  • Electronic Timing
  • Finish Line Results Screen
  • Finishers Medals

The Highwayman Sportive

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The Highwayman Duathlon

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The Highwayman Run

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