Chilterns races
Beech woods and chalk ridges an hour from London. Rolling rather than mountainous, and muddier than people expect.
Beech woods and chalk ridges within an hour of London, and much muddier than that description suggests. The classic Chilterns surface is leaf litter over chalk, which drains well in summer and turns to a slick paste through winter — the descents through the woods above Henley and Wendover catch people out every year.
The climbing comes in short, steep, repeated doses rather than long ascents. Wendover Woods in particular is a lapped course that finds far more ascent than the terrain looks capable of.
This is where a lot of people run their first fifty or hundred. The races are well marked, navigation is not usually part of the challenge, and the bases — Henley-on-Thames, Goring, Wendover — are easy to reach. Several run through the night, which in dense woodland means your world shrinks to the beam of your torch and route-finding becomes harder than the daylight version would suggest.
18 races
September 2026
1 raceOctober 2026
3 races4
Oct
2026
Marlow Donkey
Liston Hall, Marlow, Buckinghamshire · LDWA Thames Valley
A new Chilterns route each year from Marlow, centred on the Hambleden and Stonor valleys: 25k, 40k or a fiftieth-anniversary 50k. Limited to 150 and usually full by early September.
Entries open
£15–£20
17
Oct
2026
Autumn 100
Goring-on-Thames, Oxfordshire · Centurion Running
Four out-and-back spokes from Goring, a hundred miles in total.
EXPERT
Entries open
31
Oct
2026
Chiltern Ridge Winter 50K
Berkhamsted Cricket Club, Hertfordshire · Runaway Racing
The Chiltern Ridge loop in its winter form, fifty kilometres out of Berkhamsted and back.
VERY HARD
Entries open
November 2026
5 races7
Nov
2026
The Maverick Dark Oxfordshire Trail
Henley-on-Thames, Oxfordshire · Maverick Race
Stonor Park by head torch.
MODERATE TO HARD
Entries open
7
Nov
2026
The Maverick Oxfordshire Trail
Henley-on-Thames, Oxfordshire · Maverick Race
Stonor Park and the Chiltern beech woods.
MODERATE TO HARD
Entries open
14
Nov
2026
Wendover Woods 50
Wendover, Buckinghamshire · Centurion Running
Five laps of the steepest fifty miles Centurion put on.
EXPERT
Entries open
15
Nov
2026
Steppingley Step
Barton-le-Clay Village Hall, Bedfordshire · LDWA Beds, Bucks & Northants
Twenty-six, eighteen or twelve miles of field paths, tracks and woods through the Bedfordshire hills from Barton-le-Clay, with a start window and checkpoint times to plan around. Part of the group's triple challenge.
Entries open
£10–£15
21
Nov
2026
North Chilterns 50K
Offley, Hertfordshire · Runaway Racing
Fifty kilometres through the northern Chilterns in November, starting near Offley.
VERY HARD
Entries open
March 2027
2 races7
Mar
2027
Chiltern Kanter
Pitstone Memorial Hall, Buckinghamshire · LDWA Beds, Bucks & Northants
A map-reading event from Pitstone with questions to answer on the way: twenty-six, eighteen or thirteen miles of the Chilterns, all back by half six.
Entries open
20
Mar
2027
Hundred Hills 50km
Henley-on-Thames, Oxfordshire · Centurion Running
Fifty kilometres through the heart of the Chilterns.
VERY HARD
Entries open
April 2027
1 raceMay 2027
2 races29
May
2027
The Ridgeway Chase 60K
Ivinghoe Beacon, Buckinghamshire · Runaway Racing
Sixty kilometres of the Ridgeway from Ivinghoe Beacon, run on the same day as the full Challenge.
VERY HARD
Entries open
29
May
2027
The Ridgeway Challenge 86
Ivinghoe Beacon, Buckinghamshire · Runaway Racing
The whole Ridgeway in one go, a hundred and forty kilometres from Ivinghoe Beacon to Avebury.
EXPERT
Entries open
June 2027
1 raceJuly 2027
2 races4
Jul
2027
Chiltern Ridge Half Marathon
Wendover, Buckinghamshire · Runaway Racing
A half marathon along the Chiltern ridge from Wendover.
HARD
Entries open
10
Jul
2027
Race to the Stones
Lewknor, Oxfordshire · Threshold Trail Series
A hundred kilometres of the Ridgeway, Britain's oldest road, from Lewknor to the standing stones at Avebury — in one go or split over two days.
VERY HARD TO EXPERT
Entries open
October 2027
1 raceOther ways to look