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Trail runs in East Midlands in May 2026

Find trail runs in East Midlands in May 2026 - filter by date, location or category, display on a map or use the advanced search to find your perfect race.

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Select an event for photos, video, route, location, reviews, entry fees and how to enter.

A tough, but ever so rewarding, day/night out with views for miles! Start in daylight and if you keep going long enough you'll be in complete darkness!
  • Fri 8 May
  • £33.30-£39
Loughborough, Leicestershire

Bat Challenge

A tough, but ever so rewarding, day/night out with views for miles! Start in daylight and if you keep going long enough you'll be in complete darkness!

  • 6 hrs trail running
  • Beginner-friendly
  • Chip timing
  • Enter online
  • Traffic free
  • Event village
  • Park
  • Sustainability policy
  • Age 16 & over
Join a friendly, well-organised trail run, or enter all three events to complete 'The Quest'! Scenic routes, great atmosphere, and distances to suit every runner from beginner to seasoned racer.
  • Sat 9 - Sun 10 May
  • £20-£75
Corby, Northamptonshire

Run Rabbit Trail Festival

Join a friendly, well-organised trail run, or enter all three events to complete 'The Quest'! Scenic routes, great atmosphere, and distances to suit every runner from beginner to seasoned racer.

  • Trail run
  • 10K run
  • Half marathon
  • Ultra run
Entries close soon
  • Beginner-friendly
  • Entertainment
  • Music
  • Event village
  • Park
  • Rural
  • Age 15 & over
A selection of races with top reviews based in the village of Naseby famous for the Battle of Naseby in 1645. The ultra takes in Althorp, home of the Spencer family and Princess Diana's resting place.
  • Sun 10 May
  • £24-£60
Naseby, Northamptonshire

Shires and Spires

A selection of races with top reviews based in the village of Naseby famous for the Battle of Naseby in 1645. The ultra takes in Althorp, home of the Spencer family and Princess Diana's resting place.

  • 10K run
  • Half marathon
  • Marathon
  • Trail run
  • Ultra run
  • Beginner-friendly
  • Event village
  • Rural
  • Age 18 & over
Welcome to a 6-hour timed running event where you can run a 5K all the way up to an ultra marathon on an out-and-back route within the time limit, with fuel stations, medal and goody bag.
  • Sat 16 May
  • £26-£28
Lincoln, Lincolnshire

Lincolnshire Run

Welcome to a 6-hour timed running event where you can run a 5K all the way up to an ultra marathon on an out-and-back route within the time limit, with fuel stations, medal and goody bag.

  • 5K run
  • 10K run
  • Half marathon
  • Marathon
  • Ultra run
  • + 1 more race
  • Families
  • Beginner-friendly
  • Event village
  • Age 12 & over
Taking place at Sherwood Forest, Smash Sherwood is set to be a banger of a race! Expect mixed terrain, hills, loose surfaces and exposed tree roots as you experience the forest. Medal and T-shirt too!
  • Sun 17 May
  • FREE-£40
Mansfield, Nottinghamshire

Smash Sherwood

Taking place at Sherwood Forest, Smash Sherwood is set to be a banger of a race! Expect mixed terrain, hills, loose surfaces and exposed tree roots as you experience the forest. Medal and T-shirt too!

  • Fun run
  • 5K run
  • 10K run
  • Trail run
  • Families
  • Beginner-friendly
  • Event village
  • Age 4 & over
Run it your way, from 5k to ultra, at your own pace, on a looped scenic Northampton trails. Inclusive, flexible, and rewarded with an amazing medal every time.
  • Sat 23 May
  • £15-£34
Northampton, Northamptonshire

Catch Me If You Can | Northampton

Run it your way, from 5k to ultra, at your own pace, on a looped scenic Northampton trails. Inclusive, flexible, and rewarded with an amazing medal every time.

  • Trail run
  • 5K run
  • 10K run
  • Half marathon
  • Marathon
  • + 3 more races
  • Families
  • Beginner-friendly
  • Event village
  • All ages
Walk, jog or run! Choose your distance from 5K to ultra, enjoy stunning Washlands trails, and earn a well-deserved medal and goody bag.
  • Sun 24 May
  • £15-£34
Northampton, Northamptonshire

Slow and Steady Wins The Race | Northampton

Walk, jog or run! Choose your distance from 5K to ultra, enjoy stunning Washlands trails, and earn a well-deserved medal and goody bag.

  • Trail run
  • 5K run
  • 10K run
  • Half marathon
  • Marathon
  • + 3 more races
  • Families
  • Beginner-friendly
  • Event village
  • All ages
  • Sun 3 May
  • £25-£37
Hope Valley, Derbyshire

Castle & Cake Race

  • Trail run 2
  • Sat 9 May
  • £46-£53
Newark, Nottinghamshire

Dukeries 30/40

  • Trail run 2
  • Sat 9 May
  • £38-£40
Chesterfield, Derbyshire

Spire Ultra

  • 33 miles trail running
  • Fri 15 May
  • £18-£20
Lincoln, Lincolnshire

The Skelly Trail 10K

  • 10 km trail running
  • Sat 16 May
  • £33-£35
Matlock, Derbyshire

Ian Milne White Peak Marathon

  • 26.2 miles trail running
  • Sat 16 May
  • £30-£32
Matlock, Derbyshire

White Peak Half Marathon

  • 13.1 miles trail running + 800 ft ascent
  • Sat 16 May
  • £17-£19
Matlock, Derbyshire

Festival of Running Down in a Shot 10K

  • 10 km trail running + 372 m ascent
  • Sat 30 May
  • £10-£49
Bakewell, Derbyshire

The Maverick Peak District Trail

  • Trail run
  • 10K run
  • Half marathon
  • Sat 30 May
  • £89-£165
Bakewell, Derbyshire

The Maverick Peak District X-Trail

  • 50K ultra run
  • 100K ultra run

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