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Trail runs in South East in May 2026

Find trail runs in South East 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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This Bank Holiday event is run as cheaply as possible in order for people to be able to build their numbers or simply to help people achieve their own goals at an affordable price.
  • Mon 4 May
  • £16-£27
Staines, Surrey, UK

Bank Holiday Madness May

This Bank Holiday event is run as cheaply as possible in order for people to be able to build their numbers or simply to help people achieve their own goals at an affordable price.

  • Trail run
  • 5K run
  • 10K run
  • Half marathon
  • Marathon
  • + 3 more races
  • Families
  • Beginner-friendly
  • Event village
  • All ages
The Magna Carta event are based in scenic Runnymede and right near the site where the treaty of Magna Carta was agreed by King John of England and signed on 15th June 1215.
  • Sat 9 May
  • £33-£55
Egham, Surrey, UK

Magna Carta Summer

The Magna Carta event are based in scenic Runnymede and right near the site where the treaty of Magna Carta was agreed by King John of England and signed on 15th June 1215.

  • 10K run
  • Half marathon
  • Marathon
  • Beginner-friendly
  • Event village
  • Age 16 & over
Come and join the Spring Lucky Dip Run! There is no set medal for this race; instead, you will get to choose your own from a selection of medals from past events!
  • Sun 10 May
  • £16-£35
Staines, Surrey, UK

The Spring Lucky Dip Run

Come and join the Spring Lucky Dip Run! There is no set medal for this race; instead, you will get to choose your own from a selection of medals from past events!

  • Trail run
  • 5K run
  • 10K run
  • Half marathon
  • Marathon
  • + 3 more races
  • Beginner-friendly
  • Event village
  • All ages
  • Fri 1 May
  • £16-£27
Egham, Surrey, UK

Midweek Chasing Numbers May

  • Trail run
  • 5K run
  • 10K run
  • Half marathon
  • Marathon
  • + 3 more races
  • Sat 2 - Sun 3 May
  • £39-£199
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge

  • Trail run 3
  • 50K ultra run 3
  • 100K ultra run 2
  • Ultra run
  • Sat 2 May
  • £45
Guildford, Surrey, UK

Greensand Way Ultra Run

  • 30 miles trail running
  • Sun 3 May
  • £20
Lancing, West Sussex, UK

Three Forts Challenge | 5 Mile Trail Run

  • 5 miles trail running + 553 ft ascent
  • Sun 3 May
  • £13-£39
Camberley, Surrey, UK

Run Frimley | 1 Mile Fun Run

  • 1 km trail running
  • Mon 4 May
  • £38-£56
Winchester, Hampshire, UK

BigWayRound - Winchester

  • Trail run 2
  • Marathon
  • 50K ultra run
  • Sat 9 - Sun 10 May
  • £35-£80
Reading, Berkshire, UK

Goring Gap Trails

  • Ultra run 2
  • Long distance walk
  • Short walk 2
  • Half marathon
  • Sat 9 May
  • £118-£120
Chesham, Buckinghamshire, UK

Chiltern Hills 100K

  • 100 km trail running
  • Sun 10 May
  • £28-£42
Polegate, East Sussex, UK

The Rathfinny Run 10.7K and Half Marathon

  • 10K run
  • Half marathon
  • Sat 23 - Sun 24 May
  • £89-£199
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge

  • Trail run 3
  • Ultra run 2
  • Marathon
  • 100K ultra run 2
  • Sat 23 May
  • £42-£44
Eastbourne, East Sussex, UK

Seven Sisters Half Marathon

  • 13.1 miles trail running + 2057 ft ascent
  • Mon 25 May
  • £32
Marlow, Buckinghamshire, UK

Rebellion 10K

  • 10 km trail running

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