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Hilly Trail runs in South East in May 2026

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

  • 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
  • Sun 3 May
  • £20
Lancing, West Sussex, UK

Three Forts Challenge | 5 Mile Trail Run

  • 5 miles trail running + 553 ft ascent
  • 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 May
  • £42-£44
Eastbourne, East Sussex, UK

Seven Sisters Half Marathon

  • 13.1 miles trail running + 2057 ft ascent
  • Sun 24 May
  • £89
Brighton, East Sussex, UK

Brighton Challenge

  • 25 km trail running + 400 m ascent

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