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Hilly Ultra runs in South East in May 2026

Find hilly ultra 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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Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further this year!
  • Sat 2 - Sun 3 May
  • £39-£199
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further this year!

  • Trail run 3
  • 50K ultra run 3
  • 100K ultra run 2
  • Ultra run
  • Families
  • Beginner-friendly
  • Entertainment
  • Music
  • Event village
  • Age 14 & over
Take on a guided ultra trail adventure along the historic Greensand Way and stunning North Downs Way, through the Surrey Hills with sweeping views, ancient woodland and rewarding climbs.
  • Sat 2 May
  • £45
Guildford, Surrey, UK

Greensand Way Ultra Run

Take on a guided ultra trail adventure along the historic Greensand Way and stunning North Downs Way, through the Surrey Hills with sweeping views, ancient woodland and rewarding climbs.

  • 30 miles trail running
  • Beginner-friendly
  • Enter online
  • Hilly
  • Event village
  • Age 18 & over
  • Sat 9 May
  • £118-£120
Chesham, Buckinghamshire, UK

Chiltern Hills 100K

  • 100 km trail running

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