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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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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
Climb from valley to summit on a guided hill-challenge up Box Hill and surrounding area, tackling steep woodland trails and gritty elevation in one of southern England’s toughest guided trail runs.
  • Sun 3 May
  • £19
Dorking, Surrey, UK

Box Hill Vertical KM

Climb from valley to summit on a guided hill-challenge up Box Hill and surrounding area, tackling steep woodland trails and gritty elevation in one of southern England’s toughest guided trail runs.

  • 12.5 miles trail running + 1000 m ascent
  • Beginner-friendly
  • Enter online
  • Hilly
  • Event village
  • Rural
  • Age 18 & over
A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.
  • Sun 24 May
  • £89
Brighton, East Sussex, UK

Brighton Challenge

A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.

  • 25 km trail running + 400 m ascent
  • Undulating
  • Hilly
  • Age 14 & over
  • 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

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