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Hilly Trail runs in May 2026

Find hilly trail runs near me 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 stunning ultra trail race taking in the South West Coast Path on a fully-marked route with chip timing and eco medals for all, as part of the festival weekend!
  • Sun 10 May
  • £55
Kingsbridge, Devon, UK

Something Wild Festival | Summit Wild Ultra

A stunning ultra trail race taking in the South West Coast Path on a fully-marked route with chip timing and eco medals for all, as part of the festival weekend!

  • 50 km trail running
  • Chip timing
  • Enter online
  • Hilly
  • Age 18 & over
The UK's top outdoor sports festival! Incredible entertainment, sports events, speakers, live music, activities, brand expo, bars, food, drink and much more.
  • Fri 15 - Sun 17 May
  • £30
Keswick, Cumbria, UK

Keswick Mountain Festival

The UK's top outdoor sports festival! Incredible entertainment, sports events, speakers, live music, activities, brand expo, bars, food, drink and much more.

  • 5K run 2
  • 10K run
  • Half marathon
  • 50K ultra run
  • Fell run
  • + 14 more races
  • Families
  • Venue accessible
  • Beginner-friendly
  • Dogs allowed at venue
  • Entertainment
  • Music
  • Enter online
  • Event village
  • Event expo
  • Park
  • Rural
  • Mountains
  • Sustainability policy
  • All ages
Walk, jog or run along the spectacular UNESCO World Heritage coastline from Corfe Castle past Lulworth Cove and Durdle Door, with full support, welcoming base camp and finish line celebration!
  • Sat 16 - Sun 17 May
  • £39-£199
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge

Walk, jog or run along the spectacular UNESCO World Heritage coastline from Corfe Castle past Lulworth Cove and Durdle Door, with full support, welcoming base camp and finish line celebration!

  • Trail run 2
  • 50K ultra run 2
  • 100K ultra run 2
  • Marathon
  • Ultra run
  • + 1 more race
  • Families
  • Beginner-friendly
  • Entertainment
  • Music
  • Event village
  • Rural
  • Coast
  • Age 14 & over
Walk, jog or run the capital-to-coast route with 2,000 other adventurers over a range of distance options available and superb support all the way, for all abilities and experience levels.
  • Sat 23 - Sun 24 May
  • £89-£199
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge

Walk, jog or run the capital-to-coast route with 2,000 other adventurers over a range of distance options available and superb support all the way, for all abilities and experience levels.

  • Trail run 3
  • Ultra run 2
  • Marathon
  • 100K ultra run 2
  • Families
  • Beginner-friendly
  • Entertainment
  • Event village
  • 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
  • Fri 22 - Sun 24 May
  • £278-£300
Hull, East Yorkshire, UK

Hardmoors 200

  • 200 miles trail running
  • Sat 23 May
  • £42-£44
Eastbourne, East Sussex, UK

Seven Sisters Half Marathon

  • 13.1 miles trail running + 2057 ft ascent
  • Mon 25 May
  • £14-£16
Dursley, Gloucestershire, UK

Dursley Peaks Race

  • 10.31 km trail running
  • Sat 30 May
  • £35
Ambleside, Cumbria, UK

Lake District Running Festival | Grasmere Gallop 17km Trail Run

  • 17 km trail running + 369 m ascent

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