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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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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 2026
  • £30
  • Early bird
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.

Early bird on now

  • Families
  • Venue accessible
  • Beginner-friendly
  • Dogs allowed at venue
  • Entertainment
  • Music
  • Enter online
  • Event village
  • Event expo
  • Park
  • Rural
  • Mountains
  • Sustainability policy
  • All ages
  • 5K run 2
  • 10K run
  • Half marathon
  • 50K ultra run
  • Fell run
  • + 14 more races
A weekend of inclusive trail races, camping, festival vibes, yoga workshops, guided runs, live music and outdoor cinema, all based in the grounds of the iconic Blair Castle in the Cairngorms.
  • Fri 29 - Sun 31 May 2026
  • £10-£79
Pitlochry, Perth and Kinross, UK

Blair Castle Trail Weekender

A weekend of inclusive trail races, camping, festival vibes, yoga workshops, guided runs, live music and outdoor cinema, all based in the grounds of the iconic Blair Castle in the Cairngorms.

  • Families
  • Recycling
  • Beginner-friendly
  • Plastic bottle free
  • Entertainment
  • Music
  • Event village
  • Event expo
  • Park
  • Rural
  • Mountains
  • Sustainability policy
  • Public transport links
  • All ages
  • Ultra run
  • Trail run 4
  • Walking festival
  • Half marathon
A 17K trail run as part of the Lake District Running Festival in an iconic location with a grandstand finish, wooden medal, free event photos and, more importantly, cake...
  • Sat 30 May 2026
  • £35
Ambleside, Cumbria, UK

Lake District Running Festival | Grasmere Gallop 17km Trail Run

A 17K trail run as part of the Lake District Running Festival in an iconic location with a grandstand finish, wooden medal, free event photos and, more importantly, cake...

  • Hilly
  • Age 17 & over
  • 17 km trail running + 369 m ascent
  • Sun 3 May 2026
Lancing, West Sussex, UK

Three Forts Challenge | 5 Mile Trail Run

  • 5 miles trail running + 553 ft ascent
  • Sat 9 May 2026
Chesham, Buckinghamshire, UK

Chiltern Hills 100K

  • 100 km trail running
  • Sat 16 - Sun 17 May 2026
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge

  • Trail run 2
  • 50K ultra run 2
  • 100K ultra run 2
  • Marathon
  • Ultra run
  • + 1 more race
  • Sat 23 May 2026
Eastbourne, East Sussex, UK

Seven Sisters Half Marathon

  • 13.1 miles trail running + 2057 ft ascent

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