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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Select an event for photos, video, route, location, reviews, entry fees and how to enter.
- Sun 10 May
- £55
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
- Fri 15 - Sun 17 May
- £30
- Early bird
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
- Fri 29 - Sun 31 May
- £10-£79
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.
- Ultra run
- Trail run 4
- Walking festival
- Fun run 2
- Half marathon
- Sat 30 May
- £35
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...
- 17 km trail running + 369 m ascent
- Sat 2 - Sun 3 May
- £39-£199
Isle of Wight Ultra Challenge
- Trail run 3
- 50K ultra run 3
- 100K ultra run 2
- Ultra run
- Sun 3 May
- £20
Three Forts Challenge | 5 Mile Trail Run
- 5 miles trail running + 553 ft ascent
- Sun 10 May
- £28-£42
The Rathfinny Run 10.7K and Half Marathon
- 10K run
- Half marathon
- Sat 16 - Sun 17 May
- £39-£199
Jurassic Coast Ultra Challenge
- Trail run 2
- 50K ultra run 2
- 100K ultra run 2
- Marathon
- Ultra run
- + 1 more race
- Sat 23 - Sun 24 May
- £89-£199
London 2 Brighton Ultra Challenge
- Trail run 3
- Ultra run 2
- Marathon
- 100K ultra run 2
- Sat 23 May
- £42-£44
Seven Sisters Half Marathon
- 13.1 miles trail running + 2057 ft ascent