Hilly Trail runs in UK in May 2026
Find hilly trail runs in UK 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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- Sat 2 - Sun 3 May
- £39-£199
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
- Sat 2 May
- £45
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
- Sat 2 May
- £40-£42
May the Fourth be with you (original) | Marathon
Take on a stunning, two-lap, trail marathon challenge across the Shropshire Hills, with epic scenery, and a rewarding finish earned mile by mile.
- 26.2 miles trail running + 4948 ft ascent
- Sun 3 May
- £19
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
- 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
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
- Sat 16 - Sun 17 May
- £39-£199
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
- Sat 23 - Sun 24 May
- £89-£199
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
- 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 23 May
- £42-£44
Seven Sisters Half Marathon
- 13.1 miles trail running + 2057 ft ascent
- Sat 30 May
- £35
Lake District Running Festival | Grasmere Gallop 17km Trail Run
- 17 km trail running + 369 m ascent