Trail runs in South East in May 2026
Find 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.
Filter by place
Filter by date
This week
This weekend
Next week
Next weekend
Mar
Apr
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Spring
Summer
Autumn
Winter
All dates
Filter by category
MapEvent listings
Select an event for photos, video, route, location, reviews, entry fees and how to enter.
- Fri 1 May
- £15-£27
Midweek Chasing Numbers May
The aim of the midweek runs is to hold events as cheaply as possible in order for people to be able to build their numbers or simply to help people achieve their own goals at an affordable price.
- Trail run
- 5K run
- 10K run
- Half marathon
- Marathon
- + 3 more races
- 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
- 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
- Mon 4 May
- £15-£27
Bank Holiday Madness May
This Bank Holiday event is run as cheaply as possible in order for people to be able to build their numbers or simply to help people achieve their own goals at an affordable price.
- Trail run
- 5K run
- 10K run
- Half marathon
- Marathon
- + 3 more races
- Sat 9 May
- £33-£55
Magna Carta Summer
The Magna Carta event are based in scenic Runnymede and right near the site where the treaty of Magna Carta was agreed by King John of England and signed on 15th June 1215.
- 10K run
- Half marathon
- Marathon
- Sun 10 May
- £15-£35
The Spring Lucky Dip Run
Come and join the Spring Lucky Dip Run! There is no set medal for this race; instead, you will get to choose your own from a selection of medals from past events!
- Trail run
- 5K run
- 10K run
- Half marathon
- Marathon
- + 3 more races
- 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
- Mon 4 May
- £38-£56
BigWayRound - Winchester
- Trail run 2
- Marathon
- 50K ultra run
- Sat 9 - Sun 10 May
- £35-£80
Goring Gap Trails
- Ultra run 2
- Long distance walk
- Short walk 2
- Half marathon
- 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