Challenge walks in South East
Find challenge walks in South East in 2026/2027 - 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 9 May
- £25
Pink Ribbon Walk | Blenheim Palace and the Cotswolds | 20 Mile
Discover the magic of this World Heritage Site and explore England’s largest area of outstanding natural beauty in the Cotswolds countryside on this charming20-mile walking adventure.
- 20 miles walking
- Sat 16 - Sun 17 May
- £20-£30
Follow the Seagulls | Isle of Wight
Your chance to combine the beauty of the Isle of Wight Coastal Path with its sea views, glades and tall ridges, with your love of wild walking, and support those with brain cancer in each step.
- Charity walk 2
- Sun 24 May
- £89
Brighton Challenge
A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.
- 25 km trail running + 400 m ascent
- Sat 13 Jun
- £20-£25
Mighty Hikes | South Coast
Starting in Brighton, hike the South Downs Way along dramatic cliffs and rolling countryside, passing the Seven Sisters and Beachy Head to support people living with cancer.
- Charity hike 2
- Sat 13 Jun
- £20-£25
Mighty Hikes | Thames Path
Hike from Windsor along the peaceful Thames Path, following England’s most iconic river through beautiful countryside to support Macmillan’s vital work for people living with cancer.
- Charity hike 2
- Sat 1 Aug
- £49-£139
North Downs 50 Ultra Challenge
A fabulous challenge setting out from Guildford base camp on a looped route taking in some of the best of the Surrey hills, the North Downs Way, and the surrounding countryside.
- 50K ultra run
- Trail run 2
- 10K run
- Sat 5 - Sun 6 Sep
- £89-£199
South Coast Ultra Challenge
The South Downs National Park is a superb backdrop for a real challenge featuring Beachy Head, the Seven Sisters and the South Downs Way with a choice of distances from 25km right up to 100km!
- 100K ultra run 2
- Ultra run 2
- Trail run
- Fri 11 - Sun 13 Sep
- £39-£199
Thames Path Ultra Challenge
England’s greatest river provides a fantastic backdrop for an unforgettable 'festival' challenge weekend, with distances from 10km right up to 100km there’s a Thames Challenge for everyone!
- 100K ultra run 2
- 50K ultra run 2
- Trail run 4
- Charity walk 4
- Ultra run
- + 1 more race
- Sat 12 Sep
- £20-£25
Mighty Hikes | Cotswolds
Hike through the quintessentially English countryside of the Cotswolds, finishing with a spectacular view of the magnificent Blenheim Palace, to support people living with cancer.
- Charity hike 2
- Sat 26 Sep
- £49-£139
Chiltern 50 Ultra Challenge
A beautiful, end-of-season, looped challenge in some of the Chilterns' finest countryside, with historic trails, rolling hills, nature reserves and fantastic views with routes from 10km up to 50km.
- 50K ultra run
- Trail run
- 10K run
- Sat 10 Oct
- £49-£139
Kent Downs 50 Ultra Challenge
An end-of-season ultra challenge in the Garden of England with a looped route around the Kent Downs starting on the North Downs Way with picturesque scenery and full support all the way.
- 50K ultra run
- Trail run
- 10K run