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 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
- 50% off
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
- Sat 13 Jun
- £20-£25
- 25% off
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
- 25% off
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
- Fri 11 - Sun 13 Sep
- £55-£75
Trailwalker
Are you Trailwalker strong? As a team of four, trek 100km non-stop across the South Downs in under 30 hours.
- 100 km trekking
- 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
- Sun 22 Mar
- £30
Y2Y North Downs Trek / Run | Marathon Walk
- 26.2 miles walking + 3025 ft ascent
- Sat 18 Apr
- £39-£139
Windsor 50 Ultra Challenge
- 50K ultra run
- Trail run
- 10K run
- 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
- Sat 1 Aug
- £49-£139
North Downs 50 Ultra Challenge
- 50K ultra run
- Trail run 2
- 10K run
- Sat 5 - Sun 6 Sep
- £89-£199
South Coast Ultra Challenge
- 100K ultra run 2
- Ultra run 2
- Trail run
- Fri 11 - Sun 13 Sep
- £39-£199
Thames Path Ultra Challenge
- 100K ultra run 2
- 50K ultra run 2
- Trail run 4
- Charity walk 4
- Ultra run
- + 1 more race
- Sat 26 Sep
- £49-£139
Chiltern 50 Ultra Challenge
- 50K ultra run
- Trail run
- 10K run
- Sat 10 Oct
- £49-£139
Kent Downs 50 Ultra Challenge
- 50K ultra run
- Trail run
- 10K run