Challenge walks in South East in May 2025
Find challenge walks near me in South East in May 2025 - search by date or place, display on a map or use the advanced search to find your perfect race.
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- Sat 3 May
- £139
- Sat 3 May
- £139
Isle of Wight Ultra Challenge | 1st Half
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.
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 52 km trail running + 900 m ascent
- Sat 3 May
- £199
- Sat 3 May
- £199
Isle of Wight Ultra Challenge | Full Continuous
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.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Hilly
- Age 18 & over
- 106 km multi terrain running + 1800 m ascent
- Sat 3 - Sun 4 May
- £199
- Sat 3 - Sun 4 May
- £199
Isle of Wight Ultra Challenge | Full 2 Day Daylight
The full 106km circumnavigation of the Isle of Wight, in daylight hours. Overnight at Cowes for a well-earned rest on this wonderful exploration of the coastal routes around the island.
- Chip timing
- Enter online
- Undulating
- Hilly
- Age 18 & over
- 106 km multi terrain running + 1960 m ascent
- Sat 3 May
- £139
- Sat 3 May
- £139
Isle of Wight Ultra Challenge | Southern 50
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.
- Chip timing
- Enter online
- Undulating
- Hilly
- Age 18 & over
- 50 km trail running + 1025 m ascent
- Sat 3 May
- £89
- Sat 3 May
- £89
Isle of Wight Ultra Challenge | 1st Quarter
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.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 14 & over
- 25 km trail running + 500 m ascent
- Sat 3 May
- £139
- Sat 3 May
- £139
Isle of Wight Ultra Challenge | 2nd Half
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.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Hilly
- Age 18 & over
- 54 km trail running + 1000 m ascent
- Sat 3 May
- £39
- Sat 3 May
- £39
Medina 10 Mile
Start at the showground basecamp and follow the trails around the estuary, cross on the chain ferry and get a good feel for Cowes and its surrounding area.
- Enter online
- Flat
- Age 8 & over
- 10 miles trail running
- Sun 4 May
- £89
- Sun 4 May
- £89
Isle of Wight Ultra Challenge | 4th Quarter
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.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 14 & over
- 25 km trail running + 500 m ascent
- Sat 10 May
- £25
- Entries close soon
- Sat 10 May
- £25
- Entries close soon
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 charming walking adventure.
- Enter online
- Fundraising required
- Undulating
- Age 13 & over
- 20 miles walking
- Sat 17 May
- £20
- Sat 17 May
- £20
Follow the Seagulls | Isle of Wight | One Day Challenge
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
- Enter online
- Fundraising required
- Undulating
- Age 18 & over
- 25 miles walking
- Sat 17 - Sun 18 May
- £30
- Sat 17 - Sun 18 May
- £30
Follow the Seagulls | Isle of Wight | Two Day Challenge
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
- Enter online
- Fundraising required
- Undulating
- Age 18 & over
- 50 miles walking
- Sun 18 May
- £25
- Sun 18 May
- £25
Poppy Hike | Medium
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
- Enter online
- Fundraising required
- Age 18 & over
- 15 miles walking
- Sun 18 May
- £25
- Sun 18 May
- £25
Poppy Hike | Long
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
- Enter online
- Fundraising required
- Age 18 & over
- 21 miles walking
- Sun 25 May
- £89
- Entries close tomorrow
- Sun 25 May
- £89
- Entries close tomorrow
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.
- Enter online
- Undulating
- Hilly
- Age 14 & over
- 25 km trail running + 400 m ascent