Challenge walks in South East
Find challenge walks near me in South East for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.
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Click an event for full event details, location, route, sustainability, what's included and how to enter.
- Sat 10 May
- £25
- Entries closed
- Sat 10 May
- £25
- Entries closed
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
- Sun 25 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.
- Enter online
- Undulating
- Hilly
- Age 14 & over
- 25 km trail running + 400 m ascent
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- Sat 7 Jun
- £25
- Sat 7 Jun
- £25
Mighty Hikes | South Coast | Marathon
Take on a challenge and join Macmillan at the South Coast Mighty Hike - where you’ll explore the stunning South Downs Way and take in spectacular coastal views to support people living with cancer.
- Enter online
- Fundraising required
- Hilly
- Age 14 & over
- 26.2 miles hiking + 964.73 m ascent
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- Sat 7 Jun
- £20
- Entries closed
- Sat 7 Jun
- £20
- Entries closed
Mighty Hikes | South Coast | Half Marathon
Take on a challenge and join Macmillan at the South Coast Mighty Hike - where you’ll explore the stunning South Downs Way and take in spectacular coastal views to support people living with cancer.
- Enter online
- Fundraising required
- Hilly
- Age 14 & over
- 13 miles hiking + 481.14 m ascent
- Sat 12 Jul
- £139
- 6 charities
- Sat 12 Jul
- £139
- 6 charities
North Downs 50 Ultra Challenge | 50km
Join a mid-summer North Downs 50 Challenge! This looped route is set in an area of outstanding natural beauty of the Surrey Hills, taking in chalk ridges and ancient woodlands.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 18 & over
- 50 km trail running + 830 m ascent
- Sat 12 Jul
- £89
- 7 charities
- Sat 12 Jul
- £89
- 7 charities
North Downs 50 Ultra Challenge | 25km Loop
The 25km looped challenge sets out from Guildford early Saturday morning, along some of the most picturesque parts of the Surrey Hills Way – with a rest stop at half way with snacks and drinks.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 14 & over
- 25 km trail running + 530 m ascent
- Sat 12 Jul
- £89
- 7 charities
- Sat 12 Jul
- £89
- 7 charities
North Downs 50 Ultra Challenge | 1st Half
Follow the North Downs Way to Dorking for a 24km challenge with fabulous views. You’ll get full support all the way, rest stops en route and a picnic lunch at the finish.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 14 & over
- 24 km trail running + 600 m ascent
- Sat 19 Jul
- £25
- Entries closed
- Sat 19 Jul
- £25
- Entries closed
Mighty Hikes | Cotswolds | Marathon
Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.
- Enter online
- Fundraising required
- Undulating
- Age 14 & over
- 25.24 miles hiking + 452.61 m ascent
- Sat 19 Jul
- £20
- Entries closed
- Sat 19 Jul
- £20
- Entries closed
Mighty Hikes | Cotswolds | Half Marathon
Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.
- Enter online
- Fundraising required
- Undulating
- Age 14 & over
- 13.38 miles hiking + 285.55 m ascent
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- Sat 26 Jul
- £25
- Sat 26 Jul
- £25
Mighty Hikes | Thames Path | Marathon
Take on a challenge and join Macmillan at the Thames Path Mighty Hike - where you'll hike from Eton College along the most iconic river in England to support people living with cancer.
- Enter online
- Fundraising required
- Flat
- Age 14 & over
- 25.4 miles hiking + 292.18 m ascent
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- Sat 26 Jul
- £20
- Entries closed
- Sat 26 Jul
- £20
- Entries closed
Mighty Hikes | Thames Path | Half Marathon
Take on a challenge and join Macmillan at the Thames Path Mighty Hike - where you'll hike from Eton College along the most iconic river in England to support people living with cancer.
- Enter online
- Fundraising required
- Flat
- Age 14 & over
- 13 miles hiking + 147.97 m ascent
- Sat 6 - Sun 7 Sep
- £199
- 15 charities
- Sat 6 - Sun 7 Sep
- £199
- 15 charities
South Coast Ultra Challenge | Full 100km continuous
The full distance option of the South Coast Challenge from sunny Eastbourne, over the magnificent Seven Sisters, onto Cuckmere Haven and over the South Downs all the way to historic Arundel.
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 100 km trail running + 2100 m ascent
- Sat 6 - Sun 7 Sep
- £199
- 14 charities
- Sat 6 - Sun 7 Sep
- £199
- 14 charities
South Coast Ultra Challenge | Full 100km over 2 days
The full distance option of the South Coast Challenge over 2 days with 57km on day 1 and 43km on day 2, meaning you experience the route in daylight with the chance to sleep overnight.
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 100 km trail running + 2100 m ascent
- Sat 6 Sep
- £139
- 15 charities
- Sat 6 Sep
- £139
- 15 charities
South Coast Ultra Challenge | 1st Half
The first half option of the South Coast Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckemere Haven, over the South Downs to finish via Brighton's promenade.
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 57 km trail running + 1250 m ascent
- Sat 6 Sep
- £89
- 15 charities
- Sat 6 Sep
- £89
- 15 charities
South Coast Ultra Challenge | 1st Quarter
The first quarter option of the South Coast Ultra Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckmere Haven, over the South Downs to finish at Alfriston for a celebration!
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 14 & over
- 25 km trail running + 660 m ascent
- Sat 6 - Sun 7 Sep
- £139
- 15 charities
- Sat 6 - Sun 7 Sep
- £139
- 15 charities
South Coast Ultra Challenge | 2nd Half
The second half option of the South Coast Ultra Challenge is a scenic ‘marathon plus’ adventure across the South Downs towards Arundel with wonderful coastal views and a celebratory finish!
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 43 km trail running + 850 m ascent
- Sat 13 Sep
- £169
- 18 charities
- Sat 13 Sep
- £169
- 18 charities
Thames Path Ultra Challenge | 3/4 Challenge
Start this epic 3/4 distance of the Thames Path Challenge near Hampton Court and follow the meandering waterway to Runnymede for a big celebration finish and hot meal at Henley on Thames.
- Chip timing
- Enter online
- GPS tracking
- Flat
- Age 18 & over
- 72 km trail running + 60 m ascent
- Sat 13 - Sun 14 Sep
- £139
- 18 charities
- Sat 13 - Sun 14 Sep
- £139
- 18 charities
Thames Path Ultra Challenge | 2nd Half
The second half option of the Thames Path Challenge from Runnymede along the meandering river through Cookham to Henley-on-Thames, home of the regatta, to a celebration finish and family BBQ!
- Chip timing
- Enter online
- GPS tracking
- Flat
- Age 18 & over
- 50 km trail running + 150 m ascent
- Sat 13 Sep
- £89
- 18 charities
- Sat 13 Sep
- £89
- 18 charities
Thames Path Ultra Challenge | 2nd Quarter
The second quarter event of the Thames Path Challenge takes a route from near Hampton Court and follows the meandering waterway to Runnymede of Magna Carta Fame, for a celebratory finish and hot meal!
- Chip timing
- Enter online
- Flat
- Age 14 & over
- 22 km trail running + 20 m ascent
- Sat 13 - Sun 14 Sep
- £89
- 18 charities
- Sat 13 - Sun 14 Sep
- £89
- 18 charities
Thames Path Ultra Challenge | 3rd Quarter
The epic third quarter option of the Thames Path Challenge starts from Runnymede of Magna Carta Fame following the meandering waterway to finish at Cookham to finish with a celebration and fizz at the
- Chip timing
- Enter online
- Flat
- Age 14 & over
- 28 km trail running + 20 m ascent