26 Challenge walks in South East

Filter by date

Filter by place

Map view
Hike a marathon from Brighton to Eastbourne along the stunning South Downs Way, with spectacular views of unspoilt coastline from the chalk cliffs of Seven Sisters Country Park.
  • Sat 10 Jun
  • £25
  • Entries closed
Brighton, East Sussex, UK

Mighty Hikes | South Coast | Marathon

Hike a marathon from Brighton to Eastbourne along the stunning South Downs Way, with spectacular views of unspoilt coastline from the chalk cliffs of Seven Sisters Country Park.

  • Entries closed
  • 26 miles hiking + 3164 ft ascent
Hike a half marathon along the stunning South Downs Way towards Eastbourne, taking in spectacular views of the finest unspoilt coastline from the chalk cliffs of Seven Sisters Country Park.
  • Sun 11 Jun
  • £20
  • Entries closed
Polegate, East Sussex, UK

Mighty Hikes | South Coast | Half Marathon

Hike a half marathon along the stunning South Downs Way towards Eastbourne, taking in spectacular views of the finest unspoilt coastline from the chalk cliffs of Seven Sisters Country Park.

  • Entries closed
  • 13 miles hiking + 1625 ft ascent
Hike a marathon along the beautiful Thames Path from Windsor Racecourse to Henley, along the banks of the most iconic river in England.
  • Sat 15 Jul
  • £25
Windsor, Berkshire, UK

Mighty Hikes | Thames Path | Marathon

Hike a marathon along the beautiful Thames Path from Windsor Racecourse to Henley, along the banks of the most iconic river in England.

  • 26 miles hiking + 385 ft ascent
Hike a half marathon along the beautiful Thames Path from Windsor Racecourse, along the banks of the most iconic river in England.
  • Sun 16 Jul
  • £20
Windsor, Berkshire, UK

Mighty Hikes | Thames Path | Half Marathon

Hike a half marathon along the beautiful Thames Path from Windsor Racecourse, along the banks of the most iconic river in England.

  • 13 miles hiking + 240 ft ascent
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.
  • Sat 2 - Sun 3 Sep
  • £198
  • 8 charities
Polegate, East Sussex, UK

South Coast 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.

  • 100 km trail running + 2100 m ascent
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.
  • Sat 2 - Sun 3 Sep
  • £198
  • 8 charities
Polegate, East Sussex, UK

South Coast 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.

  • 100 km trail running + 2100 m ascent
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.
  • Sat 2 Sep
  • £129
  • 8 charities
Polegate, East Sussex, UK

South Coast 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.

  • 57 km trail running + 1250 m ascent
The first quarter option of the South Coast Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckmere Haven, over the South Downs to finish at Alfriston.
  • Sat 2 Sep
  • £79
  • 8 charities
Polegate, East Sussex, UK

South Coast Challenge | 1st Quarter

The first quarter option of the South Coast Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckmere Haven, over the South Downs to finish at Alfriston.

  • 25 km trail running + 660 m ascent
Explore one of the UK’s most beautiful National Parks with its pretty riverside paths, rolling hills, white coastal cliffs and the famous South Downs Way, with charity #TeamPassage.
  • Sat 2 Sep
  • £30
Lewes, East Sussex, UK

South Downs Trekathon | The Passage

Explore one of the UK’s most beautiful National Parks with its pretty riverside paths, rolling hills, white coastal cliffs and the famous South Downs Way, with charity #TeamPassage.

  • Sponsored walk
The second half option of the South Coast Challenge is a scenic ‘marathon plus’ adventure across the South Downs towards Arundel.
  • Sun 3 Sep
  • £129
  • 8 charities
Hove, East Sussex, UK

South Coast Challenge | 2nd Half

The second half option of the South Coast Challenge is a scenic ‘marathon plus’ adventure across the South Downs towards Arundel.

  • 43 km trail running + 850 m ascent
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.
  • Sun 10 Sep
  • £15-£129
  • 12 charities
Egham, Surrey, UK

Thames Path 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.

  • 50 km trail running + 150 m ascent
The third quarter option of the Thames Path Challenge from Runnymede of Magna Carta Fame following the meandering waterway to finish at Cookham.
  • Sun 10 Sep
  • £7.50-£79
  • 12 charities
Egham, Surrey, UK

Thames Path Challenge | 3rd Quarter

The third quarter option of the Thames Path Challenge from Runnymede of Magna Carta Fame following the meandering waterway to finish at Cookham.

  • 28 km trail running + 20 m ascent
The fourth quarter option of the Thames Path Challenge from Cookham along the meandering waterway to Henley-on-Thames, home of the regatta, to a fabulous celebration finish and family BBQ.
  • Sun 10 Sep
  • £7.50-£79
  • 12 charities
Maidenhead, Berkshire, UK

Thames Path Challenge | 4th Quarter

The fourth quarter option of the Thames Path Challenge from Cookham along the meandering waterway to Henley-on-Thames, home of the regatta, to a fabulous celebration finish and family BBQ.

  • 22 km trail running + 10 m ascent
A beautiful 26-mile route along the River Thames featuring the picturesque Hardwick Estate and the Chiltern Way extension too, in support of Against Breast Cancer.
  • Sun 10 Sep
  • £10.80-£25.20
Wallingford, Oxfordshire, UK

Breast Walk Ever | Oxfordshire | Marathon

A beautiful 26-mile route along the River Thames featuring the picturesque Hardwick Estate and the Chiltern Way extension too, in support of Against Breast Cancer.

  • 26 miles hiking
A beautiful 13-mile route along the River Thames featuring the picturesque town of Goring-on-Thames in support of Against Breast Cancer.
  • Sun 10 Sep
  • £10.80-£22.50
Wallingford, Oxfordshire, UK

Breast Walk Ever | Oxfordshire | Half Marathon

A beautiful 13-mile route along the River Thames featuring the picturesque town of Goring-on-Thames in support of Against Breast Cancer.

  • 13 miles
The full distance option of the Chiltern 50 Challenge from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village.
  • Sat 23 Sep
  • £129
  • 6 charities
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Challenge | Full 50km

The full distance option of the Chiltern 50 Challenge from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village.

  • 50 km trail running + 920 m ascent
The first half option of the Chiltern 50 Challenge from Henley along some of the most picturesque parts of the Chiltern Way to Lewknor to finish with a celebration lunch.
  • Sat 23 Sep
  • £79
  • 6 charities
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Challenge | 1st Half

The first half option of the Chiltern 50 Challenge from Henley along some of the most picturesque parts of the Chiltern Way to Lewknor to finish with a celebration lunch.

  • 25 km trail running + 400 m ascent
The shorter 25km loop option of the Chiltern 50 Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village.
  • Sat 23 Sep
  • £79
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Challenge | 25km Loop

The shorter 25km loop option of the Chiltern 50 Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village.

  • 25 km trail running + 500 m ascent
The second half option of the Chiltern 50 Challenge from Lewknor to Henley by the Chiltern Hills and through the pretty village of Hambleden.
  • Sat 23 Sep
  • £79
  • 6 charities
Watlington, Oxfordshire, UK

Chiltern 50 Challenge | 2nd Half

The second half option of the Chiltern 50 Challenge from Lewknor to Henley by the Chiltern Hills and through the pretty village of Hambleden.

  • 25 km trail running + 500 m ascent
50 Miles. 2 Days. On Foot. 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!
  • Sat 13 Apr 2024
  • £20
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight

50 Miles. 2 Days. On Foot. 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!

  • Challenge walk
An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.
  • Sun 5 May 2024
  • £198
  • 7 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | Full 106km continuous

An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.

  • 106 km multi terrain running + 1960 m ascent
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.
  • Sun 5 - Mon 6 May 2024
  • £198
  • 7 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | Full 106km over 2 days

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.

  • 106 km multi terrain running + 1960 m ascent
Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.
  • Sun 5 May 2024
  • £79
  • 7 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | 1st Quarter

Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.

  • 25 km trail running + 660 m ascent
The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.
  • Sun 5 May 2024
  • £129
  • 7 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | 1st Half

The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.

  • 54 km trail running + 1100 m ascent
Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.
  • Mon 6 May 2024
  • £129
  • 7 charities
Cowes, Isle of Wight, UK

Isle of Wight Challenge | 2nd Half

Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.

  • 52 km trail running + 980 m ascent
Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.
  • Mon 6 May 2024
  • £79
  • 7 charities
Sandown, Isle of Wight, UK

Isle of Wight Challenge | 4th Quarter

Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.

  • 25 km trail running + 480 m ascent