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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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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.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Half charity places

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.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 52 km trail running + 1100 m ascent
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.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full continuous charity places

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.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 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.
  • Sat 3 - Sun 4 May 2025
  • 12 charities
  • Sat 3 - Sun 4 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full 2 day daylight charity places

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
A NEW looped route setting out from the Chale basecamp, that gives you the best of the Island’s dramatic scenery along famous southern coastline to the iconic ‘Needles’.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Southern Loop charity places

A NEW looped route setting out from the Chale basecamp, that gives you the best of the Island’s dramatic scenery along famous southern coastline to the iconic ‘Needles’.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 50 km trail running
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.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Quarter charity places

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.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 660 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.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Cowes, Isle of Wight, UK

Isle of Wight Ultra Challenge | 2nd Half charity places

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.

  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 54 km trail running + 980 m ascent
Starting at our showground basecamp – you’ll follow the trails around the estuary, cross on the chain ferry – and really get a good feel for Cowes and its surrounding area.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Medina 10 Mile charity places

Starting at our showground basecamp – you’ll follow the trails around the estuary, cross on the chain ferry – and really get a good feel for Cowes and its surrounding area.

  • Chip timing
  • Enter online
  • Flat
  • Undulating
  • Age 8 & over
  • 10 miles trail running
Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.
  • Sun 4 May 2025
  • 12 charities
  • Sun 4 May 2025
  • 12 charities
Sandown, Isle of Wight, UK

Isle of Wight Ultra Challenge | 4th Quarter charity places

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

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 480 m ascent
Help transform the future of breast cancer one step at a time at this iconic venue where you'll walk through beautiful woods and fields on a ramble-ready route then receive your medal!
  • Sat 10 May 2025
  • £25-£35
  • Sat 10 May 2025
  • £25-£35
Woodstock, Oxfordshire, UK

Pink Ribbon Walk | Blenheim Palace and the Cotswolds | 20 Mile

Help transform the future of breast cancer one step at a time at this iconic venue where you'll walk through beautiful woods and fields on a ramble-ready route then receive your medal!

  • Enter online
  • Fundraising required
  • Undulating
  • Age 16 & over
  • 20 miles walking
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!
  • Sat 17 May 2025
  • £20
  • Sat 17 May 2025
  • £20
Cowes, Isle of Wight, UK

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
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!
  • Sat 17 - Sun 18 May 2025
  • £30
  • Sat 17 - Sun 18 May 2025
  • £30
Cowes, Isle of Wight, UK

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
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.
  • Sun 18 May 2025
  • £25
  • Sun 18 May 2025
  • £25
Epsom, Surrey, UK

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
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.
  • Sun 18 May 2025
  • £25
  • Sun 18 May 2025
  • £25
Epsom, Surrey, UK

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
Starting at Oaks Park then following the fantastic 2nd 1/4 Challenge route to Tulley’s Farm in Turners Hill, and then on over the South Downs & the finish line at Brighton Racecourse.
  • Sat 24 - Sun 25 May 2025
  • 13 charities
  • Sat 24 - Sun 25 May 2025
  • 13 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge | 3/4 Challenge charity places

Starting at Oaks Park then following the fantastic 2nd 1/4 Challenge route to Tulley’s Farm in Turners Hill, and then on over the South Downs & the finish line at Brighton Racecourse.

  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 75 km trail running + 1300 m ascent
A great challenge through the Surrey & Sussex countryside – with a Sutton start and Turners Hill / Tulley’s Farm finish.
  • Sat 24 - Sun 25 May 2025
  • 13 charities
  • Sat 24 - Sun 25 May 2025
  • 13 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge | 2nd Quarter charity places

A great challenge through the Surrey & Sussex countryside – with a Sutton start and Turners Hill / Tulley’s Farm finish.

  • Enter online
  • Undulating
  • Hilly
  • Age 14 & over
  • 33 km trail running + 600 m ascent
A new 25 km 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.
  • Sun 25 May 2025
  • 13 charities
  • Sun 25 May 2025
  • 13 charities
Brighton, East Sussex, UK

Brighton Challenge charity places

A new 25 km 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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