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Challenge walks in UK in May 2025

Find challenge walks near me in UK 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
Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.
  • Sat 10 May 2025
  • £25
  • Sat 10 May 2025
  • £25
Cromer, Norfolk, UK

Mighty Hikes | Norfolk Coast | Marathon

Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.

  • Enter online
  • Fundraising required
  • Flat
  • Traffic free
  • Age 14 & over
  • 26.1 miles hiking + 300.33 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
The finish line is unique to you: 24 hours after the mass start, the race shall stop and the Solo Runners and Teams furthest South on the National Trail, shall be declared winners.
  • Sat 10 - Sun 11 May 2025
  • £92.50-£145
  • Sat 10 - Sun 11 May 2025
  • £92.50-£145
Prestatyn, Clwyd, UK

24 Hours South - The Offa's Dyke Ultra

The finish line is unique to you: 24 hours after the mass start, the race shall stop and the Solo Runners and Teams furthest South on the National Trail, shall be declared winners.

  • Newcomers
  • Chip timing
  • Enter online
  • GPS tracking
  • Event village
  • Rural
  • Age 18 & over
  • 24 hrs trail running
Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.
  • Sun 11 May 2025
  • £20
  • Sun 11 May 2025
  • £20
Cromer, Norfolk, UK

Mighty Hikes | Norfolk Coast | Half Marathon

Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.

  • Enter online
  • Fundraising required
  • Flat
  • Traffic free
  • Age 14 & over
  • 14.3 miles hiking + 185.77 m ascent
The ultimate coast path challenge! Walk 60 miles of the South West Coast Path over 3 days and take in the breathtaking sights and soak up the camaraderie for Children’s Hospice South West.
  • Fri 16 - Sun 18 May 2025
  • £350
  • Fri 16 - Sun 18 May 2025
  • £350
Westward Ho!, Devon, UK

Incredible Hike

The ultimate coast path challenge! Walk 60 miles of the South West Coast Path over 3 days and take in the breathtaking sights and soak up the camaraderie for Children’s Hospice South West.

  • Enter online
  • Fundraising required
  • Undulating
  • Hilly
  • Traffic free
  • Rural
  • Coast
  • Age 18 & over
  • 60 miles hiking
Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.
  • Sat 17 May 2025
  • £25
  • Sat 17 May 2025
  • £25
Callander, Stirling, UK

Big Hike | The Trossachs | Marathon

Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Hilly
  • Age 16 & over
  • 26.2 miles hiking + 2000 ft ascent
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
58km of beautiful trail, with ups and downs giving over 1600m of ascent on a gorgeous coastal route which visits some of the highlights of the Jurassic Coast.
  • Sat 17 May 2025
  • 13 charities
  • Sat 17 May 2025
  • 13 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge | 1st Half charity places

58km of beautiful trail, with ups and downs giving over 1600m of ascent on a gorgeous coastal route which visits some of the highlights of the Jurassic Coast.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 58 km trail running + 1700 m ascent
A demanding challenge, taking on 100km along the UNESCO World Heritage Jurassic Coast, starting from Corfe Castle on a fully-supported challenge visiting the highlights of the region.
  • Sat 17 - Sun 18 May 2025
  • 13 charities
  • Sat 17 - Sun 18 May 2025
  • 13 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge | Full 100km continuous charity places

A demanding challenge, taking on 100km along the UNESCO World Heritage Jurassic Coast, starting from Corfe Castle on a fully-supported challenge visiting the highlights of the region.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 2300 m ascent
Take on the full 100km challenge across two days, to enjoy the entirety of the route during daylight, with camping options at the halfway Basecamp in Weymouth.
  • Sat 17 - Sun 18 May 2025
  • 13 charities
  • Sat 17 - Sun 18 May 2025
  • 13 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge | Full 100km over 2 days charity places

Take on the full 100km challenge across two days, to enjoy the entirety of the route during daylight, with camping options at the halfway Basecamp in Weymouth.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 2300 m ascent
A mid-level, circular hike over the three peaks surrounding Derwentwater Catbells, Walla Crag and Latrigg. Includes Full Weekend Festival Ticket in the price!
  • Sat 17 May 2025
  • £25-£55
  • Sat 17 May 2025
  • £25-£55
Keswick, Cumbria, UK

Keswick Mountain Festival 3 Peaks

A mid-level, circular hike over the three peaks surrounding Derwentwater Catbells, Walla Crag and Latrigg. Includes Full Weekend Festival Ticket in the price!

  • Families
  • Newcomers
  • Music
  • Chip timing
  • Enter online
  • Mountainous
  • Event village
  • Age 12 & over
  • 18 miles hiking + 1050 m ascent
The route is 3/4 of the Full Challenge – so starts at the Corfe Castle main start, takes in the fantastic 2nd 1/4 Challenge route to Weymouth, and then on to West Bay & the finish line at Bridport.
  • Sat 17 May 2025
  • 13 charities
  • Sat 17 May 2025
  • 13 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge | 3/4 Challenge charity places

The route is 3/4 of the Full Challenge – so starts at the Corfe Castle main start, takes in the fantastic 2nd 1/4 Challenge route to Weymouth, and then on to West Bay & the finish line at Bridport.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 76 km trail running
Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.
  • Sat 17 May 2025
  • £20
  • Sat 17 May 2025
  • £20
Callander, Stirling, UK

Big Hike | The Trossachs | Half Marathon

Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 13.1 miles hiking + 1100 ft ascent
A classic Jurassic challenge, starting from Corfe Castle, along the Purbeck Ridge to Durdle Door, where the undulating route leads to the finish at Weymouth
  • Sat 17 May 2025
  • 13 charities
  • Sat 17 May 2025
  • 13 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge | 2nd Quarter charity places

A classic Jurassic challenge, starting from Corfe Castle, along the Purbeck Ridge to Durdle Door, where the undulating route leads to the finish at Weymouth

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 14 & over
  • 34 km trail running + 1100 m ascent
A looped route which follows the Purbeck Way to Swanage, before returning along the coast, to finish at Church Knowle near Corfe Castle, for a well-deserved glass of fizz.
  • Sat 17 May 2025
  • 13 charities
  • Sat 17 May 2025
  • 13 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge | 1st Quarter charity places

A looped route which follows the Purbeck Way to Swanage, before returning along the coast, to finish at Church Knowle near Corfe Castle, for a well-deserved glass of fizz.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 600 m ascent
A marathon distance challenge departing from Weymouth, visiting Chesil Beach and the West Dorset Heritage Coast en route to the finish line at Bridport.
  • Sat 17 May 2025
  • 13 charities
  • Sat 17 May 2025
  • 13 charities
Weymouth, Dorset, UK

Jurassic Coast Ultra Challenge | 2nd Half charity places

A marathon distance challenge departing from Weymouth, visiting Chesil Beach and the West Dorset Heritage Coast en route to the finish line at Bridport.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 42 km trail running + 600 m ascent

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