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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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Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in the City of Discovery over a challenging 20 mile route.
  • Sat 17 May 2025
  • 5 charities
  • Sat 17 May 2025
  • 5 charities
Dundee, Dundee City, UK

The Kiltwalk Dundee | Mighty Stride charity places

Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in the City of Discovery over a challenging 20 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 21.5 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
A high-level horseshoe walk on varied terrain around the stunning fells surrounding Derwentwater and the Borrowdale Valley for experienced hikers. Includes Full Weekend Festival Ticket in the price!
  • Sun 18 May 2025
  • £60-£65
  • Sun 18 May 2025
  • £60-£65
Keswick, Cumbria, UK

Keswick Mountain Festival 8 Peaks

A high-level horseshoe walk on varied terrain around the stunning fells surrounding Derwentwater and the Borrowdale Valley for experienced hikers. Includes Full Weekend Festival Ticket in the price!

  • Newcomers
  • Music
  • Chip timing
  • Enter online
  • Mountainous
  • Event village
  • Age 18 & over
  • 18 miles hiking + 1350 m ascent
Walk, jog or run the journey from Capital to Coast, over the North and South Downs. A fully supported challenge leaving Richmond-upon-Thames for the finish line at Brighton Racecourse.
  • Sat 24 May 2025
  • 13 charities
  • Sat 24 May 2025
  • 13 charities
Richmond, UK

London 2 Brighton Ultra Challenge | Full 100km continuous charity places

Walk, jog or run the journey from Capital to Coast, over the North and South Downs. A fully supported challenge leaving Richmond-upon-Thames for the finish line at Brighton Racecourse.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 1500 m ascent
Walk, jog or run the full 100km London to Brighton route, over two daytime sessions, with an overnight stop at the Basecamp at Turners Hill.
  • Sat 24 - Sun 25 May 2025
  • 13 charities
  • Sat 24 - Sun 25 May 2025
  • 13 charities
Richmond, UK

London 2 Brighton Ultra Challenge | Full 100km over 2 days charity places

Walk, jog or run the full 100km London to Brighton route, over two daytime sessions, with an overnight stop at the Basecamp at Turners Hill.

  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 100 km trail running + 1500 m ascent
Starting in leafy Richmond, follow the River Thames past Kingston along a scenic route, which arrives at the finish in Oaks Park for a BBQ lunch and celebration.
  • Sat 24 May 2025
  • 13 charities
  • Sat 24 May 2025
  • 13 charities
Richmond, UK

London 2 Brighton Ultra Challenge | 1st Quarter charity places

Starting in leafy Richmond, follow the River Thames past Kingston along a scenic route, which arrives at the finish in Oaks Park for a BBQ lunch and celebration.

  • Chip timing
  • Enter online
  • GPS tracking
  • Flat
  • Age 14 & over
  • 25 km trail running + 210 m ascent
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
Make a mountain of difference to people living with cancer. Beginning in the beautiful Greater Langdale valley in the Lake District, you will hike to the top of England's highest mountain - Scafell.
  • Sat 31 May 2025
  • £45-£120
  • Sat 31 May 2025
  • £45-£120
Ambleside, Cumbria, UK

Defeat the Peak | Scafell Pike by Day Challenge

Make a mountain of difference to people living with cancer. Beginning in the beautiful Greater Langdale valley in the Lake District, you will hike to the top of England's highest mountain - Scafell.

  • Enter online
  • Fundraising required
  • Mountainous
  • Traffic free
  • Rural
  • Mountains
  • Sustainability policy
  • Age 14 & over
  • 12 hrs hiking + 1500 m ascent
  • Sun 18 May 2025
Harrogate, North Yorkshire, UK

Nidderdale Charity Walk & Run | 22 Mile Walk

  • 22 miles walking
  • Sun 18 May 2025
Harrogate, North Yorkshire, UK

Nidderdale Charity Walk & Run | 26 Mile Walk

  • 26 miles walking
  • Sun 18 May 2025
Harrogate, North Yorkshire, UK

Nidderdale Charity Walk & Run | 18 Mile Walk

  • 18 miles walking
  • Sun 18 May 2025
Harrogate, North Yorkshire, UK

Nidderdale Charity Walk & Run | 15 Mile Walk

  • 15 miles walking

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