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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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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
  • £139
  • 16 charities
  • Sat 17 May
  • £139
  • 16 charities
Weymouth, Dorset, UK

Jurassic Coast Ultra Challenge | 2nd Half

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
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
  • £25
  • Sun 18 May
  • £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
  • £25
  • Sun 18 May
  • £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
  • £65
  • Sun 18 May
  • £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
A varied 56km challenge, initially following the path of the River Thames, before exploring the North Downs en route to the finish at Turners Hill and a huge celebration!
  • Sat 24 May
  • £139
  • 14 charities
  • Sat 24 May
  • £139
  • 14 charities
Richmond, UK

London 2 Brighton Ultra Challenge | 1st Half

A varied 56km challenge, initially following the path of the River Thames, before exploring the North Downs en route to the finish at Turners Hill and a huge celebration!

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 56 km trail running + 800 m ascent
Leafy Richmond to sunny Brighton – over the North Downs and the South Downs, with some wonderful Surrey and Sussex countryside in between, fully supported all the way with a huge celebratory finish!
  • Sat 24 May
  • £199
  • 14 charities
  • Sat 24 May
  • £199
  • 14 charities
Richmond, UK

London 2 Brighton Ultra Challenge | Full 100km Continuous

Leafy Richmond to sunny Brighton – over the North Downs and the South Downs, with some wonderful Surrey and Sussex countryside in between, fully supported all the way with a huge celebratory finish!

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 1500 m ascent
Leafy Richmond to sunny Brighton, over the North and South Downs, with some wonderful Surrey and Sussex countryside - all in daylight hours and with a good nights' sleep mid-way!
  • Sat 24 - Sun 25 May
  • £199
  • 14 charities
  • Sat 24 - Sun 25 May
  • £199
  • 14 charities
Richmond, UK

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

Leafy Richmond to sunny Brighton, over the North and South Downs, with some wonderful Surrey and Sussex countryside - all in daylight hours and with a good nights' sleep mid-way!

  • Chip timing
  • Enter online
  • GPS tracking
  • 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
  • £89
  • 14 charities
  • Sat 24 May
  • £89
  • 14 charities
Richmond, UK

London 2 Brighton Ultra Challenge | 1st Quarter

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 + 200 m ascent
Starting at Oaks Park then following the fantastic 2nd 1/4 Challenge route to Tulley’s Farm in Turners Hill, and then over the South Downs to the finish line at Brighton Racecourse to a celebration!
  • Sat 24 - Sun 25 May
  • £169
  • 14 charities
  • Sat 24 - Sun 25 May
  • £169
  • 14 charities
Carshalton, UK

London 2 Brighton Ultra Challenge | 3/4 Challenge

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

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 75 km trail running + 1300 m ascent
A great challenge through the Surrey and Sussex countryside with a Sutton start and Turners Hill finish with full support and a great finish line celebration!
  • Sat 24 - Sun 25 May
  • £89
  • 14 charities
  • Sat 24 - Sun 25 May
  • £89
  • 14 charities
Carshalton, UK

London 2 Brighton Ultra Challenge | 2nd Quarter

A great challenge through the Surrey and Sussex countryside with a Sutton start and Turners Hill finish with full support and a great finish line celebration!

  • Enter online
  • Undulating
  • Hilly
  • Age 14 & over
  • 33 km trail running + 600 m ascent
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.
  • Sun 25 May
  • £89
  • 14 charities
  • Sun 25 May
  • £89
  • 14 charities
Brighton, East Sussex, UK

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
Take in the stunning sights of Bristol and step into serene nearby nature on the city's outskirts, as part of Bristol Walkfest - the city's month-long programme of all things walking!
  • Sat 31 May
  • £35
  • Sat 31 May
  • £35
Bristol, Somerset, UK

Walk Bristol | 20 Miles

Take in the stunning sights of Bristol and step into serene nearby nature on the city's outskirts, as part of Bristol Walkfest - the city's month-long programme of all things walking!

  • Enter online
  • Fundraising optional
  • Age 16 & over
  • 20 miles walking
Take in the stunning sights of Bristol and step into serene nearby nature on the city's outskirts, as part of Bristol Walkfest - the city's month-long programme of all things walking!
  • Sat 31 May
  • £30
  • Sat 31 May
  • £30
Bristol, Somerset, UK

Walk Bristol | 15 Miles

Take in the stunning sights of Bristol and step into serene nearby nature on the city's outskirts, as part of Bristol Walkfest - the city's month-long programme of all things walking!

  • Enter online
  • Undulating
  • Fundraising optional
  • Age 16 & over
  • 15 miles walking
Get ready to explore one of Scotland's oldest and most iconic resorts, nestled in the heart of Perthshire, experiencing breathtaking countryside, with rolling hills, lush woodlands and scenic trails.
  • Sat 31 May
  • £25
  • Sat 31 May
  • £25
Crieff, Perth and Kinross, UK

Pink Ribbon Walk Scotland | Crieff Hydro | 20 Mile

Get ready to explore one of Scotland's oldest and most iconic resorts, nestled in the heart of Perthshire, experiencing breathtaking countryside, with rolling hills, lush woodlands and scenic trails.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 20 miles walking
Entries closed
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
  • £45-£120
  • Entries closed
  • Sat 31 May
  • £45-£120
  • Entries closed
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
The 10km Nordic Walk takes a scenic route through some classic Lake District Landscapes, including the shores of Grasmere and Rydal, as you propel yourself along with your poles.
  • Sat 31 May
  • £30
  • Sat 31 May
  • £30
Ambleside, Cumbria, UK

Lake District Running Festival | Grasmere Gallop Nordic Walking Challenge

The 10km Nordic Walk takes a scenic route through some classic Lake District Landscapes, including the shores of Grasmere and Rydal, as you propel yourself along with your poles.

  • Enter online
  • Undulating
  • Age 15 & over
  • 10 km walking + 160 m ascent
  • Sat 3 - Mon 5 May
Wigton, Lake District National Park, UK

Hadrians Wall Challenge

  • 3 days trekking
  • Sun 4 May
Belfast, County Antrim, UK

Moy Park Belfast City Marathon Events | 8 Mile Walk

  • 8 miles walking
  • Sat 10 May
Marlborough, Wiltshire, UK

The Ridgeway 40 Walk

  • 40 miles walking
  • Sat 10 May
Norwich, Norfolk, UK

Trek 24 Norfolk | 24 Miles

  • 24 miles trekking
  • Sat 10 May
Norwich, Norfolk, UK

Trek 24 Norfolk | 24km

  • 24 km walking
  • Sat 17 May
Ambleside, Cumbria, UK

Cumbrian Challenge | The Tougher

  • 28 km hiking + 1700 m ascent
  • Sat 17 May
Ambleside, Cumbria, UK

Cumbrian Challenge | The Tough

  • 21 km hiking + 1400 m ascent
  • Sat 17 May
Derby, Derbyshire, UK

CosyChild Bike & Hike | Amble to Ashbourne

  • 20 miles walking
  • Sat 17 May
Ambleside, Cumbria, UK

Cumbrian Challenge | The Peak

  • 11 km hiking + 650 m ascent

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