Discover some of the best of Chilterns countryside in 2025! A challenge event you can take on at your pace. The Chiltern 50 Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support including medics, marshals and...
From tough hills to fantastic views, the Cotswold Way challenge has it all! A challenge event you can take on at your pace. The Cotswold Way invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support including medics,...
Take on the fabulous Peak District alongside 2,000 adventurers! A challenge event you can take on at your pace. The Peak District Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support including medics, marshals and massage....
Join #TeamWinston for the fabulous North Downs Ultra Challenge! A challenge event you can take on at your pace. The North Downs 50 Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support including medics, marshals and...
Take on the brand-new Ultra Challenge in July 2025! A challenge event you can take on at your pace. The Brand New Gower Peninsula Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support including medics, marshals...
Take on the first Minehead section of the stunning and famous 630 mile Coastal Path for Winston's Wish! A challenge event you can take on at your pace. The South West Coast 50 Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink...
Explore the capital with Winston's Wish! Get active & explore some of the Capital’s historic areas with a tour of the ‘gateway to London’ along the Thames’s eastern section. Starting alongside the grandeur of Woolwich Royal Artillery Barracks (short walk from the new Elizabeth Line station!) – the full 50km looped route heads through Charlton,...
Take on some of England's finest scenery in support of bereaved children in 2025! A challenge event you can take on at your pace. The South Coast Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support...
Push yourself further by taking on the mighty Kilimanjaro Trek! Its snow-capped summit rises high above the dusty African plains; huge permanent glaciers flow down from the summit, spectacular views and beautiful ice formations are the reward for pushing our limits both physically and mentally on this, the mightiest of charity challenges. This trek which...
Explore the unique history of London by taking on the Thames Path Ultra Challenge! A challenge event you can take on at your pace. The Thames Path Ultra Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus...
Join 2,000 trekkers in an adventure across the capital! Join 2000 trekkers as we venture 25km across the Capital taking in unrivalled views of the skyline from its best vantage points. Follow a signed route, with free food and drink at regular rest stops, plus support including medics & marshals. Get the ‘Ultra Challenge’ support...
Don your kilt and join #TeamWinston for the Kiltwalk this September! Wander the scenic highlands and experience the fantastic atmosphere of Scotland’s largest walking event. “The Kiltwalk is one of those events that sticks with you – not just because of the challenge, but because of the people. Everyone’s doing their own little bit of...
Conquer one of the Seven Wonders of the World! The Great Wall of China has been voted one of the New Seven Wonders of the World. Stretching for 6,000km, it zig-zags its way across China, snaking across mountains and through valleys. The Great Wall of China Trek is a fantastic charity challenge hiking for five...
End the season of Ultra Challenges in the 'Garden of England.' A challenge event you can take on at your pace. The Kent Downs 50 Challenge invites you to walk, jog or run a distance of your choice, along a signed route, with free food and drink at regular rest stops, plus support including medics,...
Take on the spookiest Ultra Challenge yet! Why not treat yourself to a hair-raising hike around some of the City’s scary streets and historic haunts? Choose your distance, with 25km and 10km options, gather your bravest guys & ghouls to make up a team – or go it alone if you dare and meet up...
