Kilimanjaro Trek

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...

Tough Mudder

Will you dare to take on the epic Tough Mudder challenge? Test your endurance in the famed Tough Mudder challenge for Winston's Wish. This isn't your typical run. The Tough Mudder is built on a foundation of teamwork with an inspired obstacle course that is designed to test your strength, stamina and mental grit. Date: May...

Battersea Park Half Marathon

Beat your PB with Winston's Wish at the Battersea Park Half Marathon. Secure you place today and raise vital funds for bereaved children.

Great Wall of China Trek

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...

Kents Down 50 Ultra Challenge

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,...

Your Skydive challenge

Are you a thrill-seeker looking to take on a challenge and raise money for Winston’s Wish? We have just the thing. Book a skydive today and free-fall from 10,000 feet reaching speeds of up to 125mph, before the parachute opens and you gently glide back down to earth. It will be an experience you’ll never...

Vietnam to Cambodia Cycle

Take on a breath-taking bike ride in 2025! This breath-taking bike ride is one of the best in the world and will take us from Vietnam’s Ho Chi Minh City (Saigon) to the ancient temples of Angkor Wat in Cambodia. Registration fee: £299 Minimum sponsorship: £3,900 Before you start cycling we’ll have time to explore...

Milano Marathon

Join Team Winston for the Milano Marathon! The Wizz Air Milano Marathon returns on Sunday 12th April 2026 with an event that’s even richer, more inclusive, and more engaging: a true running festival that welcomes over 40,000 participants every year, including marathoners, relay teams, families, and running enthusiasts.At the heart of it all is Italy’s fastest...

Isle of Wight Ultra Challenge

Join us for the Isle of Wight Challenge and take on the island's costal path! Great challenges need great settings, and up to 2,000 adventurers will tackle the Isle of Wight’s stunning coastal path over the bank holiday weekend. Take it on at your pace as a walk, jog, or run - and fundraise for...

London 2 Brighton Ultra Challenge

Conquer the classic capital to coast route over the Bank Holiday weekend! 2,000 or so adventurers will take on the Capital to Coast trails and test their grit and determination. You can join and take it on at your pace as a walk, jog, or run - and fundraise for Winston's Wish! Richmond-Upon-Thames is the...