Enjoy the sunrise over Pen y Fan as you ‘Hike for Hope’ on Mother’s DayFrom the first step to the summit, what better way to celebrate everything about your incredible mum or mother figure by seeing the sun rise at the top of the stunning Pen y Fan, followed by a celebratory drink and tasty...
Take on this Ultra Challenge and enjoy the historic city sights of Bath! Centred on this elegant historic city, take on a 50km Ultra, a testing 25km, or a sharp 10km challenge at your pace as a walk, jog or run and fundraise for Winston's Wish! From the Racecourse basecamp, 2,000 adventurers will head out...
Take in the sights of Windsor Castle and the surrounding countryside in this Easter challenge! Get active after the Easter holidays and take on a historic 50 km Ultra, a testing 25 km, or a sharp 10 km challenge at your pace as a walk, jog, or run - and fundraise for Winston's Wish! From...
Don your kilt and join #TeamWinston for the Glasgow Kiltwalk in 2026! Glasgow Kiltwalk is back for 2026 and due to popular demand, it will be another TWO DAY event on the 25 & 26 April. Every step you take will make a BIG difference for the charity you love the most with all fundraising...
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...
Join us for the Lake District Challenge and take on England's finest countryside! Take on England’s finest countryside at your pace as a walk, jog, or run – and fundraise for Winston's Wish! Challenge basecamp is in Kendal, and it’s a 100km looped route with a few tough hills to Ambleside; a halfway point by...
Don your kilt and join #TeamWinston for the Aberdeen Kiltwalk in 2026! Join us for another unforgettable day in the City and ‘Shire for Aberdeen Kiltwalk on 7 June. Every step you take will make a BIG difference for the charity you love the most with all fundraising going directly to Winston's Wish. “The Kiltwalk...
Take on the 3 peaks for Winston's Wish! Starting at Fort William, you will head off towards the first and highest peak – Ben Nevis. Next, it’s on to the Lake District to conquer Scafell Pike by night. Your final ascent takes place in Snowdonia National Park, where you’ll climb the mighty Snowdon! With a...
Take on Mount Snowdon at night for Winston's Wish! Trekking Mount Snowdon (1,085m) during the daytime forms a great challenge, but using torches to light your way and having the moon as your backdrop, summiting at night brings another sense of achievement to an already recognised charity trek. Seeing the sunrise across Snowdonia National Park...
From rolling hills to fantastic views, the Cotswold Way challenge has it all! Our Cirencester basecamp is the start of the 100 km looped route through the heart of the Cotswolds, providing a stunning setting for 2,000 or so adventurers to test themselves. Rolling hills, villages, footpaths and stunning views to take on at your...
Take on the North Yorks Challenge and enjoy stunning coastal sights as you fundraise for Winston's Wish! A basecamp in Scarborough and a stunning coastal and moorland challenge, which you can take it on at your pace as a walk, jog, or run – and fundraise for Winston's Wish! The route heads around the town...
Take on the fabulous Peak District alongside 3,000 adventurers! A basecamp in idyllic Bakewell will welcome 3,000 adventurers who will test themselves in the fabulous Peak District National Park. You can take it on at your pace as a walk, jog, or run – and fundraise for Winston's Wish! There’s a range of camping options...
Join us for this Ultra Challenge and take on the beautiful Gower Peninsula! Set in the stunning Gower Peninsula - famous for its golden beaches, limestone cliffs, wild moors, ridges, and woodlands – take on a challenge at your pace as a walk, jog, or run – and fundraise for Winston's Wish! There are weekend...
Take on the first Minehead section of the stunning 630 mile Coastal Path in this summer challenge! A fantastic ‘South West’ summer challenge, taking in the first Minehead section of the famous 630-mile Coastal Path, and a basecamp in the shadows of the impressive Dunster Castle. The 50km loop then heads over Exmoor with ups...
Join #TeamWinston for the fabulous North Downs Ultra Challenge! The North Downs provides a fabulous challenge from a Guildford basecamp, with a looped 50 km route which takes in some of the best of the Surrey hills and the surrounding countryside. You can take it on at your pace as a walk, jog, or run...
Don your kilt and join #TeamWinston for the Dundee Kiltwalk in 2026! Dundee Kiltwalk is back across North Fife and Dundee on 16 August – you don’t want to miss it. Every step you take will make a BIG difference for the charity you love the most with all fundraising going directly to Winston's Wish....
Explore the capital with Winston's Wish! Get your walking shoes on and explore some of the Capital’s less known historic areas with a tour of the ‘gateway to London’ along the Thames’s eastern section – and fundraise for Winston's Wish. Starting alongside the grandeur of Woolwich Barracks (short walk from Elizabeth Line, DLR, & Overground)...
Take on some of England's finest scenery in support of bereaved children in 2026! The South Downs National Park is a superb backdrop for 2,000 adventurers to take on a real challenge, and you can take it on at your pace as a walk, jog, or run – and fundraise for Winston's Wish! An Eastbourne...
Experience the capital under the moonlight whilst raising funds for Winston's Wish! Take on either a spirited Friday evening 10km or an energetic 10-mile looped route walk through the heart of London as darkness falls, and the Moon rises – and fundraise for Winston's Wish! The Oval Cricket Ground is the start / finish venue...
Join in and trek across the Capital taking in unrivalled views of the skyline, and historic landmarks. Join 2,500 walkers and trek 25 km across the Capital with unrivalled views of the skyline and landmarks – and you can fundraise for Winston's Wish! From a Putney Bridge start it’s East towards the City, zigzagging over...
Explore the unique history of London by taking on the Thames Path Ultra Challenge! England’s greatest river provides a fantastic backdrop for an unforgettable challenge, which you can take on at your pace as a walk, jog, or run – and fundraise for Winston's Wish! Over 3,000 adventurers will join the Putney Bridge start, and...
Don your kilt and join #TeamWinston for the Edinburgh Kiltwalk in 2026! Take big strides in 2026 and join #TeamWinston in the Scottish capital for Edinburgh Kiltwalk on 13 September. Every step you take will make a BIG difference for the charity you love the most with all fundraising going directly to Winston's Wish. “The...
Discover some of the best Chilterns countryside in 2026 and fundraise for Winston's Wish! A 50km looped challenge in some of the Chilterns finest countryside, with historic trails, rolling hills, nature reserves, with fantastic views. Join up to 2,000 adventurers and take it on at your pace as a walk, jog, or run - and...
End the season of Ultra Challenges in the 'Garden of England.' An end of season Ultra Challenge in the ‘Garden of England’. A basecamp near Maidstone, join up to 2,000 adventurers and you can take it on at your pace as a walk, jog, or run – and fundraise for Winston's Wish! The 50km looped...
Take on the spookiest Ultra Challenge yet! Why not risk a hair-raising hike around some of the City’s scary streets and historic haunts and raise money for Winston's Wish! Choose your distance, gather your bravest guys and ghouls to make up a team – or go it alone if you dare and meet up with...
Conquer one of the Seven Wonders of the World and raise vital funds for Winston’s Wish! 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...
Witness the sun rising over the ever-changing dunes of the Sahara as you fundraise for Winston’s Wish! Join in this long-weekend trek for Winston's Wish, as you experience the beauty of one of the most breathtaking and largest deserts in the world – The Sahara! The charity challenge is to trek for four days through...
