Trekking

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  • Pen y Fan Hike for Hope

    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...

  • Bath Ultra Challenge - walkers at the start line

    Bath 50 Ultra Challenge

    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...

  • Windsor 50 Ultra Challenge

    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...

  • Glasgow Kiltwalk

    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...

  • People walking along the Isle of Wight coast

    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...

  • Jurassic Coast Ultra Challenge starter line

    Jurassic Coast Ultra Challenge

    Join 3,000 adventurers taking on the spectacular Jurassic Coast Ultra Challenge in 2026! Spectacular World Heritage coastline to take on at your pace as a walk, jog, or run –...

  • London to Bright Ultra Challenge at the finish line

    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....

  • Lake District Ultra Challenge

    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...

  • Aberdeen Kiltwalk

    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...

  • 3 Peaks Challenge from the top of the pikes

    National 3 Peaks Challenge

    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...

  • Snowdon at Night Trek

    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...

  • Cotswold Way Ultra Challenge at the start line

    Cotswold Way Ultra Challenge

    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...

  • North Yorks Ultra Challenge

    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...

  • Peak District Ultra Challenge

    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...

  • Gower Peninsula Ultra Challenge

    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,...

  • South West Coast 50 Ultra Challenge

    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...

  • North Downs 50 Ultra Challenge

    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...

  • Dundee Kiltwalk

    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...

  • London Summer Walk warm up

    London Summer Walk Ultra Challenge

    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...

  • South Coast Ultra Challenge finisher image

    South Coast Ultra Challenge

    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...

  • Thames Moonlight 10 Walk - Ultra Challenge

    Thames Moonlight 10 Walk

    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...

  • Yorkshire Three Peaks Challenge

    Take on this iconic mountain endurance challenge, conquering three of Yorkshire's highest peaks in a single day! You will tackle the magnificent Pen-y-ghent (694m), Whernside (736m) and Ingleborough (723m) in...

  • Thames Bridges Trek

    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...

  • Thames Path challenge at the start line

    Thames Path Ultra Challenge

    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...

  • Edinburgh Kiltwalk

    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....

  • Chiltern 50 Ultra Challenge

    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,...

  • Kent Downs 50 Ultra Challenge

    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...

  • Halloween Ultra Challenge

    London Halloween Walk Ultra Challenge

    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...

  • Great Wall of China Trek

    Great Wall of China Trek

    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...

  • Sahara Desert Trek

    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...

  • Kilimanjaro Trek

    Mount Kilimanjaro Trek

    Tick Mount Kilimanjaro off the bucket list and raise vital funds for Winston's Wish! Mount Kilimanjaro is a ‘bucket list’ event for many and one of the most impressive charity...