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  • 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...

  • 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...

  • 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...

  • 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...

  • 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...