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UK charity challenges

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Over the last few years, many of us have taken the opportunity to, instead of flying overseas, explore much of the United Kingdom. These four beautiful countries are steeped in myths and legends. With some of the world’s oldest monuments - many believed to have been constructed millennia before the Common Era – England, Ireland, Scotland and Wales hold mysteries and secrets that are just waiting for us to uncover.

Come and join us as we marvel at the Roman’s strength while trekking along Hadrian’s wall, discover the hidden mysteries of the Celts by following their ancient pilgrimage from Glastonbury to Stonehenge, and camp under the twinkling stars right in the midst of the Scottish Highlands!

Our UK challenges are designed to not only show the raw beauty and engrossing history of the Home Nations, but to also raise millions of pounds for charity, providing invaluable support to people all over the world.

Stonehenge

Stonehenge

'What a wonderful time I have had trekking from Glastonbury to Stonehenge with a group of like-minded pilgrims realising a dream. I can't overstate how much I enjoyed the whole experience! Beautiful scenery and wildlife, including hares, deer, red kites and more.

Doctor Julia, who joined as a participant, and the Challenge Leader, Theo, were incredible. He had obviously done an incredible amount of research beforehand so that we got the most out of the Challenge. Meeting up with Mark Corney made our tour of Stonehenge so much more informative and interesting than it would have been otherwise.

I would recommend Dream Challenges to anyone looking for adventure.'
- John, Glastonbury to Stonehenge UK charity challenge 2021 participant

7 results

The Regain London to Amsterdam Cycling Challenge 2022

The Regain London to Amsterdam Cycling Challenge 2022

Challenge yourself to cycle from London to Amsterdam in two epic days on this iconic bike ride for Regain! Our fast-paced challenge will take us through the quintessential English countryside and on to the Netherlands for stunning sea views and an awesome celebration in Amsterdam.

Ride
  • Sep ’22

UK, Holland

From £849

Challenge level: 5 out of 5

The Scottish West Highland Way Trek 2022

The Scottish West Highland Way Trek 2022

Discover the incredible natural beauty of the Scottish Highlands, taste whisky fresh from a local distillery and enjoy an optional first-class ride on the world-famous Jacobite Steam Train, aka. the Hogwarts Express, on our unbeatable Scottish adventure.

Trek
  • Sep ’22

UK

From £1,100

Challenge level: 4 out of 5

The Hadrian's Wall Trek 2022

The Hadrian's Wall Trek 2022

Hike alongside Hadrian’s Wall on this enthralling time warp of a trek. Following the rustic rural trail from Solway to Wallsend, we’ll roam alongside the sea, before winding inland through fields and forest on the line of the ancient Roman landmark.

Trek
  • Sep ’22

UK

From £1,100

Challenge level: 4 out of 5

The Glastonbury to Stonehenge Pilgrimage 4-Day Trek 2022

The Glastonbury to Stonehenge Pilgrimage 4-Day Trek 2022

Join us on an enthralling pre-historic pilgrimage following the ancient Celtic Way from Glastonbury to Stonehenge. This 90km challenge takes in iconic sites, gives us enthralling insight into the original pilgrimage and allows us to savour the panoramas of rolling countryside, iron-age hillforts and ancient architecture.

Trek
  • Sep ’22

UK

From £651

Challenge level: 3 out of 5

Women V Cancer Cycle Coast to Coast UK 2023

WOMEN-ONLY

Women V Cancer Cycle Coast to Coast UK 2023

Get ready for our epic new Women V Cancer challenge, cycling coast to coast across the UK! In two stunning, sweaty days, we’ll cycle from Workington to Tynemouth through some of the UK’s most spectacular scenery and raise vital funds for Breast Cancer Now, Jo’s Cervical Cancer Trust and Ovarian Cancer Action.

Ride
  • Jun ’23

UK

From £1,089

Challenge level: 4 out of 5

Ride the Night London 2023

WOMEN-ONLY

Ride the Night London 2023

Ride the Night London is back for 2023 and just like the past eight events, it's going to be epic! On one night, thousands of amazing ladies will unite to cycle 50km or 100km through London for people facing cancer and you should be there too!

Ride
  • Apr ’23

UK

From £145

Challenge level: 2 out of 5

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