Transaid challenges riders to take on Isle of Wight adventure

19th November 2025

Transaid is inviting supporters from across the transport and logistics industry to saddle up for our next fundraising cycle challenge: a 217km ride from London to the Isle of Wight, taking place 14–17 May 2026.

The challenge will set off from Box Hill, a landmark climb featured in the London 2012 Olympics road race, before navigating 110km through the beautiful Surrey Hills countryside. Participants will enjoy a sustained climb up Leith Hill – the highest point in Surrey – before crossing the South Downs National Park to reach the Portsmouth to Fishbourne ferry, with just a short cycle remaining to reach the hotel.

Day two promises an unforgettable 107km loop around the Isle of Wight, a route long considered a bucket-list ride for UK cyclists. Participants will experience 107km of rugged island scenery and challenging climbs that pass through charming villages, chalk coastlines, wooded glens and historic sites, before returning to the hotel to celebrate the conclusion of the event.

Maddy Matheson, Head of Fundraising for Transaid, says: “As our shorter European rides have grown in popularity, we thought it would be a great opportunity to take on a route that is on so many people’s bucket list: the Isle of Wight loop. This is a ride that combines demanding ascents with breathtaking views and will offer our riders an unforgettable journey through some of England’s most scenic and historic landscapes.”

Cycle challenges have long been a staple of our fundraising income, helping to raise vital unrestricted funds that can be deployed to test new programmes that will improve road safety and access to healthcare.

Matheson adds: “In today’s climate, with international development funding under increasing pressure across the charity sector, events like this cycle challenge are essential to sustaining Transaid’s work and driving our life-saving programmes forward. We’re really excited about this ride, and we are determined to make this one of our most memorable UK cycling events yet.”

 

How to enter

We welcome entries from both teams and individuals. Click here to visit the Isle of Wight 2026 webpage with more information and the registration form.

• Registration fee: £149 per person
• Minimum fundraising target: £1,550
• Included: accommodation, meals and luggage transport
• Single room supplement: £295
• Non-cycling guest supplement: £500 total (sharing the cyclist’s room)

A return coach transfer to Dorking on 17 May is included, kindly sponsored by Lucketts Travel.

 

Looking for an international cycling adventure?

Riders preferring a 2026 adventure further afield are invited to sign up for Transaid’s next international adventure, Kilimanjaro to Coast 2026, which will run from 17-26 September. This challenge will see a team of riders pedal 454km from Mount Kilimanjaro to Pangani on the Tanzanian coast. Limited spaces remain, and as such Transaid is encouraging prompt registration.