Over the past 15 years, our cycle challenges have seen over 550 riders conquer 17 bespoke events across 15 different countries, impressively amassing over £2 million for Transaid to date. Transaid’s cycle challenges provide invaluable unrestricted funding for our road safety and access to healthcare programmes – meaning we can provide funding where it is most needed. By taking part in a Transaid cycle challenge, you’re helping us and our partners to achieve the United Nations’ Sustainable Development Goals by 2030: to halve road traffic deaths and injuries, end the epidemic of malaria, and reduce the maternal mortality rate to less than 70 per 100,000 live births.

How can my company take part?

As well as entering a team to take on the challenge, you can support the challenge as a sponsor! We have multiple sponsorship packages available with excellent marketing opportunities for your company. If you are interested in sponsoring the challenge, please contact Anna at anna@transaid.org.

Fill out the registration form below to secure your place on Isle of Wight 2026 cycle challenge! For more information about the challenge or if you have questions, please contact Anna.

Want to sponsor this challenge?

We are seeking corporate sponsors to support Isle of Wight 2026, with excellent marketing opportunities available in three packages. Click here for the Sponsorship Pack.

Isle of Wight 2026

Our 2026 Transaid European Cycle Challenge takes us on one of the UK’s most celebrated cycling routes — a full circumnavigation of the isle of Wight, offering breathtaking sea views, charming seaside towns, and exhilarating climbs.

14th May 2026
Surrey and Isle of Wight, UK
Registration fee: £149

Additional Information

The challenge begins on the outskirts of London in Dorking, right at the foot of the legendary Box Hill. We’ll loop around and over this iconic climb before meandering through the scenic lanes of the Surrey Hills and on towards the rolling beauty of the South Downs National Park. As the landscape opens up, we’ll descend towards the South Coast, ready to board the Portsmouth to Fishbourne ferry. Once on the Isle of Wight, it’s a short, gentle ride to our hotel, which will be our home for the next two nights.

The Isle of Wight loop covers 106 kilometres of rugged coastline, the route delivers everything a cyclist could wish for: testing climbs, sweeping descents, and a constantly changing backdrop of seaside villages, chalk cliffs, wooded glens, and historic landmarks. Every turn offers another reason to fall in love with the island’s charm and natural beauty.

We’ll take on the full circumnavigation of the island from our base in Wootton Bridge, riding clockwise to experience the best of the coast before returning to the hotel in the evening. There, we’ll celebrate our incredible achievement with a well-earned group dinner and toast to the journey.

Dates: 14 – 17 May 2026
Duration: 4 days | Cycling: 2 days
Distance: 217 kilometres
Elevation: 2650 metres
Registration fee: £149
Minimum fundraising pledge: £1,550 (excluding gift aid and registration fee)

The cost includes riders’ twin share accommodation, cyclist ferry crossing from Portsmouth to Fishbourne on 15 May, lunch and refreshments on cycle days, dinner, vehicle and cycle support, luggage transfer, coach transfer from Portsmouth, bike transport from IoW to Dorking after the challenge, and GPX files.

Entries encouraged from individuals and teams alike.

You can find the full information pack here, or click the image.

Coach transfer from the Isle of Wight to Dorking kindly sponsored by:

Please contact anna@transaid.org for any questions.

Fill out the form below to register!

Over the past 15 years, our cycle challenges have seen over 550 riders conquer 17 bespoke events across 15 different countries, impressively amassing over £2 million for Transaid to date. Transaid’s cycle challenges provide invaluable unrestricted funding for our road safety and access to healthcare programmes – meaning we can provide funding where it is most needed.

By taking part in a Transaid cycle challenge, you’re helping us and our partners to achieve the United Nations’ Sustainable Development Goals by 2030: to halve road traffic deaths and injuries, end the epidemic of malaria, and reduce the maternal mortality rate to less than 70 per 100,000 live births.