The Isle of Wight Challenge 2020

Team of four men cycling along the Isle of Wight coastline and smiling
  • Isle of Wight
  • July 10, 2020

The Isle of Wight Challenge 2020

Are you ready to take on the Isle of Wight Challenge for Regain?

Test your speed, strength and stamina on this awesome three-activity team event. We challenge you, in teams of four, to cycle 44 miles, trek the 12-mile Tennyson Trail and canoe 1.9 miles on the River Medina, all in one day.

Rising with the sun, you’ll kick off from the heart of the island for a stunning 25-mile cycle along country roads.

Next, you swap your bikes for boots and trek the circular 12-mile Tennyson Trail. This stunning route takes you through the forest and along the coast, with stunning views across the sea to Bournemouth.

Arriving back at the check-in base, you reunite with your bikes and pedal a final 19 miles to the River Medina.

It’s the last push now and you end the epic day in Canadian canoes, paddling approx. 1.9 miles to the finish line. (No equipment or experience necessary – the Dream Challenges team provides everything you need, including experienced canoeing guides, ready to help you out at the drop of a paddle.)

The Isle of Wight Challenge 2020 is organised by the fantastic specialist events company, Dream Challenges, who we’ve been working with for years and who are renowned for the brilliant support they give on their challenges, from the moment you sign up until the weeks after the event.

This extraordinary team challenge brings together people from all walks of life, willing to conquer a mighty feat for the charities closest to their heart and we would love for you to enter a team in support of Regain.

As an Open Challenge, there are two ways in which you can fund your participation.

After paying your non-refundable registration fee (£195) to secure your team’s place, you can choose:

  • Sponsorship – You can commit to raising the minimum sponsorship target (£1,500 per team of four) for Regain and we would use £700 of this money to cover your challenge costs. The rest of the money would then go directly towards our work supporting sports tetraplegics across the UK.


  • Self fund – You are also welcome to self fund and pay the challenge costs (£700 per team of four) yourself. We would then just ask you to raise as much as you can for Regain and/or make a personal donation, 100% of which would go directly towards our work.


The Challenge

Day 1 | Friday 10 July 2020 | Challenge briefing and registration

The excitement begins on the Friday evening before you take on the challenge on Saturday. Teams meet at the event base (to be confirmed) on the Isle of Wight for registration, which opens at 6pm.

The fab Dream Challenges guides then give you a (compulsory) challenge briefing at 7pm, with the full details of what’s in store for you tomorrow. Then you’re free to chill out, chat with other teams and get an early night to rest up for the big day!

Day 2 | Saturday 11 July 2020 | Challenge Day

Waking bright and early, you meet the other teams with your bikes at the starting point at the centre of the island. The Dream Challenges event leaders will set you off in staggered starts for your first ride of approx. 25 miles.

Cycling in your teams, you’ll follow a charming, clearly marked and marshalled route along quaint country roads, to your check-in point. Here, you leave your bikes with the Dream Team and tackle the Tennyson Trail on foot. This stunning circular walk amounts to approx. 12 miles and will take you right back to your check-in point – and your bikes!

Now it’s back in the saddle for another cycle, this time heading to the River Medina, where your final test of the day awaits.

Swapping your bikes for boats, you canoe an approx. 1.9 mile course down the river.

Don’t worry, you don’t need any canoeing experience or equipment, as the Dream Challenges team provide everything you need, including Canadian canoes and they’ll kit you up with buoyancy aids. Of course, there will also be qualified canoe instructors there the whole time to supervise, guide and help you out if you need.

Your Isle of Wight Challenge finishes as your team canoes across the finish line!