The Island’s Coastal Path with 106 km & 1,800+ metres of climb (clockwise) – makes the Full Challenge a tough one! There’s a Full 2 Day ‘Daylight’ option, 3/4, 1/2 and 1/4 Island Challenges also – a fantastic scenic Southern 50 km Challenge & the Medina 10 mile option in historic Cowes.
With regular ferries from Southampton, Portsmouth, or Lymington – and a range of on-Island transfers for foot passengers – there’s an Isle of Wight Challenge bank holiday weekend waiting for you!
Our Chale start looks over the dramatic coastline to the west, and the route follows the coast with ups & downs around past the ‘Needles’. Then it’s northwards to the halfway in historic Cowes – a welcome stop where a hot meal & a massage awaits. We head around to Ryde, Bembridge, and another major rest stop at Culver Down for some hot food – before the final stretch back into Chale. An epic Challenge!
106 km & ~1800 metres
Every 10-15km under marquees with support – toilets, massage, changing rooms, medics, rest areas, hot drinks, water & snacks & much more.
There’s optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join & exit. These include:
Chale – Friday Evening
There’s the ULTRA MARCH®category for walkers aiming to do 100 km in less than 24 hours (or 50 km in under 12 hrs). 8.30am start.
For 2026, there’s ULTRA TRAILBLAZERZ® for faster, competitive, runners with an eye on the clock and a ‘time goal’ of sub 13 hrs (male) & 14 hrs (female) for 100km+ on this Challenge. 6.45 am start.
Ultra Challenge® 50 km and 100 km events are fully ITRA-certified and officially recognised as UTMB Index races. 4 ITRA points available.
Day 1 – 52 km & ~900 metres
Day 2 – 54 km & ~900 metres
Day 1 – Saturday
Day 2 – Sunday
Every 10-15km under marquees with support – toilets, massage, changing rooms, medics, rest areas, hot drinks, water & snacks & much more.
There’s a full range of optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join and exit – and to provide flexible options for your planning. These include:
Chale – Friday evening
Cowes – Saturday evening
Ultra Challenge® 50 km and 100 km events are fully ITRA-certified and officially recognised as UTMB Index races. 2 ITRA points available each day.
See the full 106 km route and all the Island’s spectacular scenery views in daylight! There’s a camping option at the Cowes halfway for rest recovery – or book a local B&B if that’s more your style, and with a camp option at Chale on Friday also you can turn your challenge into an adventure! On Sunday as the sun starts to rise we set out on the 2nd half – all the way back to Chale, where it all began!
A perfect choice if you’ve done a Half Challenge before – and want to ‘up’ the distance without committing to a ‘Full’ option. The route is 3/4 of the Full Challenge – so starts at the Chale basecamp, heads around the fantastic southern section – on to Cowes, and then a final quarter to a finish line at Culver Down after a tough 82 km – with its stunning views over to Sandown & Shanklin beaches. Do it as a ‘continuous’ challenge – OR rest overnight after the 1st 52 km & camp at our Cowes basecamp (or hotel/ B&B) – and do the remaining quarter on Sunday morning – with plenty of time to then travel home!
82 km & ~1300 metres
Every 10-15km under marquees with support – toilets, massage, changing rooms, medics, rest areas, hot drinks, water & snacks & much more.
There’s optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join & exit. These include:
Chale – Friday evening
Cowes – Saturday evening
52 km & ~900 metres
Every 10-15 km under marquees with support – toilets, massage, changing rooms, medics, rest areas, hot drinks, water & snacks & much more.
There’s a of optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join and exit – and to provide flexible options for your planning. These include:
Chale – Friday evening
OR/ AND – Cowes – Saturday (camping also available Friday evening – with morning shuttle to start)
There’s the ULTRA MARCH®category for walkers aiming to do 100 km in less than 24 hours (or 50 km in under 12 hrs). 8.30am start.
For 2026, there’s ULTRA TRAILBLAZERZ® for faster, competitive, runners with an eye on the clock and a ‘time goal’ of sub 6 hrs (male) & 6.5 hrs (female) for 50km+ on this Challenge. 6.45am start.
Ultra Challenge® 50 km and 100 km events are fully ITRA-certified and officially recognised as UTMB Index races. 2 ITRA points available.
The first half of the Isle of Wight is stunning! Starting from Chale, you will take on 52 km along this scenic section of the Island. Setting out across the areas of natural beauty with great viewpoints from the southern cliffs to the Needles, you’ll climb 900 m, with stops along the way to keep you energised! Your finish line is at historic Cowes, where a big celebration, a medal, a sit down & hot meal awaits!
A fabulous stretch of the Island’s Coastal Path guiding you via sandy beaches and picturesque old villages. You’ll trek through the resorts of Sandown, Shanklin, and Ventnor on a tough challenge on the wonderful east coast of this terrific Island!
54 km & ~1000 metres
Every 10-15km under marquees with toilets, changing rooms, medics, rest areas, hot drinks, water & snacks and much more.
There’s a full range of optional parking & pre / post Challenge bus transfer services to make it easy to join and exit. These include:
Chale or Cowes – Saturday
50 km & ~ 1025 metres
Every 10-15 km under marquees with toilets, massage, changing rooms, medics, rest areas, hot drinks, water & snacks and much more.
There’s a full range of optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join and exit – and to provide flexible options for your planning. These include:
Chale – Friday evening or Saturday evening
A fantastic looped route setting out from the Chale basecamp, that gives you the best of the Island’s dramatic scenery along famous southern coastline to the iconic ‘Needles’ – for a Picnic lunch at halfway. The route then heads up on to the Tennyson Trail and the Worsley Trail with fantastic panoramic views as it loops back to the Chale basecamp. Perfect if you want fantastic scenery – a manageable 50km – and ideal to park at Chale or even camp with us!
Our 1st Quarter 25 km Challenge starting from the Chale basecamp gives you the best of the Island’s dramatic scenery along famous southern coastline – finishing near the iconic Needles, for a Picnic lunch. With a 1/4 – there’s plenty of time left for an evening celebration on the Island!
25 km & ~500 metres
Every 10-15km under marquees with toilets, changing rooms, medics, rest areas, hot drinks, water & snacks and much more.
There’s a full range of optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join and exit – and to provide flexible options for your planning. These include:
Chale – Friday evening
25 km & ~500 metres
Every 10-15km under marquees with toilets, changing rooms, medics, rest areas, hot drinks, water & snacks and much more.
There’s a full range of optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join and exit – and to provide flexible options for your planning. These include:
Chale – Saturday evening
A fabulous stretch of the Island’s coastline setting out on the Sunday morning from Culver Down – perched high up above the bay with fantastic views. It’s through the resorts of Sandown, Shanklin, and Ventnor (a rest stop here – with snacks & drinks) – before finishing 25 km later at our main basecamp in Chale where a celebration, medal and hot meal awaits.
Cowes, and its famous marinas, sit on the estuary of the River Madina – and if you’re staying in Cowes – and fancy a bit of a challenge – this could be perfect for you! Starting at our showground basecamp – you’ll follow the trails around the estuary, cross on the chain ferry – and really get a good feel for Cowes and its surrounding area. You finish back at the Cowes basecamp after arewarding 10 mile mini challenge!
10 miles – and quite flat
Every 10-15km under marquees with toilets, changing rooms, medics, rest areas, hot drinks, water & snacks and much more.
There’s a full range of optional parking & pre or post Challenge shuttle bus transfer services, to make it easy to join and exit – and to provide flexible options for your planning. These include:
Cowes -Friday evening
