Running in circles: a trip around the Isle of Wight | Travel

If you said you were going round the Isle of Wight, most people would presume you were doing it in a boat. And I’ve done that – bobbing along in a day cruiser. I spent most of the time vomiting over the stern while everyone else swilled gin and tonics and marvelled at the island’s crumbling cliffs.

Last month, however, I took a very different route and ran the length of the island’s coastal path, as part of the Isle of Wight Challenge. When I entered, along with my friends Alan and Tom, I imagined it’d be the sort of eccentric and pointless adventure that would appeal to us and about a dozen other social misfits. In fact, we were joined at the start by 1,700 other runners and walkers. Who knew? The gun sounded at 8am on that blustery Saturday morning and all we had to do was follow the endless pink arrows until, eventually, we arrived back at the starting-point, having run 66 miles in a circle. Bonkers, of course, but to us completely blissful.

Living on the edge … Martin Love, right, with friends Tom and Alan on their run around the Isle of Wight

Before you head to the Isle of Wight, the cliche you hear is that it is like going back to the 1950s. Stepping off the ferry you can almost feel your pulse slowing and stress levels dropping. The place has its own distinct flavour and there is so much natural variety, from cliffs to rolling hills and sandy coves. It feels as if you are in an offshore Dorset or Hampshire, or even in the Peak District. Almost half the island is designated an Area of Outstanding Natural Beauty, but in sharp contrast an air of sleepy neglect hangs over some of the small towns – the posh marinas which punctuate the coast, bristling with masts, underline the fact that all that money is floating tantalisingly out of reach.

The isle is diamond shaped and our race began at the southern point near Chale. Next door is the bizarrely named Blackgang Chine, the UK’s oldest amusement park. It opened in 1843, but we didn’t have time to visit its Land of Imagination experience, as we are seeking our thrills elsewhere. Instead, off we trotted, heading west towards the Needles – the most recognisable landmark. We followed the precarious path along the collapsing cliffs. It felt like the sea was nibbling away at the island, one wave at a time. This area is known as the Back of the Wight and the sea-bruised cliffs are a palaeontologist’s dream, thronging with fossilised crocodiles and dinosaur skeletons.

Flower power: Freshwater Bay, where Jimi Hendrix performed in 1970 to a crowd of 600,000.

Flower power … Freshwater Bay, where Jimi Hendrix performed in 1970 to a crowd of 600,000. Photograph: Alamy

The trail led us on to more secure ground and across the flower-strewn fields of Freshwater. It’s here that the famous festival of 1970 was held. Jimi Hendrix performed in front of 600,000 hippies, before dying less than three weeks later. This time it was just us and some spaced-out cows.

Next we arrived on Tennyson Down – a spectacular, whale-backed ridge of chalk that rises to almost 500ft. The views are huge. The down is named after Alfred, Lord Tennyson, who lived nearby at Farringford House for almost 40 years. He used to walk here everyday, saying the air was worth “sixpence a pint”. Now it’s at least £4.50 a pint.

As a Victorian, the poet wasn’t alone in his fondness for the island. Charles Dickens wrote much of David Copperfield at Bonchurch and the pioneering photographer Julia Margaret Cameron lived in Freshwater Bay, where Edmund Lear and Lewis Carroll were regular visitors. But the main reason the isle holds such enduring fascination is, of course, thanks to Queen Victoria. She and Albert loved Osborne House, and you’ll be seeing more of their summer palace soon as much of the upcoming film, Victoria & Abdul, starring Judi Dench, about the monarch’s friendship with her Indian servant Abdul Karim, was filmed there. Then we’ll get another look when the second series of ITV’s Victoria arrives on our screens this autumn.

Royal retreat: Queen Victoria’s Osborne House. Isle of Wight.

Royal retreat … Queen Victoria’s Osborne House. Photograph: Oli Scarff/Getty Images

After the Needles we turned east, past Yarmouth’s pretty harbour, before snaking along the Hamstead Heritage coast. It’s all tiny inlets and creeks, wooden bridges and fields of singing grass. Across the glinting Solent we see white sails and Lymington in the distance. Late in the afternoon we jogged round the northerly Gurnard Point and into Cowes, where we stopped for the night. This is where the event becomes a little surreal. Though we were running this race, the majority of our fellow entrants were hikers. Endurance walking is a growing area for “weekend challengers” and they hoped to circle the island in one shot, going through the night. Like hares and tortoises, most would beat us, but by the end they were like zombies, stumbling towards the finish line, their unblinking eyes fixed on the horizon as they stumbled ever onwards.

They also miss out on a night out in Cowes. Straddling the Medina river, the harbour town is the yachty heart of the place and has a buzzy, holiday feel all year, though Cowes Week – the world’s oldest regular regatta – is clearly when they really let rip. Breton jerseys, tanned legs and sea-worn deck shoes are mandatory. We opted to camp, so we headed up the hill to our tent. We sneaked into the local cricket club to take advantage of subsidised beer and polish off a curry. How many other races include a camping, beer and curry stage?

Sailing during Cowes Week on the Solent

Big blue … sailing during Cowes Week on the Solent. Photograph: Alamy

Day two began early. We heard that 300 competitors had abandoned with blisters and fatigue. It turned out the bulk of them were men – women are made of sterner stuff. We started by catching a ferry across the Medina, floating under the huge steel arms of old shipping cranes. We skimmed round Osborne House, and peered over the walls of the Abbey of Our Lady of Quarr, a monastery that is still home to a group of Benedictine monks. Then we ran through Ryde. It has the oldest and second longest pleasure pier in the country. The words faded and glory spring to mind, as they often do on the Isle of Wight. Bembridge followed, then miserable Sandown and the exhausted hulk of Shanklin lying like a beached whale at the south-east corner. It started to rain. The sea looked fierce. But Ventnor was nicer – Winston Churchill used to holiday here as a boy, and Karl Marx once spent the summer. How strange.

The final 10 miles took us around the bottom of the island, past St Catherine’s Point. This was the wildest and most remote section, the cliffs towering and dramatic. Late on Sunday afternoon we arrived back where we began. We were delighted. We’d gone all the way round – and not one of us had been seasick.

Way to go

Ultra Challenge organises a series of charity walking and running events around the world. To enter the Isle of Wight Challenge 2018, go to Entries start from £60. For more information on the Isle of Wight, go to

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