I challenged a professional hitchhiker to a race around the Isle of Wight. Who won?

Simon Calder

Since April this year, Trevor Daneliuk, aged 24, from Vancouver Island in British Columbia, has been live-streaming his life on the road on the global platform Twitch.

“From when I’m in my tent in the morning to when I go to bed at night, the camera is on and you get to see the whole process, as it happens,” he says.

“I started hitchhiking because I didn’t like the Greyhound bus. I did four years of hitching and had 700 rides in 25 countries before I decided to do live-streaming.

“I wanted to show people what hitchhiking is actually like unfiltered, unedited. So I started livestreaming the actual process.”

While Trevor digi-hitches his way around the world, I thumb in a more analogue fashion simply to get to places I need to be. And I wanted to see how we measured up.

Why the Isle of Wight?

The destination for the hitch race: the Isle of Wight (Google Maps)

Hitchhiking races from A to B are flawed because competitors can get in each other’s way. On a circular route, which the Isle of Wight provides, one contestant can go clockwise and the other anticlockwise. And with a total driving distance of about 55 miles and no motorways, it is a manageable project for a wet and windy day in December.

Because the towns on the island are not exactly giant conurbations, there is no need to get tangled up with endless suburbs, which have been the death of many a travel dream.

Beginning and ending in the port with ferry and hovercraft links from Portsmouth also provides some scope for Ryde/ride puns.

The hitchhikers: Trevor Daneliuk and Simon Calder (Simon Calder)

The rules

Trevor goes anticlockwise around the island, I go clockwise. We each have to take selfie in front of two “checkpoints”: St Catherine’s Lighthouse, marking the deep south of the Isle of Wight, and the Red Lion pub in Freshwater in the west of the island.

No public transport or taxis, obviously. Trevor had an additional rule, which was that no one who was watching his livestream could come out and pick him up.

The race begins on Saturday 1 December from the Blaze cafe on the Esplanade in Ryde.

Breakfast with Trevor Daneliuk (Simon Calder)

10.45am: Ryde, Esplanade

“I have a lot to prove,” says Trevor as we part. “If I don’t win, I look bad, because I’m the professional hitchhiker. But if you lose, you lost to the professional hitchhiker.

“Lots riding on the line for me. My pride, mostly.”

The rain is incessant.

10.46am: Ryde, heading east

I cross the road to aim east along the seafront, past the bus station and the hoverport, and start hitching immediately. But much of the traffic is local, and – unlike Trevor – I have opted not to create destination signs. On a relatively small island, they can make a hitchhiker look too professional. Which I guess is Trevor’s look. He also has a serious backpack, and his live-streaming kit – a camera and microphone on a stick.

10.49am: Ryde, heading west

Trevor tells the people watching: “He’s using a paper map.” Then adds: “He probably has access to proper maps.”

10.55am: southeast outskirts of Ryde

“I can take you to Tesco!” Vicky, who’s driving, and Felix, who’s five months old and asleep, stop in their yellow Fiat. As that is the best offer I have had all day, I gladly accept.

Vicky says that France is the best place for hitching, especially if you are travelling with a small dog.

10.56am: western outskirts of Ryde

Trevor is by the road with his sign reading “Newport,” the administrative centre of the island. He gets a lift to Wootton, three miles along the road.

Before he gets into a car, Trevor tells drivers who stop that he is making a live video documentary about hitchhiking, and asks: “Is that something you are comfortable having in the car with you?”

He says: “95 per cent of people are 100 per cent OK with that,” and turns down lifts when someone doesn’t want the camera.

11.09am: the Tesco roundabout outside Ryde

Seven minutes after Vicky drops me off, Cathy and Yvonne stop.

Cathy says I am the first hitch-hiker she has ever picked up. “You’re not an axe-murderer,” she says, “you’re the man off the telly.” I wonder if I should advise her not to pick up people who appear as suspects on Crimewatch, but instead reflect on how it is impossible to know how many motorists drive straight past because they have seen me on TV, but I imagine they cancel each other out.

Fourteen minutes later, the pair drop me in Shanklin.

11.23am: A3054, heading west

Trevor is now in a car driven by Annie. The live-streaming has been intermittent, due to poor mobile coverage in parts of the Isle of Wight. But I sense he is happy, because he told me earlier. “I love that feeling of just hopping in cars all day, getting to a place you’ve never been before, as the sun sets.”

Five minutes later, he is dropped off. It is still raining.

11.25am: A3055, heading south

Dale (the driver), Stuart, Gary and Nick are from Bromley in southeast London, and in a fortunately large SUV. They are not lost, but on the island to visit a friend. They would like to be hiking but, given the atrocious weather, they are going for drive – aiming all the way along the south coast to the far west, which would suit me fine, except for that pesky St Catherine’s checkpoint.

Simon in the rain outside the first ‘checkpoint’ – St Catherine’s Lighthouse (Simon Calder)

It is a long walk down to the lighthouse, enlivened by passing the Enchanted Manor – “A perfect paradise for special occasions”.

The Isle of Wight’s not at all creepy Enchanted Manor (Simon Calder)

11.43am: western outskirts of Newport

“You have a friendly face,” says Leanne, as she welcomes Trevor, his backpack and his camera gear into her car.

He told me earlier: “My goal when presenting myself is to look as clean and un-scary as possible. People are intimidated, they’re scared of hitchhikers in general, and my goal is to look like someone you’d want to pick up, like someone you’d want to hang out with.

“So I try to keep clean-shaven, I try to have my hair looking fairly presentable, not super-long and shaggy. I try to have clean-looking clothes, I try to look like I don’t smell.”

When Leanne apologises for the scruffy interior of her car, Trevor says: “I usually sleep in a tent in the woods, so this is luxury.”

As she drops him off outside the Red Lion at 12.03pm, Trevor says: “I don’t think he could have beaten me here.” He’s right; I have visited St Catherine’s Lighthouse and am presently walking in the rain back up to the road, about 15 miles from the pub.

Simon outside the Red Lion pub, the second ‘checkpoint’ in the hitch race (Simon Calder)

12.06pm: Niton, the village above St Catherine’s Point

Anoushka winds down her window and enquires kindly: “Are you alright?” She is the front passenger seat. Stratford is at the wheel. Sam has to share the back seat with me. They, too, are Londoners visiting friends on the Isle of Wight.

Stratford drives expertly through the murk as I learn the secret of Sam’s professional success in multilingual recruitment: “Be honest and trust people.”

They are bravely going for a walk along the shore from Compton Bay. In the car park, they kindly take a selfie with me, and their friends in another car.

A selfie by Compton Bay (Simon Calder)

12.08pm: Red Lion, Freshwater

So confident is Trevor of victory at this stage that he goes one better than simply grabbing a selfie at the Red Lion – he orders, and swiftly downs, a pint of beer.

12.32pm: Compton Bay car park

In heavy rain, motorists take one of two different attitudes to hitchhikers. Either: “He’s soaking – I’m not letting him in my nice, warm and dry car.” Or: “He’s soaking – better pick him up”.

Fortunately Anita, Jim and Beryl are in the latter camp. They take me past the site of the 1970 Pop Festival (featuring Jimi Hendrix, Leonard Cohen and The Who) to the Red Lion (featuring Love, Joy and Merry Christmas on heart signs in the window), where I thank them and get out at 12.41pm. I have no time for a drink because …

12.41pm: heading southeast along the A3055

“You’re going to take me to the lighthouse?”

Trevor is in a large, elderly minibus belonging to an evidently friendly and helpful driver, Sean. Trevor confirms to Sean, and to his live-streaming viewers, that the vehicle will detour down to the lighthouse.

From what Trevor told me earlier, Sean is in the top demographic for lift-giving motorists.

“The most common would be single men on the older side of things. People who used to hitchhike or at least used to see hitchhikers. It’s in their memory that it is an actual thing that happens. Whereas the younger generation has never seen it before and it’s more like an entertainment or curiosity thing to see a hitchhiker. There’s no thought to pick you up. It’s more like, ‘Wow, there’s someone hitchhiking’.”

As Sean learns about Trevor’s professional status, he says: “You’ve probably met everyone in the world, then.”

12.51pm: walking north out of Freshwater

After Dylan and Katie pick me up, I don’t have long to get to know them, because they drop me less than a mile further along the road, at Norton Green. (Not because of personal hygiene issues, just because that is where they live.)

But barely have I stuck out my thumb than Heath arrives (he’s a splendid driver, not a geographical feature). He is going to Cowes, well north of the most direct route to Ryde, but a good rule in hitching is to accept a long lift even if it involves a bit of a detour. In the context of the Isle of Wight, this 15-mile journey is a long way.

Heath tells me of his remarkable commute from his home in the far west of the Isle of Wight to Cowes by car, where he boards the ferry to Southampton. On the mainland, his second vehicle is waiting, and he drives down the coast to his office in Fareham.

I can see clearly now the rain has gone. The island looks adorable, with the last leaves of autumn bestowing flecks of gold on a picture of rural serenity. He drops me off at the Floating Bridge at 1.17pm.

1.17pm: A3056/A3054 junction in Newport

Trevor is just four miles south and already on course for Ryde. Sean laid on the Tour de Lighthouse and then drove Trevor north to Newport, his original destination. That means Trevor will end up doubling back along the A3054, but there is no rule against it.

The young Canadian is a charmer, and Sean offers to make a second diversion and deliver Trevor to Ryde.

1.18pm: Floating Bridge, Cowes

Well, this is awkward. The “Floating Bridge” across the River Medina isn’t a bridge at all, but a chain ferry. And unlike some river crossings, it isn’t free. So I am faced with hitching all the way south to Newport, or breaking the “no public transport” rule. I pay the £1.50 fare (yes, for a 200-yard, two-minute journey – a higher price-per-mile than Concorde). By the time we cross the mighty Medina, it is 1.27pm. On the far side I scamper off the (presumably gold-plated) ferry and take up position to hitch the cars leaving the “bridge”.

Tim, in a sleek black Mercedes, stops and says he is heading for Ryde.

Simon at Cowes Floating Bridge (Simon Calder)

1.33pm: Ryde, Esplanade

Sean drops off Trevor, with a farewell message: “Be safe and be lucky.”

As I listen to Tim’s outlook on life, while being chauffeur driven in a Merc through glorious countryside, I am feeling fortunate, too.

Tim drops me outside the cafe at 1.50pm. Trevor is drinking tea and captures my arrival on camera.

“We both got lucky, and I got a little more lucky,” he says.

“At some point, my body and my mind will be tired, but for now there’s no other way I’d like to travel.”