Goodbye to plodding along in the slow lane, hello Harley-Davidson and the open road!

The smell, the bugs, the wind on your face! Park the car, overcome the fear and saddle up with TV presenter Henry Cole as he rides Route 66 - and feel what it’s like to unbelt yourself from the boring everyday…

‘Few experiences encapsulate the essence of freedom quite like motorcycling’ ( Henry Cole)

The night before I go on any great motorcycle journey, I get the fear. Checking my will is up to date and all that. Then with Route 66, I am thinking: Oh my God, I’m going to be riding in Chicago! Oh my God, that is terrifying!

Day of departure, I have a total crisis of confidence. I think, Do you know what? I’d rather be in bed now. Sod this trip. The Harley dealership where I tend to pick up my easy rider is on the east side of Chicago, so I get up, get the bike and go. That’s my suggestion: get out of Dodge. Because once you’ve got out of Dodge, you’re going to feel a great pressure off you.

For the first 210 stretch to Springfield, you want to try to leave Chicago through Joliet (where the Blues Brothers were from) and just get yourself out of town. It’s a little bit sketchy in the hinterland of Chicago, but very quickly you’ll find the urban stuff drops away. Keep riding out of Chicago and just don’t stop until you have a good 70 or 80 miles under your belt. Then you’ll begin to settle into your journey and start to think: Yeah, OK, this is going to be amazing, actually.

The next day, you’ll wake up for your first motel breakfast. Your motorbike is outside your room. You sit on a plastic chair on the balcony and drink the most delicious, terrible coffee you’ll ever drink. But... you’re free, you know? You’re on Route 66.

The thing about being on a motorbike – and this is a good thing as well as a bad thing – is that any place you go, you don’t see the usual things tourists see (which in Springfield means superficial Abraham Lincoln stuff – he is the town’s second-most famous resident, after Bart) and colonial town squares.

I mean I’ve done great drives in cars, but you don’t really meet anyone. I am an absolute believer in the supremacy of the motorcycle if you want a road trip to be a meaningful experience. A motorcycle is not just a mode of transportation; it’s an extension of yourself. It offers an unfiltered connection to the road, the cold wind, the scorching heat, the smell of the rain coming in and even the bugs in your face. It’s an experience that transcends words. You have to live it to understand it.

The allure of vulnerability on a motorcycle is irresistible. It’s about facing the unknown on a desolate road. To truly find yourself, a bit of danger is necessary – a willingness to step out of your comfort zone. On a motorcycle, you’re not attending to your wants; you’re just addressing your needs: fuel, warmth, safety and spiritual peace.

A Route 66 motel in Barstow – a must for the real deal (Henry Cole)

In the vast, sprawling tapestry of life, where the mundane often intertwines with the extraordinary, few experiences encapsulate the essence of freedom quite like motorcycling. It’s a pursuit that offers an escape from the relentless monotony of daily obligations – the suffocating embrace of mortgages and bills and the brain-melting tedium of responsibilities that we, as functioning adults, find ourselves shackled to. You can feel like you’re on a hamster wheel of doom, man. But the moment you swing a leg over a motorcycle, you’re no longer just someone who exists within the confines of a structured society.

You become an explorer, a rebel, a wanderer on the vast canvas of the earth. You are a lone rider, astride a gleaming machine, and with the road stretching endlessly ahead, you experience a profound sense of autonomy – a feeling very much at odds with the structured, often predictable paths we are all nudged down in our lives.

Motorcycling is not merely a mode of transport; it’s a journey into the soul of freedom. The roar of the engine, the rush of the wind, the rhythmic dance of the machine gliding over tarmac – all these sound, to me, like a symphony of liberation. Out on the open road, the petty concerns of daily life disappear in the rear-view mirror. All those day-to-day obligations fade away to be replaced by the immediacy of the journey and the road ahead.

‘The allure of vulnerability on a motorcycle is irresistible. It’s about facing the unknown on a desolate road’ (Henry Cole)

But this freedom is not just about the physical act of riding. It’s a mental, almost spiritual state. On a motorcycle, you’re exposed – vulnerable yet invigorated. Biking isn’t just about getting from A to B; it’s about the experiences between those points, the moments of introspection, the unscripted interactions and the raw beauty of the world as experienced on two wheels.

Moreover, in a world where status is often measured by material possessions and job titles, a motorcycle is a powerful equaliser. It strips away layers of expectations, allowing individuals to connect on a more authentic level. Biking culture thrives on this sense of community and shared passion.

Being open to this camaraderie is fundamental to the motorcycle touring experience. I believe it’s about recognising that every rider you meet is a potential friend, a kindred spirit on the same quest for freedom and adventure. This openness can turn a solitary trip into a collective narrative, weaving your thread into the larger tapestry of motorcycle culture.

For me, it is that essence that lies in the Harley-Davidson and the road stretching out from Chicago. Is it a road to spiritual freedom? The answer lies within you as an individual.

‘In this world, you’re no longer boxed in by the confines of an aisle or a schedule’ (Henry Cole)

Route 66 is a bit loose in places. For much of the ride out of Chicago, it runs alongside Route 55 and disappears in bits, but don’t worry too much about that. The original 1926 alignment goes directly through Springfield, and you’ll start seeing the signs pop up again as you get closer.

Route 66 was built to give desperate people a second chance, a chance to make a success out of the failure that was going on around them.

As the Boulevard of Dreams unfurls between Chicago and Springfield, you begin to realise that, spiritually, you are now actually becoming an integral part of the American Dream – an adventurer, leaving behind the confines of your own world, and heading west into the unknown; an alien on an American machine, retracing the steps of those who came before you.

Route 66 is a pressure cooker, releasing acceptance and understanding. It’s not merely a ride; it’s a slow evolution of identity. You’re no longer an observer on the outside looking in; you’re a participant. You are it. And that is a slow development which probably doesn’t fully manifest itself until you get to LA. So, that’s why I think you should do the whole trip. Right? Because yes, the destination is important, but it’s the journey itself that transforms you.

Flexibility in my schedule isn’t just about spending time in Springfield; it’s about spending time with myself. This journey is an opportunity to do something for me, to embrace the raw emotions of fear and vulnerability.

We are lucky enough not to be being driven off our homes by the Dust Bowl and rapacious landlords, but the resurgence of interest in riding Route 66 – a road with boundless possibilities – reveals a deep yearning to reconnect with simpler times and classic experiences, especially in times of uncertainty and change.

The presenter resting up near Gallup, a city in New Mexico (Henry Cole)

When you ride a Harley (which, in my view, is a need) and you ride it alone in America, you’ve got to make the adventure happen. You’ve got to go into a diner on your own, order a burger and talk to people. There’s no one with you. No – you have to make conversation and make your own luck.

So, consider this journey as the opening act of your very own movie. Act one is all about setting the scene, introducing characters and embarking on the adventure. When you leave Chicago on your Harley, you can physically feel the stress and pressure of getting the journey started lifting.

The very act of riding – the rhythmic hum of the engine, the feel of wind against your body, the ballet of manoeuvring through landscapes – serves as a meditative process. It’s a way to reconnect with yourself, to find solace in solitude or companionship in the shared silence of fellow riders. Each turn offers a new perspective; each stop a moment to reflect and breathe.

In this world, you’re no longer boxed in by the confines of an aisle or a schedule. You’re not a passive observer but an active participant. A part of the environment. And the challenges of the road – the changing weather, the varying terrain – become not sources of stress, but opportunities for exhilaration and growth.

It’s a declaration of independence from the constraints of conventional travel – a way to reclaim autonomy and find peace amid the chaos. And once you have swung your leg over the motorcycle and departed Chicago, every mile becomes a release.

The fear drops away, and that first night, as you sit outside on the aforementioned crappy plastic chair with your feet on the bike, and think: Wow, man – I’m starring in my own American movie; holy smoke... this is gonna be OK, you might find yourself chuckling with delight at your own good luck.

Henry Cole’s ‘Riding Route 66’, published by Quercus, is available here

‘Riding Route 66’ follows Henry Cole as he travels the ‘mother road’, one of the most famous roads in the USA, on a journey of self-discovery. Crossing the width of the country, an immensely challenging road to travel. Henry has ridden it three times.