Biking Along Britain’s Remaining Roman Roads

Some cyclists yearn for races and organized rides, but Guy Stapleford fell back in love with biking on a 2,000-year-old route

January 31, 2025 11:56 am EST
Guy Stapleford emerges from from the trees on a shady trail. Sketches of Roman columns in the corners of the photo.
This road — straight as it gets — was built by invading Romans 2,000 years ago.
Phil Hill

British cyclist Guy Stapleford never considered himself an athlete. Instead, fitness came to him as a form of salvation.

Flashback to 2016: Stapleford was newly divorced and not long clear of a bout of pancreatitis brought on by alcohol abuse. Alone in a new flat, he realized he was teetering on the edge of another rabbit hole of drinking and depression. In other words, it was a point in his life where something had to change. And it did.

“I bought some trainers and just started running,” Stapleford, now 42, tells InsideHook via phone from his home in the U.K.

Prior to this, he’d enjoyed the odd kick-about — “dads’ football” is how he words it. But nothing major. He was soon knocking out 5Ks, and eyeing up his first half marathon, when he started hearing a lot of positive chatter about cycling. One $122 eBay bike later, and Stapleford’s 2017 became subsumed by it.

“I did one new thing every month, over the course of the whole year,” he says of his early biking days. “At the end of November, I rode solo from John O’Groats in Scotland to Land’s End in Cornwall over the course of nine days.”

Stapleford on his bike passing through an ornate tunnel.
“[For me], biking stills the mind and quiets the inner voice,” Stapleford says. “It’s a really powerful thing.”
Phil Hill

Has Anyone Cycled This Before?

After this first big adventure, Stapleford had the long-distance bug and set his sights on the Race Across America, a 3,000-mile odyssey from California to Maryland.

He finally spot secured a spot in June 2022. Then everything went sideways. Stomach trouble sank his chances and he was forced to bow out. Back home, his new partner gave birth, meaning he was busier than ever, while a hernia kept him off the saddle indefinitely, necessitating surgery.

After three months off the bike, he gradually began building his fitness back. This wasn’t idle time. Getting out every weekend and smashing miles on the bike had begun to feel like work, so while he was recuperating, Stapleford began to plan a new challenge. 

He got hold of a gravel bike and began looking for trails to tackle. A famous photo of the Halnaker Tree Tunnel — a bucolic trail with trees arching over from either side of the path to form a living tunnel — was just the thing to get his mind whirring. When he heard the tunnel was part of Stane Street, an old Roman road, his mind was made up.

“I’d never heard of Stane Street, despite being an archeologist by qualification,” he laughs. “The history piqued my interest and I wondered if anyone had cycled it before. How much is still there? How much can I actually ride?”

Four images, featuring Stapleford pushing his bike through an old square, a profile photo while wearing his bike helmet, signage for the Roman roads, and his bike cleats against the grass.
Stapleford couldn’t find a record of a cyclist ever riding the 62-mile Roman road that carves south from London.
Phil Hill

Surviving Down the Centuries

A quick history lesson here, one that isn’t covered in Gladiator II. When the Romans invaded Britain around 43 AD, they found a lot to like. Sadly, the infrastructure wasn’t doing it for them. Nor were the belligerent locals. So the Romans did what they do best, building long, straight roads over the country, primarily so they could move their troops about at rapid pace. Bad news for the native Britons, good news for the Romans, who stayed in the country for almost four centuries. 

In total, around 2,000 miles were built. Today, most of these roads have faded into history, lost beneath grass or tarmac, but Stane Street, connecting central London to Chichester 62 miles to the southwest of the capital, survived. 

Better still, a map was available via Britain’s Ordnance Survey, an open-access database mapping the country’s bridle paths, footways, ancient roads, et al. For Stapleford, it seemed like the perfect adventure, especially as he couldn’t find a record of anyone ever having cycled it.

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Riding Roman Roads

A few months’ planning later and he was ready to go. “You start in Borough Market, right by London Bridge Tube stop, and close to the Tate Modern gallery,” Stapleford says. “It’s one of my favorite places in London.” But, like most major cities, London isn’t perfectly picturesque.

“The next 25 to 50 miles coming out of London into the county of Surrey was not particularly fun or inspiring,” he laughs.

Out in the Surrey Hills, however, the scenery began to change. There’s a reason many of Britain’s top footballers decide to move out to Surrey, after all. “That was when I started to realize, I’m on a Roman road here,” says Stapleford. “It was dead straight.” Which isn’t to say, easy.

“There were some really unexpected bits, like we had two sections where I had to get completely off the bike,” he says. “One was this footpath that was so overgrown with nettles and thistles and brambles that you couldn’t ride a bike down it. Another was one bit where a tree had fallen over across the path — an entire, complete tree — so I had to throw the bike over the top of it and then climb under the tree. It was mad.”

Mercifully, he wouldn’t have to contend with enthusiastic British vegetation for long. He bashed the entire ride out in five hours and six minutes.

“Right at the end there was this horrible, gravelly hill with a marker denoting the Roman road at the top,” he says. “It was pretty cool, but also absolutely horrible and I was completely not fit enough for it. But you could see the road going downhill from there and it was the best bit of the whole ride for me.”

From there, it was downhill, past a windmill, into the famous Halnaker Tree Tunnel and out into the city of Chichester near Britain’s south coast, finishing at the city’s cathedral. 

“It’s a stunning city,” says Stapleford. “To go from the natural beauty of that green lane into the manmade beauty of the cathedral is quite a nice little transition.”

Guy Stapleford rides his bike on a country lane. Light sketches of Roman columns adorn the photo.
Stapleford credits the Stane Street ride with renewing his love of cycling.
Phil Hill

“A Bike Is an Amazing Thing”

While the ride wasn’t overly taxing for a cyclist of Stapleford’s ability, he says it was the sort of route that you wish could’ve continued on and on. And while that one-day adventure may be long done (Stapleford completed the effort in late September 2023), its impact on him and his riding lives on.

“It just sparked the want to enjoy life, and do something different,” he says. “I’ve never been one to follow the crowd; I don’t do a lot of racing or organized events because I feel like I want to do something different, and the beauty of all of this is telling the story, inspiring people to go and either do the same thing or find their own adventures.”

The Race Across America might finally be on the cards in the next year or two, but it was Stane Street, a 2,000-year-old Roman road, that helped Stapleford fall back in love with cycling again. 

“A bike is an amazing thing for me,” he says. “It’s got me through the hardest time of my life. When you go through that trauma of your marriage breaking down, to have that thing that can still the mind and quiet the inner voice is a really powerful thing. It made me realize I had no purpose before. Family is everything, but you’ve got to have something for you, wherever your situation, and I didn’t have anything. Now I feel like I’ve got a much richer, fuller life because of the bike.”

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