
John Ferguson, who, with his distinctive white beard, can often be seen cycling on local roads as he leads a tour group or commutes from his West Bay home, recently completed the ride of his life.
Ferguson was one of more than 25,000 cyclists from 17 countries who covered 424 miles over six days across the US state of Iowa last month in the annual RAGBRAI ride.
“I don’t know why I waited until I was 65 years old to do this bike ride, because it was absolutely magic,” he told the Compass.
During the epic cycle, he rode for six to seven hours a day and, throughout the entire ride, covered 18,000 feet of elevation.
“They say Iowa is flat, but I call BS on that,” Ferguson said, as he recalled the many uphill trails RAGBRAI took him on. “My legs felt it every single day.”
On one stretch of road, he said, he rode for over a mile on a 12% gradient – “That’s like riding over the Kimpton bridge, but imagine it being twice as steep and a mile long.”

Seven months of training
Living on an island that really is flat, it’s not easy to find somewhere to train for such inclines. Ferguson says the only way to prepare for that in Grand Cayman is to cycle into a headwind along the East End Queens Highway loop.
He started training for RAGBRAI in January this year, covering more 3,000 miles before boarding the plane to Iowa last month.
“All the training still did not prepare me for those climbs that never ended. You just keep going up and down,” he said, adding that he’d sometimes find himself cycling downhill at a speed of 42 miles per hour, followed immediately by a steep hill where he could only hit speeds of 4 mph.
For five days after he returning home to Cayman from Iowa, he gave his tired legs a rest, travelling by four wheels rather than two, but got back on his bike on Friday, 2 Aug., to cycle into George Town for a watch party at Constitution Hall to support Cayman’s own Jordan Crooks in his 50-metre Olympic swim final.

On four of the six days of RAGBRAI, he went off-road, riding on gravel trails that were rougher and much bumpier than the asphalt roads.
RAGBRAI was started in 1973 by the Des Moines Register newspaper in Iowa, and is an acronym for the Register’s Annual Great Bicycle Ride Across Iowa. It is now the world’s oldest and longest multi-day cycling event.
This year’s ride started in Glenwood, by the Missouri River, and ended in Burlington, beside the Mississippi. RAGBRAI riders have a tradition of dipping their back wheel in the Missouri at the start and their front wheel in the Mississippi at the end – which Ferguson said he was delighted to do.
He posted on social media a photo of himself looking positively ecstatic as his front wheel sat soaking in the Mississippi at the end of the gruelling event.

‘RAGBRAI magic’
“It was the most amazing experience I’ve had since, I can’t remember when,” Ferguson says of RAGBRAI. “I’ve made some friends now that it seems like I have known them my whole life.
“I can’t really explain how magic RAGBRAI really is.”
‘RAGBRAI magic’ is a phrase riders often hear, he explained, as he recounted a story that he says epitomises those words.
Ferguson, who every year appears during Cayman’s Pirates Week festival as the pirate ‘Dry Rot’, said on the evening before the ride began, he was cycling to his camping ground in Glenwood when he heard someone shouting “Dry Rot! Dry Rot!”
“I was looking around on my bike and thinking, ‘I’m in Iowa. Nobody in Iowa knows my pirate name is Dry Rot.’ It was the weirdest thing. Well, up the road, I see this guy on a bike riding towards me, waving his hand and calling out ‘Dry Rot’.”
It was a friend he’d met while cycling along the north coast of Jamaica in 2015, and whom he hadn’t seen since.
“There were tears,” Ferguson said, as he recalled the reunion on the roadside.

During the cross-Iowa ride, Ferguson was on a 210-strong team, but with thousands taking part in the event, he often didn’t see those teammates until he’d arrived at the town at the end of a day’s ride, where they all pitched their tents on specially designated campsites.
One of the towns they rode through was Greenfield, which suffered major damage in a devastating tornado in May. It was that town’s Hurricane Ivan, Ferguson said.
The organisers had asked the town officials if the ride should bypass Greenfield this year, but they said they wanted the cyclists to come through. “That day, more than $55,000 in cash was spent by the bicyclists,” Ferguson said.
“I emptied my wallet”, as did many others, he added.
In the small towns the riders passed through, there was plenty of support from the locals. “There’d be girl scouts selling lemonade and church ladies passing out apple, rhubarb and blueberry pie slices,” Ferguson said.
After a hard day’s riding, the cyclists were treated to evenings of live music from local rock bands, as well as BBQs and beer tents, before bedding down for the night in the tents and sleeping bags that were transported from town to town by support crews.
Ferguson, who works at Paddle Wheel Adventures and leads cycle tours on island, says he’s already signed up for next year’s ride, and hopes to organise a team from Cayman to accompany him.
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