Chapter 2 — A Cavalry Charge
With the track rated Soft 5, the field assembled for the 2000-metre feature, and the Port Macquarie Cup was underway.
Bear On The Loose was always going to be an important part of the tactical picture, while Cavalry Man had arrived with the credentials of a horse capable of sustaining a serious effort over the distance.
As the race developed, the contest became a test of staying power and determination. Cavalry Man produced the sustained run that Terry had noticed watching the replay, carrying his effort through to the finish rather than relying on one fleeting burst of acceleration.
Under Jace McMurray, he prevailed to claim the 2026 Port Macquarie Cup for trainer Lindsay Gough, adding another significant victory to an already impressive preparation.
Bear On The Loose finished second for Gai Waterhouse and Adrian Bott, while Chris Waller’s Unlimited took third ahead of stablemate Medatsu.
For Cavalry Man, the result confirmed that his Toowoomba Cup success was no isolated performance. Different racecourse, different opposition, another Cup to take home.
And for McMurray, it was a winning ride on an afternoon when the horse beneath him answered the challenge.
Chapter 3 — Old Friends and New Memories
There was another familiar name among the runners, one that regular Race Day Co readers might recognise.
King Jerry.
We had followed him previously at Rosehill, and here he was again, this time taking his place in a Country Cup. He was prominent during the running but couldn’t sustain his effort through the finish, eventually coming home eighth, 3.57 lengths behind Cavalry Man.
Not quite the afternoon his connections would have hoped for, but King Jerry remains part of our growing racing notebook. There may yet be another chapter in his story.
For Lucy and Sophie, the afternoon brought their Port Macquarie assignment to a satisfying conclusion. They had discovered a town with a remarkable past, explored its racing heritage, enjoyed a memorable evening together and watched a worthy Cup winner add another trophy to his collection.
As they prepared to leave the course, Lucy’s phone buzzed.
A message from Tommy.
“Good work, girls. Hope you enjoyed Port. Boys want to know whether you managed to get out for dinner.”
Sophie read the message over Lucy’s shoulder.
“Dinner?” she said innocently. “Well, we certainly had something to drink.”
Lucy laughed.
“Do you think Tommy knows?”
Sophie slipped her sunglasses back on.
“Darling, I suspect Tommy knows considerably more than he lets on.”
And somewhere back at Race Day Co headquarters, Ben and Jack were probably still wondering.
The girls had completed their assignment, Cavalry Man had won the Cup, and Port Macquarie had given us another chapter worth remembering.
From the waterfront to the winning post, Port had delivered.
Part 1 - Where the River Meets the Sea
There are places that announce themselves before you have properly arrived, and Port Macquarie is one of them.
For Lucy and Sophie, the first impression wasn’t one particular building or landmark. It was the light. Morning sun across the Hastings River, boats sitting quietly at their moorings and, not far beyond, the Pacific rolling towards a coastline that has been drawing visitors here for generations.
Sophie had already decided where breakfast should be. Lucy, rather less interested in breakfast and rather more interested in exploring, had other ideas.
They compromised, which generally meant coffee first and Lucy getting her way afterwards.
There was something else rather appealing about this particular Race Day Co assignment. For once, it was just the two of them. No men offering directions, studying form guides over breakfast or announcing that they knew a quicker way to the racecourse.
“A girls’ trip,” Sophie had declared somewhere along the highway.
Lucy preferred “assignment”, although she wasn’t entirely convincing.
They had a few days in Port Macquarie, a Cup meeting at the end of it and, unless Race Day Co had quietly introduced a curfew nobody had mentioned, perhaps an evening or two to investigate whether the town became quite as respectable after sunset as it appeared over morning coffee.
There would be time for that.
For now, Port Macquarie was waking up around them.
You don’t have to travel very far to find it.
You simply have to walk uphill.
The View from Church Hill
At the top of Hay Street, on ground that has watched Port Macquarie change for two centuries, stands St Thomas’ Anglican Church.
It isn’t a grand building in the manner of the great cathedrals. Perhaps that is part of its charm. Its importance reveals itself slowly, because St Thomas’ belongs to a very different Port Macquarie from the one Lucy and Sophie had left beside the river only a short time earlier.
The settlement was established in 1821 as a place of secondary punishment for convicts. Church Hill became one of its important sites, and the buildings that remain there provide an extraordinary physical connection to those first years. The old dispensary dates from 1822, the former surgeon’s residence from 1822–23, and the foundation stone of St Thomas’ was laid in December 1824. The church itself was built by convict labour under military supervision, with its first service held in February 1828.
Lucy stopped for a moment.
It is one thing to read that something is two hundred years old. It is another to stand beside it and realise that the town below has effectively grown up around it.
Those early years were not the beginning of Port Macquarie’s story, of course. Aboriginal people had lived in this country for countless generations before Europeans arrived. But the colonial settlement that eventually became the modern town began here in circumstances far removed from today’s relaxed coastal destination.
By 1830 Port Macquarie was opened to free settlement. The town was resurveyed, its population grew and roads, churches, schools, farms and businesses gradually pushed the settlement beyond its penal beginnings.
Two centuries later, St Thomas’ remains in use.
Perhaps that is the detail that says most.
Buildings survive for all sorts of reasons, sometimes through preservation and sometimes through good fortune. This one never became merely a relic behind a rope. Generations continued to walk through its doors while Port Macquarie changed outside them.
Sophie looked back down towards the modern town.
Somewhere between Church Hill and the Hastings River below was the story they had come looking for: not everything about Port Macquarie, because no town worth knowing can be disposed of in a few paragraphs, but one small window into where it came from.
Next time, there would be another story.
Then Came the Horses
It didn’t take horses quite as long to find Port Macquarie.
The Port Macquarie Race Club traces the district’s racing story to 1845, when local enthusiasts gathered to watch horses race on sand tracks near the Hastings River. More than 180 years later, racing remains part of the social life of the district, although the surroundings have changed considerably.
Today’s racecourse on the Oxley Highway hosts more than twenty meetings a year, but one sits apart.
The Port Macquarie Cup.
On Friday, 9 October, the town will dress for it again. The 2026 Cup meeting brings together the things country racing does particularly well: serious racing on the track, fashion and hospitality around it, old racing friendships renewed and plenty of people who might only attend one meeting all year but wouldn’t dream of missing Cup Day
And there is considerably more than local pride riding on the feature itself.
The Port Macquarie Cup is run over 2000 metres and carries automatic qualification for The Big Dance at Randwick, placing this coastal meeting firmly on the road that Race Day Co has been following through country New South Wales.
For Lucy and Sophie, that could wait.
There would be acceptances to study, barriers to consider and a Cup field to pull apart soon enough. That belongs to another day, and another part of this story.
For now, they had seen two Port Macquaries.
One beside the water, bright and modern, looking out towards the Pacific.
The other waiting quietly on a hill above it, still carrying the fingerprints of a town more than two centuries in the making.
And somewhere between the two, horses had been racing since 1845.
Friday couldn’t come quickly enough.
PORT MACQUARIE CUP 2026
Part 2 - Cup Eve, and Strictly Business
By Thursday evening, Lucy and Sophie had fulfilled most of the obligations expected of two responsible Race Day Co representatives on assignment in Port Macquarie.
They had explored the town, climbed Church Hill, visited the racecourse and gathered everything they needed for Friday’s Cup. There remained only one unresolved matter from their arrival a few days earlier.
They had promised themselves a girls’ night.
A table overlooking the water seemed an entirely respectable place to begin. Unfortunately, sitting between them and the first uninterrupted glass of wine was the final field for the Port Macquarie Cup.
“Thirteen runners,” Lucy said, looking down at the form.
Sophie picked up her glass. “Then we’d better work quickly.”
Back at Race Day Co headquarters, there were apparently concerns of another kind. Ben and Jack had wandered into Tommy’s office wanting to know whether the girls were behaving themselves, whether they’d sent through any useful information and, rather hopefully, whether there was any gossip.
Tommy wasn’t concerned.
“Leave them alone,” he told them. “They’ve got Port Macquarie under control. You two have got work to do down here.”
Several hundred kilometres away, Sophie’s phone buzzed.
She glanced at Tommy’s message and showed Lucy.
Enjoy yourselves, girls. Let your hair down. I’ve got the boys under control.
Lucy smiled.
“Do you think he means that?”
“Not remotely.”
How the Cup Shapes Up
Friday’s $200,000 Port Macquarie Cup over 2000 metres has brought together an intriguing field of thirteen, and the early market suggests there is no obvious certainty waiting to collect the trophy.
Chris Waller arrives with a particularly strong hand. Medatsu, carrying 54.5kg, is the early favourite around $4 after an encouraging fifth over 1900 metres at Rosehill and looks ready to peak. Elliptical, around $4.80, brings a different form line after running well in the Wyong Cup before finishing fifth over 2300 metres in the Newcastle Cup. Back to 2000 metres and carrying 56kg, he looks particularly well placed.
Then there is Bear On The Loose. The Waterhouse and Bott runner has 58kg, but barrier six gives him every opportunity to roll forward and establish the tempo. If he is allowed to control proceedings without being pressured, those chasing him may find themselves with some work to do.
Cavalry Man presents perhaps the most compelling recent form. He comes off a strong victory over this distance in the Toowoomba Cup and, although barrier nine leaves jockey Jace McMurray with a decision to make early, a horse already winning at 2000 metres deserves respect.
Unlimited and Fioprospero add further depth, and neither looks out of place in a race where the market remains quite open.
And then, inevitably, there is an old Race Day Co acquaintance.
Look Who Followed Us to Port
King Jerry.
We have been keeping an eye on Joel Wilkes’ gelding during his road towards the Big Dance, including his recent run over 1900 metres at Rosehill. Now he turns up at Port Macquarie with 54kg, Andrew Gibbons aboard and barrier eleven.
At around $14 in the early market, he isn’t among the headline selections, and the wide draw gives Gibbons something to think about. But his recent form reads 1-8-1-2-8, and Race Day Co has learned enough about King Jerry by now not to dismiss him merely because the market has found others first.
The speed map points towards Bear On The Loose taking up a forward position, with Cavalry Man, Creative Righteous and Fays Angels also capable of being handy. That could leave several of the better fancied runners settling midfield and hoping the leader doesn’t get things entirely his own way.
For Lucy and Sophie, the homework was finally complete.
Medatsu and Elliptical gave Waller a powerful hand. Cavalry Man brought winning 2000-metre form. Bear On The Loose might prove difficult to catch if allowed his own way.
And somewhere behind them would be King Jerry, carrying 54 kilos and attempting to write another chapter in a story Race Day Co had somehow found itself following.
Sophie closed the form guide.
“Finished?”
Lucy raised her glass.
“Until tomorrow.”
This time, there was no argument.
PART 3 — THE CUP REVIEW
Cavalry Man Conquers Port
Chapter 1 — From Cocktails to Cup Day
If Thursday evening had belonged to Lucy and Sophie, Friday afternoon belonged to the horses.
The form guide that had occupied pride of place between two rather colourful cocktails was now back where it belonged, tucked beneath Lucy’s arm as the girls made their way towards the mounting yard at Port Macquarie Racecourse.
Sophie was wearing sunglasses.
Lucy had already asked twice whether they were entirely necessary.
“They’re fashionable,” Sophie replied.
“Of course they are,” said Lucy, smiling.
Whatever adventures the previous evening had produced, there was work to be done. Thirteen runners had been declared for the Carlton Dry Port Macquarie Cup, and the 2000-metre contest promised an intriguing battle between established metropolitan performers and horses arriving with winning country form.
There was particular interest in Chris Waller’s three runners, Elliptical, Medatsu and Unlimited, while Bear On The Loose looked capable of making his presence felt near the speed.
But the girls had also spent considerable time discussing Cavalry Man, the Lindsay Gough-trained gelding who arrived following his victory in the Toowoomba Cup.
Winning one Cup was an achievement. Winning another would make for quite a story.
And as the afternoon unfolded, that was precisely what he intended to do.