Most country trainers agree it’s no pushover to win a TAB Highway. For a start they have to identify the right horse for the job and plan their programmes meticulously. With capacity fields certain most weeks the bush horsemen wait with bated breath for the crucial barrier draw. Some choose not to undertake a long road trip if their horses fare badly at the gate. Those that do decide to go ahead, can only hope their horses cope with the travelling. It’s a rare country trainer who doesn’t have the fingers crossed as he or she takes up a position to watch the running of yet another TAB Highway.
With so many variables at play, Stirling Osland is one trainer who does his homework thoroughly before committing to a punishing 600 km haul from Armidale to Randwick or Rosehill. Many punters have already worked out that Stirling doesn’t subject himself or his horses to what he regards as a futile mission. This is the reason his genuine three year old filly Calico Miss started a solid second favourite at $4.60 in Saturday’s TAB Highway. Not surprisingly her emphatic win gave the astute New England horseman his fifth success in the prized weekly series for bush horses. It was great to get our fifth Highway especially at Royal Randwick,” said Stirling. It’s a thrill to win anywhere, but there’s something about that place.”
Calico Miss had TAB Highway written all over her when she cantered home in a BM58 at Scone 10/06/2025 - courtesy Bradley Photographers.
The trainer harboured mixed feelings when Calico Miss came up with the inside gate at acceptances last Thursday. “The inside draw can be a hindrance more than a help on occasions,” said Stirling. “This filly can still be a little bit chancy coming out of the gates, and I was worried that an ordinary start would put her too far back in the field of fourteen. Against that is the fact that Mikayla Weir knows her backwards. She’s ridden her right through and is familiar with her few little quirks.”
Stirling needn’t have worried. While not the best out, Calico Miss quickly cruised through to settle behind joint leaders Satin Stiletto, Pretty Vegas and She Within. Just as Mikayla Weir began to think about a way out of the pocket, Satin Stiletto left the fence abruptly leaving a gaping hole for Calico Miss. The Armidale filly darted through to grab the lead on top of the rise from Satin Stiletto who was in for a stoush. Favourite Exit Fee was starting to extend from well back in the field, with nothing else on the scene. At the 100m mark Satin Stiletto shifted in abruptly and heavily contacted the hind quarters of the leader. Not only did the impact further motivate Calico Miss, but the head-on footage reveals that she came out slightly to give Satin Stiletto a bit of her own back. She hit the line tigerishly to beat Exit Fee and Satin Stiletto, taking her record to three wins and a second from just four race starts.
Little Calico Miss defied Exit Fee to win Saturday's TAB Highway - courtesy Bradley Photographers.
Calico Miss isn’t the first horse Stirling has trained for Stuart Ramsey. The larger than life cattle exporter, auctioneer and horse breeder got serious about the thoroughbred business when he purchased Turangga Stud near Scone from the Redmond family in 2003. Stuart has raced many a good horse with some of Australia’s most high profile trainers but has always managed to put one or two aside for young Stirling Osland whose father Rudd has been one of his closest friends since college days. Stirling actually prepared Chain Of Lightning for her first two starts in 2022 resulting in a maiden win at Inverell and a Cl 2 success at Armidale. The mare later went to Peter Moody for whom she won another six races including a Gr 2, two Gr 3’s and the Gr 1 TJ Smith last year defeating luminaries Bella Nipotina and I Wish I Win. Stirling was understandably chuffed that Saturday’s Highway success was his first metropolitan win for Ramsey Pastoral Pty Ltd.
Stirling Osland was the trainer when Chain Of Lightning won her first two races. Here's the second win at Armidale with Brooke Stower 24/01/2022 - courtesy Bradley Photographers.
The Calico Miss pedigree is of interest to breeding buffs. Her sire Better Land is by the celebrated Shamardal who shuttled to Australia early in his stud career. Better Land’s dam Amelia’s Dream (Redoute’s Choice) was being touted as a live Golden Slipper prospect after two massive wins in the early autumn of 2008. She won a Canterbury 2YO maiden by almost ten lengths and the Silver Slipper by more than six before a serious injury terminated her career. Better Land was no Amelia’s Dream but possessed enough ability to win four races and finish a respectable second to Scissor Kick at stakes level in The Rosebud of 2014.
Calico Miss is a daughter of the unraced Region (Hinchinbrook), and her second dam Bukhoor (Jeune) also failed to make it to the races. Third dam Nasmah (At Talaq) was a three time winner in Victoria while fourth dam Asawir was another racetrack absentee. The fifth dam of Calico Miss was the enormously influential Easy Date (Grand Chaudiere) whose eleven winners included Gr 1 winner Quick Score and celebrated sprinter Snippets, winner of three Gr 1’s before embarking on his distinguished stud career.
Stirling Osland’s association with horses began on the family farm near Tamworth where polo ponies and campdrafters played a major role in his early years. On completing his education in the mid 2000’s young Osland decided to appease his curiosity about that great tract of land in Central Australia. He would spend almost six years working on cattle stations around the Northern Territory, an experience he cherishes to this day. It was then back to NSW where his father Rudd recommended him to Stuart Ramsey as a prospective staff member for Turangga Stud in the Hunter Valley. “I’ll always be grateful to Stuart for the wonderful start he gave me at Turangga,” said Stirling. “I get a big kick out of winning a race for him anywhere. Imagine what a buzz it was to win our first city race together on Saturday and at Randwick of all places.”
Stirling Osland has been around horses all of his life but only began training in 2014 - courtesy Bradley Photographers.
To this point in his life Stirling had thought little about racehorses, but from the moment he joined the Turangga team a new love affair began. He participated in the many phases of stud management but took special interest in the breaking and educating of yearlings. He turned out to be an absolute natural in the field and has continued to hone his skills to this day. From Turangga Stud the skilful horseman headed south when a job came up at the former Eliza Park Stud, now rebranded as the Sun Stud. More horses, more experience and a burgeoning fascination with the thoroughbred.
Still eager to learn, young Osland drifted back towards his native New England region and found employment at Gerry Harvey’s long established Broombee Stud. Around three years later he felt confident enough to consider a serious “crack” at the training business. He was just 25 but already a veteran in the art of horse management with a special flair for the breaking of yearlings. He knew it wouldn’t be easy and expected little. He wondered if he’d made the right decision at Tamworth on September 9th 2014, when his very first starter Harlequin’s Gold finished 18 lengths from the winner in a BM 55. Something told him to put it aside and move on. Four months and a handful of runners later, trainer S. Osland got on the board with New Endeavour in a 2YO Maiden Plate at Gunnedah.
Unplaced at his next two starts, New Endeavour (not to be confused with the imported horse of the same name in the Waterhouse/Bott yard) parted company with the Osland stable to join the Corstens team in Melbourne. He wasn’t there long. He finished last of eight at Geelong at his only Melbourne run, and within a week had turned up at the Waller stables in Sydney.
He didn’t race at all for the premier stable and suddenly arrived in the Jason Coyle stables at Warwick Farm. In ten starts for Coyle he won races at Wyong and Kembla, before being returned to his original trainer at Armidale. The son of Casino Prince obviously enjoyed the crisp New England air because he reeled off another seven wins on Stirling Osland’s watch. “There’s no doubt he was the horse to put me on the map,” he said. “Rage Against was another great bush horse for the stable. He won eight races, most of them up this way but he did sneak down to Wyong one day and knocked one over.”
New Endeavour in one of his eight wins for Stirling. This was an Open Hcp at Gunnedah 17/12/2019 with Ashley Morgan - courtesy Bradley Photographers.
Stirling’s quintet of TAB Highway wins has brought him under notice as a bush trainer of obvious talent. Prada Miss put him on the board with a Highway win at Rosehill in 2017. About eleven months and very few starters later, Radiant Choice prevailed for the young trainer again at Rosehill. Point Counterpoint carrying the Matthew Sandblom colours was his third Highway winner on Gong day at Kembla Grange in 2021. In February 2022 Matthew Sandblom’s Golden Point scored the gutsiest of wins at Rosehill to bring up Highway number four for Osland. Calico Miss made it five on Saturday.
Stirling’s team fluctuates between 20 and 25 horses all year round. The racehorses are stabled on course at Armidale, but spell at his 100 acre property on the outskirts of town where Stirling lives with wife Courtney and three year old daughter Heidi. The trainer frequently gives his racehorses two or three days on the farm in the wake of a tough run. Between training and racing commitments he finds the time to break in young thoroughbreds for new and existing clients. It’s not uncommon for Stirling to break in and educate 40 horses or more over a full year. Spare time to this dedicated horseman, is a very rare commodity.
Stirling on his way to the horse stalls to saddle up a runner at a northern NSW meeting - courtesy Bradley Photographers.
The Stirling Osland technique works and works well. He recently completed his first decade in the training ranks and is nudging 200 wins with rarely more than twenty horses in work. He’s been around horses of multiple breeds for all of his 36 years and understands the language of the animal. There’s no doubt they understand him too.
(Banner image - Calico Miss had a quick squiz at the infield camera as she raced home in the TAB Highway - courtesy Bradley Photographers.)