How the Rudder Cup shaped racing across Bass Strait
Every yachtie in Australia is likely to have a story about Bass Strait whether recounting a hairy ride in tough conditions, navigating strong currents and tides, or being frustratingly becalmed and praying for wind, while others are still dreaming about making their first crossing.
Thanks to sailors with vision and a passion for the sport, opportunities to race across Bass Strait are now an annual event, rewarded not only with priceless silverware but more importantly, a sense of pride, connection and achievement.
Today, it’s a regular occurrence for spectators to line the Port Phillip foreshore to farewell fleets making their way from Victoria to Tasmania but just how did destination sailing across Bass Strait to the Apple Isle begin?
Let’s turn the clock back to 1907.
The Melbourne to Devonport Rudder Cup is Australia’s oldest ocean race and the fifth oldest organised ocean yacht race in the world, older than the UK’s Fastnet Race and 40 years ahead of the Sydney to Hobart Yacht Race.
It is a race that has its origins etched deeply in the history books, and it all started with two mates who just loved going for a sail.
In 1907, and despite being thousands of miles apart, Thomas Day, editor of the American sailing magazine Rudder, wrote to his friend, T.A. Dickson, who was Commodore of the Geelong Yacht Club at the time, and suggested a yacht race across Bass Strait as a way of promoting the sport of yacht racing.
By all accounts, Day was a passionate sailor and sailing journalist with an affinity for amateur small boat sailing and a belief that any properly designed and maintained boat sailed by experienced crew could safely sail beyond the horizon.
In what might have been considered the sailing deal of the century, Day struck a trophy worth 60 guineas, a veritable fortune, and enough for a large house deposit at the time, and the Rudder Cup was born.
What followed was a four-entrant race that started at 6 am on the Boxing Day of 1907, with the 198 nautical mile course set from Port Phillip Heads to Low Head at the mouth of the Tamar River.
The race was sailed in very rough conditions.
Edgar Newlands, sailing with his wife and daughter, skippered the 48-foot yawl Thistle to victory, and was the first boat in history to be awarded the prestigious Rudder Cup.
Legend has it that Newland’s wife had a particularly unpleasant time and was so determined that no person be put through such a tumultuous race again, that she commandeered the Rudder Cup, with the family keeping possession of it for more than 61 years.
It was 22 years from that first race before the next race across Bass Strait was held, and in 1946, the first Queenscliff to Devonport yacht race signalled the start of annual Bass Strait ocean races.
During the 61 years the Rudder Cup trophy was in the custody of the Newlands family, other trophies were presented to race winners including the Doc Bennell Perpetual Trophy.
It took until 1968 for the Newlands family to formally present the Rudder Cup for ocean racing to the Cruising Yacht Club of Victoria, now The Ocean Racing Club of Victoria (ORCV), and the rest, as they say, is history.
Fast forward almost 60 years to 2026, and one can’t help but think how chuffed Day would be that fleets still line up on the start line in Queenscliff as skippers pit their wits, boats and sailing skills against each other as they compete for the prestigious Rudder Cup.
The sport of yachting and offshore racing has come a long way since 1907 in boat design, building materials, safety, technology, sails, communication and navigation, but what hasn’t changed is that passion and partnerships are still what’s needed to bring new ideas to life.
In what is an exciting next chapter for ocean racing, the ORCV, the stewards of ocean racing in Australia, have joined forces with the Port Dalrymple Yacht Club (PDYC) to launch the Bass Strait Cup.
This new interstate sailing trophy recognises performances across two Bass Strait offshore races, the Melbourne to Devonport Rudder Cup and Tasmania's Three Hummock Island Race (hosted by the PDYC), with the aim to encourage greater participation between the Victorian and Tasmanian fleets, while celebrating a shared passion for offshore sailing in Bass Strait.
Robert Cassidy, a 77-year-old retired marine engineer from Tasmania and life member of the Tamar Yacht Club, is a veteran of the Rudder Cup, having sailed his boats Rampant and Tartan across Bass Strait in close to ten races, while also crewing for mates along the way.
Rampant pressing hard across Bass Strait int the Rudder Cup. Photo: Richard Bennett
Robert Cassidy and the crew of Rampant were presented with the Goliath Trophy for first Tasmanian boat home in the Rudder Cup. L to R: Andrew De Witt, Peter Hesketh, Robert Cassidy, Paul Herron, the late Tony Rundle AO, Doug Jack (dec.) and Ian Tilley, on the front lawns of the Mersey Yacht Club. Credit: The Advocate
Talking with the ORCV, Cassidy described how he and his crews have “thoroughly enjoyed pushing the boats hard as we [sic] galloped across Bass Strait …it’s a nice short ocean race and I enjoyed it immensely”.
Cassidy, a keen reader of stories about sailing offshore in older vessels, described many of the improvements that have been made in ocean racing since the first race in 1907.
“Those older vessels were all timber, and a lot of them used to leak like sieves, especially in rough conditions, unlike a modern boat which is pretty water-tight.
“In those conditions, what they encountered would have been horrendous compared to what we encountered, but if you have the right vessel, there are so many regulations now, such as storm jibs and trysails that you have to have on the boat, that if you manage the boat correctly, you [mostly] won’t be in any great danger, unless you happen to be broached by some very big seas.
“In the older boats, they weren’t travelling at the speeds that we were doing – a lot of the old ketches and yawls would just drop their headsails and mizzens and just go on mainsail, heavily reefed, they could slow right down and still be reasonably safe.
“Navigation was a real problem back then compared to now as you were relying on set and drift, there were no aids to navigation, you just had a compass course to steer to,” said Cassidy.
To sailors contemplating the Rudder Cup for the first time, Cassidy’s advice is not dissimilar to the perspective of Thomas Day, which is … “find yourself a good skipper and a good yacht and go for it!”.
Nick McElwee, skipper of the Hick 35 Honeypot from the PDYC, is the first Tasmanian entry in the 2026 Rudder Cup and is busily getting his crew together for the Category 2 race, which will include newly elected PDYC Commodore, Nerissa McElwee.
“One of the reasons we are sailing in this race is that you don’t often come across races of this age, with so much nostalgia and history around them,” said McElwee.
McElwee sees the addition of the Bass Strait Cup as an important initiative to encourage boat owners to reach and maintain Cat 2 compliance to be ready to race for new trophies like these.
“We got the boat ready for the Rudder Cup, which is a Cat 2 race, and have kept it there, so adding the Three Hummock Island Race is easy for us.
“Ocean racing has really lacked in the north, with ageing boat owners, and youngsters not buying boats as much, so the Bass Strait Cup is a great initiative, and while not everyone will be ready to sail this year, I know there are boats that are working to get their boats to Cat 2 level,” said McElwee.
The 2026 Melbourne to Devonport Rudder Cup is a 195 nautical mile race across Bass Strait, from Queenscliff to Devonport, now sailed in late October.
Jamieson Marshall, at 25 years possibly the youngest Commodore in the history of the Mersey Yacht Club, is excited about hosting the fleet as they arrive in Devonport from the 31st of October.
Marshall describes the Rudder Cup as a “good stepping stone especially for younger sailors who get to sail in a fairly short race across Bass Strait for the first time.
“It’s pretty amazing to me that the Rudder Cup is over four times as old as I am, so to be playing a small part in hosting this race with its overwhelming history is exciting.
“In Devonport, it’s all hands-on deck for us with the ORCV - it’s a big event for the Mersey Yacht Club; we are looking at 20 to 30 boats coming over from Queenscliff, which will fill our marina and our club house.
“Our volunteers are always ready to do whatever they can to ensure that the visiting yachts have a great finish to their race,” said Marshall.
For more information and to enter the 2026 Melbourne to Devonport Rudder Cup Yacht Race, which is a qualifier for several ocean races including the Melbourne to Hobart Yacht Race, go to: https://www.orcv.org.au/devonport
Prowler, skippered by Joe Westerlo, holds the race record of 19h 32m and 56s which was set in 1998. Photo: Prowler crew
ORCV Media/Jane Austin
