John Cleeland arrived in Victoria from Northern Ireland in 1840. 

After years of sailing, he became a captain of his own schooner and returned to Melbourne in 1859 to purchase the Albion Hotel in Bourke Street, a business he kept for 22 years.

In the early 1870s he purchased several allotments on Phillip Island (as well as the Western Port hotel in San Remo), one of which is where Woolamai House now stands. John Cleeland used the property to train his racehorses.

Captain Cleeland’s keen interest in horse racing saw him buy and train the racehorse Wollomai, which had been bred by John David McHaffie. 

Such was Cleeland’s devotion to horse racing, he walked his horses from Phillip Island to Melbourne to compete in races.

Wollomai won the Melbourne Cup in 1875, after having completed the 140km walk only days before. It was the first time the Cup was run on a Tuesday.

Cleeland supposedly won up to 20,000 pounds from Wollomai’s win.

In a recorded interview with the Phillip Island Historical Society, Captain Cleeland descendant Ted Jeffery recalled that “some of great grandfather’s horses were stolen from Euroa by the Kelly gang and ridden to New South Wales”. 

“But they were never any good after that as they had been ridden too hard,” Ted said.