Woollahra: Once Upon a Time - A history walking tour

Once upon a time in Woollahra

Colonial mansions stood in sprawling gardens, shopkeepers, servants, artists, tradesmen and society figures shared the streets of a rapidly growing village, and the landscape itself was still being tamed.

Beneath the elegant villas was a surprisingly wild terrain of sandstone ridges, gullies, streams and dense pockets of bush. One early observer thought Woollahra’s natural beauty required “a great deal of modern dressing” to make it suitable for suburban life — and traces of that unruly landscape still shape its streets today.

Rewind and explore

At one end of the suburb, ironwork left Fletcher’s foundry destined for the terraces and villas of Sydney, while barrels of Resch’s beer made their way from a local brewery towards the city’s thirsty pubs. At the other, steam trams, omnibuses and private carriages passed the grand sandstone gates of Centennial Park, carrying residents and visitors along roads where horses had once struggled through mud and ruts. Between them grew the Woollahra we recognise today — estates became streets, corner shops opened, houses crowded onto the hillsides and an increasingly fashionable village took shape.

Quirks and characters of Old Woollahra

You might bump into Banjo Paterson trotting down Queen Street on horseback, encounter policemen from Paddington, pistols drawn, racing through the back streets in pursuit of a jewel thief, or discover that your next-door neighbour was a secretive scientist milking venom from deadly snakes in his backyard laboratory. Look skyward and you might even see an Edwardian aeronaut descending in his balloon onto a quiet residential avenue after scattering thousands of flyers over Sydney.

Honouring local heritage

Wander beneath towering trees and along shady side streets, learning to read the clues left behind in sandstone villas, Victorian terraces, old shopfronts and iconic Art Deco flats. Discover artists and eccentrics, dramatic crimes and extraordinary everyday events, traces of vanished industries and transport routes, and the stories of residents who fought to preserve places that might otherwise have disappeared.

With significant change again on Woollahra’s horizon, this is a timely chance to look closely at the suburb we have inherited — to understand how it came to be, what has already been lost and changed, and just how much of old Woollahra is still hiding in plain sight.

At a glance

• 2.5 hr walking tour

• approximately 3 km covered

• Small groups of max. 15 people

• $58 per person

• Led by local Sydney historian

• Private tours available on request