Woollahra Once Upon a Time

DISCOVER THE STORIES AND SECRETS OF WOOLLAHRA’S PAST AT A TIME WHEN GREAT CHANGES ARE PLANNED FOR ITS FUTURE

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.

READY TO STEP BACK IN TIME?

Choose a date and join us for Woollahra: Once Upon a Time.

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 a Sydney Historian
Private tours available on request

GOOD TO KNOW

Where does the Woollahra tour start?

Woollahra: Once Upon a Time starts at Ulster Street, facing Oxford Street, beside St Matthias Anglican Church. The small, shady park has seating and provides an easy meeting point before we set off into the quieter streets of Woollahra.

How long is the tour and how far do we walk?

The tour lasts approximately 2.5 hours and covers around 3 km through Woollahra. We explore at a relaxed walking pace, with regular stops along the way to uncover the stories, architecture and historical details hidden throughout the neighbourhood.

Is the Woollahra tour accessible?

Woollahra is a hilly suburb, and the tour includes some unavoidable slopes and inclines as we explore its historic streets and lanes. For this reason, the route is not suitable for wheelchairs, walking frames or prams. If you have limited mobility or are unsure whether the tour will be suitable for you, please contact us before booking and we’ll be happy to discuss the route with you.

How do I get to the meeting point?

Ulster Street Reserve is easily reached by public transport, with several bus routes stopping along nearby Oxford Street. The tour finishes close to Bondi Junction, within easy walking distance of Bondi Junction Station and major bus connections.

If you’re driving, please allow extra time to find parking and check the restrictions carefully. Many nearby street parking spaces have a two-hour limit, which may not be long enough for the full tour.

What should I bring?

We recommend comfortable walking shoes and a bottle of water. Sydney weather can change quickly, so check the forecast before you set out and bring an umbrella, rain jacket, hat or sunscreen as appropriate.

What happens if it rains?

Tours generally go ahead in light rain, so we recommend checking the forecast and dressing for the conditions. If severe weather makes it unsafe or impractical to run the tour, we’ll contact booked guests as early as possible with alternative arrangements.

Are there toilets and places to sit along the way?

There is public seating at Ulster Street Reserve, where the tour begins. There are no public toilets at the meeting point or along the tour route, which takes us mainly through Woollahra’s residential streets. We recommend using facilities before arriving; nearby cafés and pubs may have toilets available to customers at their discretion.

How will I recognise my guide?

Your Journey Walks guide will be waiting at the meeting point before the tour begins and will be carrying a clearly branded Journey Walks tour folder. Please arrive around five minutes before the scheduled start time so we can check everyone in and begin on time.

Can I book a private Woollahra tour?

Yes. Woollahra: Once Upon a Time is available as a private tour for families, friends, community groups and corporate groups. Private tours can be arranged on alternative dates and times, subject to guide availability. Contact us to discuss your group and preferred date.