Jessica & Raef | Hero of Waterloo The Rocks Engagement

For Jessica & Raef, a special date night together is best spent sharing a drink at one of Sydney’s fine bars or pubs, or getting rugged up in front of the TV and watching documentaries. Raef absolutely loves history. So their first and many subsequent dates were spent in The Rocks and its surrounds with some of Sydney’s oldest alleys & buildings. Around each corner was a new story to discover.

We agreed to meet in The Rocks and Raef, of course, suggested we check out The Hero of Waterloo instead. This colonial-age building, established in 1843 is one of Sydney’s oldest pubs. Its age, though, is not what it is most famous for. Instead, its underground tunnel which runs from the cellars of the hotel to Sydney Harbour is what everyone comes to see. The tunnel was used for rum smuggling and the involuntary recruitment of sailors. Legend has it, that young men might find himself drunk at the bar, dropped through a trap door into the cellar, dragged through the tunnel, to awake next morning at sea. The maze of stone cellars beneath still bear silent witness to its treacherous past – the cold iron bars and chains of The Hero’s punishment cells, for those unruly patrons, still hang in their place.

So here is something a little bit different. An exploration of past and present. A story of love, in the midst of darkness.

Their unique story was also recently featured on Poptastic Bride. Head on over to read more about what Jess had to say about their session.

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Photography By Jonathan David

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