Hero of Waterloo Hotel

You are standing in front of one of the oldest pubs in Sydney, and it has a trapdoor problem. Built from sandstone quarried by convicts from the nearby Argyle Cut, the Hero of Waterloo has been pouring drinks continuously since eighteen forty-five. That is over one hundred and eighty years of uninterrupted service. The stonemason was a convict-turned-builder named George Paton, and he finished the job in eighteen forty-three to forty-four.

Now, about those trapdoors. A tunnel runs from the cellar of this pub down to the harbour. The story -- and it is well documented enough to be more than legend -- is that the tunnel was used for two purposes. First, rum smuggling: getting barrels past the customs officers. Second, something called press-ganging. Sailors or drunk patrons would be dropped through trapdoors in the floor, knocked out or too inebriated to resist, dragged through the tunnel to a waiting ship, and forced into naval or merchant service. You came for a pint and woke up on a boat to China.

The tunnel was filled in during the nineteen-sixties, but you can still see the entrance in the cellar, along with iron shackles bolted to the stone walls. The pub runs tours of the basement. Go on one.

There is also a ghost. The spirit of Anne Kirkman allegedly wanders the corridors. The story is that her husband pushed her down the pub's staircase and she has been haunting the place ever since. Staff report cold spots and unexplained footsteps on the upper floors, particularly late at night after last call.

The pub is still excellent. The sandstone walls are original, the fireplaces work, and on weekends there is live Irish music. Just watch where you step near the cellar.