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The site of a cattle market from the 15th century until the start of the 20th century, the Grassmarket has always been a focal point of the Old Town. It was once the city's main place of execution, and over 100 martyred Covenanters are commemorated by a monument at the eastern end, where the gallows used to stand. The notorious murderers Burke and Hare operated from a now-vanished close off the western end.

Nowadays the broad, open square, lined by tall tenements and dominated by the looming castle, has many lively pubs and restaurants, including the White Hart Inn, which was once patronised by Robert Burns. Claiming to be the city’s oldest pub in continuous use (since 1516), it also hosted William Wordsworth in 1803. Cowgate – the long, dark ravine leading eastwards from the Grassmarket – was once the road along which cattle were driven from the pastures around Arthur's Seat to the safety of the city walls. Today it is the heart of Edinburgh's nightlife, with around two dozen clubs and bars within five minutes' walk of each other.