Calton Hill

Edinburgh's most embarrassing monument sits on this hill, and the city has spent nearly two centuries trying to decide whether to be proud of it or pretend it doesn't exist. The National Monument was meant to be a full-scale replica of the Parthenon, honouring Scottish soldiers killed in the Napoleonic Wars. Construction began in 1826, but the public appeal raised less than half of the £42,000 needed, and work stopped in 1829 with only twelve columns standing. The nicknames came fast: "Scotland's Disgrace," "Edinburgh's Folly," and the brutal "Scotland's Pride and Poverty." Multiple proposals to complete it over the following two centuries have all been abandoned.

The Nelson Monument is the hill's other landmark — a 32-metre tower shaped like an upturned telescope in honour of Admiral Nelson. Completed in 1816, it gained its most useful feature in 1852 when a mechanical time ball was added to the top. Every day at 12:58, the ball rises to the top of its mast, then drops at precisely 1pm, synchronised with the One O'Clock Gun at the castle. Sailors in Leith harbour set their chronometers by watching both: the ball for visual confirmation, the gun for foggy days.

The Dugald Stewart Monument, a circular temple modelled on the monument to Lysicrates in Athens, is perhaps the most photographed structure in Edinburgh. It honours a philosopher almost no one has heard of — but the view of the Old Town framed through its columns has appeared on more postcards and Instagram feeds than any other angle of the city. The City Observatory nearby, designed by William Henry Playfair in 1818, is one of several neoclassical structures that earned Edinburgh the nickname "Athens of the North."

At Hogmanay, tens of thousands of people climb Calton Hill to watch the fireworks explode over the castle. It's the best free seat in the house for Edinburgh's famously chaotic New Year celebration.