Unknown to many, this passage is a short-cut between Edinburgh’s Waverley Railway Station parking lot and the touristic Calton Hill.

A Jacob's Ladder is an 18th-century term that refers to the biblical story of Jacob and his dream of a rope step ladder stretching up to Heaven. The origins of Edinburgh's Jacob Ladder are first recorded in an article written in 1784, though it is thought to be much older than that.

This pathway, which cuts through volcanic rock, is thought to have had many different uses and configurations over time. Prior to the construction of the North Bridge in the mid-1700s, which connects the High Street with Princes Street, there weren't many ways for someone to get from the Old Town to the New Town. Jacob's Ladder allowed people and goods the ability to get in and out of the city more efficiently, without having to travel greater distances. This was especially handy because at the time, the Nor Loch, a body of water stretching along the full distance of Princes Street, prevented access to the docks in nearby Leith.

This trail also allowed mourners to get to the Old Calton Burial Ground, and was most likely the route prisoners were taken to reach the former Bridewell Jail. Tourists have been clambering up these steps for centuries to get unparalleled views of the castle, the city, and access to the monuments atop of Calton Hill. In 2018 and 2019, Edinburgh World Heritage invested £150,000 to transform the steps, which had fallen into disrepair.