The abbey of Holyrood was founded in the twelfth century. During the late Middle Ages the monastery’s guest house gradually evolved into a royal residence. In the early 1500s King James IV ordered the creation of a new palace next to the original religious buildings. His son, James V (the father of Mary Queen of Scots), continued the building work, creating an impressive Renaissance residence. In May 1544 the English sacked both the palace and abbey. The Earl of Hertford, who commanded the English forces, boasted that he left Holyrood Abbey ‘wholly burnt and desolate’.
The Netherbow Port was a great gateway controlling access to Edinburgh from the Canongate (then a separate burgh). In May 1544 it was attacked by the English, who blew the gates open with a culverin (a type of cannon with a relatively long-range). The Netherbow was remodelled in the 1570s, and a central tower seems to have been added around this date. The gateway was eventually demolished in the mid-eighteenth-century as it was a hindrance to traffic.
Trinity College and Hospital was founded by Mary of Gueldres (wife of James II) in the mid-fifteenth century. It functioned both as a community of priests and a shelter for the poor and sick of Edinburgh. The church was meant to be a large Gothic building, but only the choir and transepts were ever completed. The famous Trinity altarpiece by Hugo van der Goes is probably from this church. The Hospital survived the Reformation, but was demolished in the nineteenth century to make way for Waverley Station. Fragments of the church building were reconstructed on a new site as Trinity Apse.
St Giles' was the most important church in the burgh of Edinburgh (although it was not a cathedral until the 1630s). In 1544 St Giles' was still a Catholic Church. It was lavishly decorated with statues and stained glass, and housed the altars of the local craft guilds. The feast day of St Giles (on 1st September) was marked by a religious procession along the Royal Mile. In 1558 Protestant Reformers disrupted the religious festivities, throwing a statue of St Giles to the ground, and smashing it upon the paving stones. Two years later Scotland officially rejected Catholicism, and St Giles' became a Protestant place of worship.
The West Bow was a steep z-shaped street which formed the main route between the Royal Mile and the Grassmarket. The narrow road was shadowed by buildings with projecting galleries and overhanging upper storeys. By the early nineteenth-century the properties in the West Bow had fallen on hard times, and in 1829 it was remarked that 'few will regret their removal, to make room for modern improvements'. Only a few years later much of the West Bow was demolished to make way for the newly created Victoria Street.
The Grassmarket area is first recorded in the fourteenth century, when it was referred to as 'the street called Newbygging under the castle'. By the 1470s the area was known as 'Westirmart', and seems to have been associated with the sale of timber, hats, and shoes. At the far end of the Grassmarket stood the gateway known as the West Port, which was in existence by at least 1509, and formed the western boundary of the burgh.
The Cowgate probably developed as a street in the early fourteenth century. By the sixteenth century it was considered one of the more prosperous parts of Edinburgh. The writer and theologian Alexander Alesius (who was born in Edinburgh in 1500) claimed that Cowgate was where 'the nobility and chief men of the burgh reside'. In the early sixteenth century the archbishop of St Andrews had a residence there, which survived until Victorian times. In 1537 money was left for the establishment of a hospital and chapel dedicated to Mary Magdalen at the western end of the Cowgate. The Magdalen Chapel still exists today, although the building has been substantially altered.