A view of Sydney, Cape Breton Island, Nova Scotia, looking east from its harbour, then called Spanish River – the inlet leading to Spanish Bay about twelve miles to the north. The town was founded in 1785 by the military cartographer Captain (later Colonel) J.F.W. Des Barres, on the site of a previous small French settlement. Des Barres was made British lieutenant-governor of Cape Breton from 1784 but only arrived at Sydney in January 1785. After local dissensions and debts he ran up, he left for England on 13 October 1787 and only returned to Nova Scotia after his final posting (1804-12) as lieutenant-governor of Prince Edward Island. He was succeeded at Sydney by Colonel William Macarmick who remained resident there into the mid-1790s. The location is confirmed by early maps which show the Barracks (constructed 1785-86) as the largest structure on the headland on which the town was built. The inscription 'No.1' in the top right of the wash-line surround also shows the drawing was one of a series (the others not present in the collection). The British flag flying at centre is a white ensign (only a naval squadronal colour at this time) which is not easily explained unless possibly flying in compliment to the temporary presence of Herbert Sawyer, commander on the Halifax N.S. station, who was ranked Rear-Admiral of the White,1787-90. The draughtsman may have been a visiting naval officer at Sydney or a resident army one: both were trained to make this type of view, though the sky and sea are more artistically rendered than in many such examples. If a military artist, the style suggests he could have been trained by Paul Sandby, who was drawing master at the Royal Military Academy at Woolwich, 1768–96. On Wednesday 8 October 1788, during his late Canadian cruise as captain of the frigate 'Andromeda', Prince William Henry (later William IV) made a visit to Sydney, of which there is informal account in the journal of Lieutenant - later General - William Dyott (1761–1847) who accompanied him. Dyott notes that before sailing up river the Prince visited to the coal mines closer to Spanish Bay, which were a main source of local revenue, and reports that Sydney was then garrisoned by part of the 42nd Regiment (the Black Watch) under Lt-Col. [Charles] Graham, who dined on board with them. He makes no reference to Macarmick as lieutenant-governor, only Des Barres (already gone), but may have confused the two. ‘The town’, he continues, ‘…consists of about fifty houses… surrounded to the very sides of the buildings by an almost impenetrable wood. There is a narrow path from the barracks just to keep up a communication, and that’s all the clear country I saw. The barracks are shamefully bad; the troops have cleared a good parade [ground] and made themselves as comfortable as their situation would allow. The officers had no rooms in the barracks, and were obliged to build huts and log-houses.’ On Monday 13th the Prince and Dyott dined on the other side of the harbour with 'Mr Cayler' (Abraham Cuyler), ‘secretary to the Government of Cape Breton. We had a good dinner, and got outrageously drunk, Prince and subject.’ 'Andromeda' left on Thursday 16 October, returning to Halifax, after ‘a very pleasant week [and] rather more wine than was good for our constitutions’. (‘Dyott’s Diary, 1781–1845…’, ed. R. W. Jeffery [1907], vol. 1, pp. 58–59). An even more uncomplimentary 1789 account of the town and its economy by an anonymous army writer appears in Brian Tennyson's 'Impressions of Cape Breton' (1986) pp. 60-61. This drawing appears to be part of the Macpherson Collection, acquired in 1928: it has long been filed amid images of Sydney, New South Wales, equally long assumed to be one, and was only correctly identified in November 2017.