It was love at first sight. Frederick Douglass's surviving letters don't often depart from antislavery matters, but barely a day into his first visit to Edinburgh in April 1846, he wrote to his friend Amy Post: ‘It is a beautiful city, the most beautiful I ever saw – not so much on account of the buildings as on account of its picturesque position. I have no time even had I the ability to discribe it.’ The impression must have been a strong one, for a few weeks later, in London, he reported meeting an artist who confidently asserted that Boston was ‘the handsomest city in the world’. Douglass agreed ‘that Boston is a very handsome city, but I thought not the most handsomest in the world – and proceeded to speak of Edinburgh’, whence he was bound the following day. He was back again in the Scottish capital in July, extolling its virtues in a letter to William White. ‘The Calton Hill – Salsbury Craggs and Arthur Seat give the city advantages over any City I have ever visited in this or in your country.’ By then, he was beginning to make plans to return to the United States – later postponed, as it turned out, until the following Spring – but not before he had considered bringing Anna and the children over and settling in Britain indefinitely. If he had, it is hard to imagine him choosing to live anywhere but Edinburgh.

Douglass had rushed back to Edinburgh from London to attend the General Assembly of the Free Church on 30 May, after which he made several speeches condemning Cunningham and Candlish for refusing to cut ties with the pro-slavery churches. On Saturday 6 June, Douglass attended a special meeting at the town's Council Chambers to confer the freedom of the city upon George Thompson. The next day, Thompson and Buffum joined him as they took up an invitation to breakfast.

Picture them that Sunday morning stepping out of the York Hotel on Nicolson Street. The month had begun warm and sunny and the settled weather looked set to continue. After several weeks of intense campaigning, the three men must have welcomed the opportunity to relax and enjoy the pleasures of a leisurely stroll.