Boswell wrote in his Journal of a Tour to the Hebrides that on August 21, 1773, he and Dr Johnson "met Mr Gleg, a merchant here [in Montrose]. He went with us to see the English chapel." The identifiation of "Mr. Gleg" with Adam Glegg is likely if not absolutely certain.

Boswell and Dr Johnson stopped by Leuchars on their journey from St Andrews to Montrose on August 20, 1773, having noticed the church tower from the road. Boswell wrote, in his Journal of a Tour to the Hebrides:

The manse, as the parsonage-house is called in Scotland, was close by. I waited on the minister [James Walker], mentioned our names, and begged he would tell us what he knew about it. He was a very civil old man; but could only inform us, that it was supposed to have stood eight hundred years. He told us, there was a colony of Danes in his parish; that they had landed at a remote period of time, and still remained a distinct people. Dr Johnson shrewdly inquired whether they had brought women with them. We were not satisfied as to this colony.

Walker, referred to by Boswell only as a very civil old man, died just a few months after their visit.

On August 20, 1773, Boswell and Johnson went with Professor Andrew Shaw to see Colonel Nairne's garden and grotto, a feature in St Andrews, now long since lost. Boswell described it as follows, in his Journal of a Tour to the Hebrides:

Here was a fine old plane tree. Unluckily the colonel said, there was but this and another large tree in the county. This assertion was an excellent cue for Dr Johnson, who laughed enormously, calling to me to hear it. He had expatiated to me on the nakedness of that part of Scotland which he had seen. His Journey has been violently abused, for what he has said upon this subject. But let it be considered, that, when Dr Johnson talks of trees, he means trees of good size, such as he was accustomed to see in England; and of these there are certainly very few upon the EASTERN COAST of Scotland. Besides, he said, that he meant to give only a map of the road; and let any traveller observe how many trees, which deserve the name, he can see from the road from Berwick to Aberdeen. Had Dr Johnson said, 'there are NO trees' upon this line, he would have said what is colloquially true; because, by no trees, in common speech, we mean few. When he is particular in counting, he may be attacked. I know not how Colonel Nairne came to say there were but TWO large trees in the county of Fife. I did not perceive that he smiled. There are certainly not a great many; but I could have shewn him more than two at Balmuto, from whence my ancestors came, and which now belongs to a branch of my family.

 

The grotto was ingeniously constructed. In the front of it were petrified stocks of fir, plane, and some other tree. Dr Johnson said, 'Scotland has no right to boast of this grotto: it is owing to personal merit. I never denied personal merit to many of you.' Professor Shaw said to me, as we walked, 'This is a wonderful man: he is master of every subject he handles.' Dr Watson allowed him a very strong understanding, but wondered at his total inattention to established manners, as he came from London.

Craig was a contemporary of Boswell's, being of almost the same age (Craig being one year older than Boswell). Both were born in Edinburgh, and they died within a few months of each other in the Summer of 1795. They moved in the same circles, and Sir William Forbes was a close friend and confidante to both of them.

On August 19, 1773, Craig dined with Boswell and Dr Johnson at the house of Dr Robert Watson in St Andrews. He is known to have worked on refurbishing St Salvator's and St Leonard's colleges in St Andrews at the time, which explains his presence in the town. Boswell described the occassion in his Journal of a Tour to the Hebrides as follows:

We all went to Dr Watson's to supper. Miss Sharp, great grandchild of
Archbishop Sharp, was there; as was Mr Craig, the ingenious architect
of the new town of Edinburgh, and nephew of Thomson, to whom Dr
Johnson has since done so much justice, in his Lives of the Poets.

.

Shaw breakfasted with Boswell and Dr Johnson in St Andrews on August 20, 1773, during which Boswell took out his copy of Ogden on Prayer and read some of it to the company. After breakfast, they went together to see "Colonel Nairne's garden and grotto". 

In his Journal of a Tour to the Hebrides, Boswell mentions how Shaw said of Dr Johnson, that he was a "wonderful man: he is master of every subject he handles." Johnson later returned the compliment, telling Boswell that he "took much to Shaw."

Boswell and Johnson dined with Hadow (referred to by Boswell as Haddo) and several other professors at the University of St Andrews on August 19, 1773. In the afternoon, Hadow walked with them. Also present was Dr Watson, at whose house they had lodged the previous night.

Boswell and Johnson visited Principal Murison (as he then were) at St Mary's College at St Andrews on August 19, 1773, on the first leg of their tour of Scotland. Boswell wrote of the occassion that "[the college has] a good library-room; but the principal [Murison] was abundantly vain of it, for he seriously said to Dr Johnson, 'you have not such a one in England'."

Boswell and Johnson lodged at Dr Watson's at St Leonard's College in St Andrews on August 18-19, 1773, on the first leg of their tour of Scotland. They were introduced to Watson by William Nairne in the morning of the 19th, and Boswell, in his Journal of a Tour to the Hebrides, described him as a "a well-informed man, of very amiable manners."

Later that day, Boswell and Johnson dined with Watson and several other professors at a local inn, and in the evening, they supped at Watson's together with a "Miss Sharp, great grandchild of Archbishop Sharp" and "Mr Craig, the ingenious architect of the New Town of Edinburgh."