MacGregor attended medical school in Edinburgh and held several hospital positions in the city before being called up for National Service.

[1] Following his death, a Stuart MacGregor Memorial Prize was established by Edinburgh's Department of Community Health.

[2] In 1958, with Hamish Henderson, MacGregor co-founded the Edinburgh University Folk Society and was its first President.

[3] He wrote a number of widely recorded folk songs about Edinburgh life including the humorous "Sandy Bell's Man" about dating medical students, and the romantic "Coshieville."

This featured the work of four Scottish poets, the others being Sorley MacLean, George Campbell Hay and William Neill.