In 1786, the Reverend James MacGregor (1759–1830) was dispatched across the North Atlantic to establish a dissenting Presbyterian church in Pictou, Nova Scotia. The decision dismayed MacGregor, who had hoped for a post in the Scottish Highlands. Yet it led to a remarkable career in what was still the backwoods of colonial North America. Industrious and erudite, MacGregor established the progressive Pictou Academy, opposed slavery, and promoted scientific education, agriculture, and industry. Poet and translator, fluent in nine languages, he encouraged the preservation of the Gaelic language and promoted Scottish culture in Nova Scotia.

Highland Shepherd finally bestows on MacGregor the recognition that he so richly deserves. Alan Wilson brings MacGregor and his surroundings to life, detailing his numerous achievements and establishing his importance to the social, religious, and intellectual history of the Maritimes.