Mr Gregory married Nancy Ford Reely in 1879 and she seems to have given him magnificent support enabling him to become the figure of great public significance that he was. In his early Headships she was the Mistress-in-charge of the younger children. Later she is recorded as feeding generous meals to the pupil-teachers who had come for an evening's instruction from their schoolmaster. In Gregory's journalistic output the fictitious "Philosopher" has the homely wisdom of a good wife. Gregory was of "a peaceable turn of mind" and took great pleasure in gentle country rambles with his wife. Early Sunday morning was a favourite time, when birds sang "a song of the triumph of peacefulness over the noise and turmoil of this materialistic age.
Together Mr and Mrs Gregory raised a flourishing family, Richard Walter, and Arthur John (Jack) and mourned the loss of Frederick Hugh, aged four, who died of smallpox in 1890.
Written comments and expressions on faces in family photographs betray a real pride in his children and his grandchildren. The feeling was mutual and it enabled his sons to build careers of their own, Richard Walter as an Electrical Engineer on Tyneside. Mrs Gregory enjoyed only a year of retirement with her husband before her death in 1921.
With his family, Mr Gregory seems to have chosen deliberately to live in places "steeped in history" but in the convenience of a modern home, where possible. North Cadbury had an Elizabethan manor house, a perpendicular church and an ancient hill-fort nearby associated romantically with King Arthur's Camelot. Castle Cary has the foundations of a Norman Castle and, in the market place, an 18th century lock-up. There the Gregorys lived first in Fore Street, above a baker's shop, and then at "Bellevue" in South Cary. Eltham has a Medieval Palace and a Tudor Barn. There they lived in the school-house for nearly nine years and then moved to 4, Wellington Road, now Wythfield Road. Holidays were often taken in Hexham, Northumberland, with its famous Medieval Abbey and adjacent to Hadrian's Wall. R.R.C. Gregory used these historic environments creatively. It took painstaking research and much meditation and imagination.