Uppingham was situated in a county which was a good deal more than a howling wilderness. In its structure and outlook, Rutland was quintessentially rural: it might even be described as still feudal. Of its 96,000 acres, nearly 79,000 (82 per cent) were under cultivation of some sort – with 42,000 acres given over to arable and 36,000 to pasture. Landed interests predominated everywhere, and landowners were unlikely to be sympathetic to rapidly rising rates.

The influence of the leading members of the Rutland gentry was exercised largely through the ownership of land and property. Walford's list for 1876 names 35 families who represented the core of Rutland society, and although its diminutive size makes statistical comparisons with other counties suspect, an indication of Rutland's character is seen in the fact that it had one country house for every 31,000 acres – the highest such distribution of any English county. Four of the 331 greater landowners in the modern Domesday Book (the so-called blue book) of land ownership, drawn up by John Bateman in 1873, had 9,000 acres or more in Rutland, and between them they owned half the county. Two of them had their chief seats in Rutland, and the other two were just across the border in Lincolnshire. Apart from Rutland, only Northumberland as a county had more than half its acreage in the hands of owners of 10,000 acres or more.

Bateman also records the names of owners of land of more than 3,000 acres with a gross annual value of over £3,000. Of Rutland's total acreage, over 70 per cent (66,294 acres) was owned by one peer, five ‘great landowners’, and five squires. No fewer than four of this elite group were trustees (governors) of Thring's school: the Earl of Gainsborough (who lived at Exton Park), Sir John Fludyer (Ayston Hall), George Finch MP (Burley-on-the-Hill) and John Wing-field (Tickencote Hall). Below them, a further 10,017 acres were owned by ‘great and lesser yeomen’ or medium-sized farmers.