Rutland is the kind of place that exists almost as a joke about itself: the smallest historic county in England, abolished in 1974 in a fit of administrative tidiness, restored in 1997 because the people who lived there refused to stop calling themselves Rutlanders. Oakham, with its population of just over twelve thousand, is the county town - which makes it the smallest county town in the country and gives it the slightly unreal quality of a place that has all the institutions of a much larger settlement squeezed into a few streets around a market place. The county council sits in Catmose House. The Crown Court occasionally sits, when needed, in a Norman great hall built in the 1180s. Twice a week, the open-air market still runs in the town square, just as it has since well before any of the surrounding buildings were standing. The Buttercross, with its octagonal stone-slate roof, and the wooden stocks beside it, are both Grade I listed - the highest category of historic protection in England, normally reserved for cathedrals and country houses, here applied to a piece of village furniture for restraining drunks.

What survives of Oakham Castle is not a castle in the conventional sense. There are no towers, no battlements, no romantic ruins. There is just the great hall, sitting on raised ground within steep earthworks that once held an inner bailey. The architectural historian Nikolaus Pevsner called it 'the earliest hall of any English castle surviving so completely,' and noted that it had never really been a castle to start with - it was a fortified manor house, built around 1180-1190 for the de Ferrers family. Inside, the building is unexpectedly lovely. Romanesque carvings of musicians decorate the capitals of the piers. The roof is high, the proportions confident. Until 1970 it served as an assize court, where serious criminal cases were heard. It is still licensed for weddings, and for the occasional sitting of the Crown Court when business requires. The horseshoes line the walls in numbered rows, a peculiar gallery of obligation, with the names and dates of every royal and noble visitor recorded for posterity. Outside, the outer bailey is now Cutts Close, a small park, and the deep hollows in its grass are the dried-up stew ponds where the castle's medieval inhabitants once kept their fish.

The spire of All Saints' Church rises above Oakham for miles in every direction, a 14th-century landmark restored in the 1850s by Sir George Gilbert Scott, the same architect who designed St Pancras station and the Albert Memorial. North-east of the church, the original 1584 building of Oakham School still stands, with its south-front inscription in Latin, Greek and Hebrew that announces the school's curriculum to anyone passing by. Oakham School was founded in the same year as Uppingham, six miles south, by the same man - Archdeacon Robert Johnson - and the two schools have remained linked institutions ever since, dominant presences in their small county. Thomas Merton, the Trappist monk whose autobiography The Seven Storey Mountain became one of the 20th century's most-read works of spiritual writing, studied at Oakham from 1929 to 1932. The cricketer Stuart Broad, who took 604 Test wickets for England, was born here in 1986. So was the Paralympic sprinter Jonnie Peacock, who won gold in the 100m at London 2012 and Rio 2016 with a prosthetic running blade. The town also produced, less proudly, Titus Oates - the 17th-century perjurer whose invented Popish Plot led to the execution of dozens of innocent Catholics, and who left Oakham early.

Of all the people Oakham has sent into the world, the strangest story belongs to Sir Jeffrey Hudson, born in the town in 1619. Hudson was a person of very short stature - in the language of his own century, he was called a dwarf, and at the age of seven he stood about eighteen inches tall and was presented to Queen Henrietta Maria, wife of Charles I, who took him into her household as what court records described as her favourite. Hudson grew slowly to about three feet seven inches, fought a duel and killed a man, served the queen in exile during the English Civil War, was captured by Barbary pirates and spent twenty-five years enslaved in North Africa before being ransomed back to England. He died in his early sixties, in poverty, in London. A cottage in Oakham still bears a plaque commemorating his birth there. The full sweep of his life - from village boy to royal courtier to galley slave to forgotten old man - is the sort of biography Oakham produces and quietly keeps.

On 21 April 2024, on what would have been her 98th birthday, a bronze statue of Queen Elizabeth II was unveiled in Oakham. The seven-foot sculpture, on a limestone base, was made by Hywel Pratley and paid for entirely by local donations - businesses and members of the public contributing the £125,000 cost. It was the first memorial statue of the late Queen to be erected anywhere in the country after her death in September 2022. Rutland chose to be first not because it is wealthy, or large, or particularly important on a national scale, but because it is the kind of place that takes its small civic gestures seriously. The county has been making its own decisions, in its own quiet way, for a thousand years - paying horseshoe tributes to passing royalty, refusing to be absorbed into Leicestershire, holding markets on Wednesdays and Saturdays since the Middle Ages. The statue stands a few hundred yards from the great hall where Edward IV's horseshoe still hangs.