Uppingham is built almost entirely of the warm orange-brown ironstone that comes from the surrounding quarries. The High Street widens into a market place lined with shops, pubs, the Falcon Hotel, the Methodist Chapel of 1819, and the substantial 14th-century parish church of St Peter and St Paul. Just over a mile to the north-west, at Castle Hill, are the earthwork remains of a medieval motte and bailey - the original lord's fortification, abandoned and ploughed for so long that only the shape of the ground records what once stood there. The town never grew large. With under five thousand inhabitants today, it still has the proportions of a place sized for the regular weekly market rather than for any subsequent industrial purpose. Once a year, in November, the market place is transformed into the only fatstock show still held in temporary penning in a traditional English market town. The 2011 show had 140 sheep, 24 pigs and 20 cattle entered. The first recorded show was in 1889. Farmers exhibit, judges judge, and afterwards everybody adjourns to the Falcon for a drink.

Uppingham Workhouse first appears in records in 1777, when it had space for forty inmates - the parish providing what amounted to last-resort housing for the destitute. After the New Poor Law of 1834, the system was reorganised, and in 1836 the Uppingham Poor Law Union built a much larger workhouse on Leicester Road to house 158, designed by the architect William Donthorne. The building still stands. It is now Constables, a girls' boarding house at Uppingham School - a transformation that captures something of the town's history in a single building. During the First World War, the workhouse served as an auxiliary hospital staffed by a Voluntary Aid Detachment. It closed in 1929 and was taken over by the school in due course. The same physical structure that once received the desperate and the destitute now houses the teenage daughters of professional families who can afford forty-five thousand pounds a year in school fees. England works that way.

Three miles south of Uppingham, near the village of Eyebrook, lies a reservoir that looks unremarkable on any map. In May 1943, the Eyebrook Reservoir became one of the key practice sites for one of the most famous - and most controversial - bombing missions of the Second World War. The Avro Lancasters of 617 Squadron, flying from RAF Scampton in Lincolnshire under the command of Wing Commander Guy Gibson, used Eyebrook to rehearse the low-level approaches and timed bomb releases they would need for Operation Chastise: the attack on the Ruhr valley dams on the night of 16-17 May. The mission breached the Möhne and Edersee dams using Barnes Wallis's bouncing bombs, flooded thousands of acres of German industrial heartland, killed an estimated 1,600 people - many of them forced labourers and prisoners of war - and was immortalised in the 1955 film The Dam Busters. Eight of the nineteen Lancasters that took off did not return. The reservoir at Eyebrook is now a fishing lake popular with anglers, and it carries no marker for what was practised over its calm surface in the spring of 1943.

For a town of fewer than five thousand people, Uppingham has an unusual concentration of art galleries. The most prominent is the Goldmark Gallery, which has been operating from the same High Street premises for over forty years and holds more than fifty thousand items in its stock - prints, paintings, ceramics, books. The gallery's reputation extends well beyond Rutland; collectors and dealers travel to Uppingham specifically to see it. Smaller independent galleries cluster nearby, giving the town the character of a place where serious art is bought and sold in proportions that would be normal in a much larger settlement. The Uppingham Town Partnership, a volunteer-run community group, organises the annual Uppingham Feast Day in June, a Christmas late-night shopping event in December, and the Uppingham in Bloom committee that has won multiple gold medals in the national Britain in Bloom competition. None of these things are unique to Uppingham. What makes the town distinctive is the way the small population sustains all of them simultaneously, while also running a fatstock show and an internationally-known boarding school and a Friday market that has not missed a week in seven hundred and fifty years.

Uppingham once had its own railway station, opened in 1894 at the end of a short branch line from Seaton, just inside the Rutland border. The station sat at the bottom end of Queen Street, on the southern edge of the town. Passenger services were withdrawn in 1960 - victims of the post-war collapse in rural rail traffic that anticipated the Beeching cuts - and the line closed completely in 1964. The station yard was redeveloped as an industrial estate, and the line itself has long since been lifted. Today the nearest station is at Oakham, six miles north, or Corby, nine miles south. The A47 bypass, opened in June 1982, takes through-traffic around the town centre and has preserved the High Street from the worst of modern road life. Buses still run to Leicester, Peterborough, Stamford, and Oakham. Mostly, however, Uppingham is a town you arrive at deliberately rather than pass through - which, for a place that has been quietly resisting modernity for centuries, suits it very well.