The Vaults sits on the Market Place in a fifteenth-century building, and on a cold day the log-burner does most of the talking. It is Grade II* listed, runs five hand pumps with two guest beers usually from local breweries, and puts on gourmet burgers alongside the rest of its food. Dogs are allowed all day in the downstairs bar. It offers rooms if you want to stay above the town rather than beside it.
The Market Place is Uppingham's commercial and social hub, and two more inns frame it. The Falcon Hotel is a sixteenth-century coaching inn with log fires, oak-beamed private dining and gardens out the back, one of the landmark buildings that give the square its shape. A short walk up the High Street, the Crown Inn is another former coaching house, serving home-cooked food sourced where it can be from local independents, with live music at weekends. It won Rutland CAMRA Pub of the Year in 2014. For something different, Don Paddy's is a Spanish tapas bar doing patatas bravas and chorizo al vino.
Uppingham is small enough to shop on foot. Nelsons is one of two traditional butchers in the town. Baines is the bakery, and Hambleton Bakery breads are stocked locally too. The Rutland Bookshop has been family-run from 13 High Street West since 1979, dealing in English literature, general fiction and children's books. Topset makes bespoke jewellery by hand. On Fridays a market fills the square from eight until four, keeping up a tradition that goes back to a charter of 1281; the same square hosts the Fatstock Show each November, with livestock penned temporarily in the streets, and a community Feast Day in June.
The town stands on a high ridge, its name meaning the homestead of the upland people. The buildings are honey-coloured ironstone and limestone, packed tight around the Market Place, with open countryside around the town. The Church of St Peter and St Paul stands on the south side of the square, mostly fourteenth-century and heavily restored in 1861 by Henry Parsons of London, still holding fragments of late Saxon sculpture from an earlier church on the site.
Everything else in Uppingham bends around the school. Founded in 1584 by Robert Johnson, Archdeacon of Leicester, it was turned into a leading public school by the Victorian headmaster Edward Thring, began admitting girls in 1975, and counts Stephen Fry and Rick Stein among its old boys. The original 1584 schoolroom survives in the churchyard, Grade I listed and the oldest school building in the town.
Oakham station is about six miles north on the Birmingham–Peterborough line, and the A47's bypass runs along the town's northern edge, with buses to Oakham, Corby, Leicester and Stamford. Rutland Water lies six miles north for sailing, cycling and ospreys in season. To the south-west, Eyebrook Reservoir was where Guy Gibson's 617 Squadron made their final low-level practice runs before the May 1943 raid on the Ruhr dams.
In 2022 The Times named Uppingham the best place to live in the Midlands. On a Friday morning, with the stalls out, it is easy enough to see why.