The Grainstore Brewery brews its own beer inside a former grain store beside Oakham railway station, and has done since September 1994. Wednesday is pie and pint night. The Good Pub Guide has named it Own Brew Pub of the Year four times, and the evenings run to jazz, blues and rock, with darts, bar billiards and giant Jenga for anyone not there for the music.
The rest of the pubs cluster around the Market Place and High Street. The Lord Nelson sits directly opposite All Saints' Church, pouring Everards beers in a room with plenty of olde-world character. The Admiral Hornblower, on the High Street, is a 17th-century former farmhouse that kept most of its bones when it became a hotel and restaurant. The Wheatsheaf, another Everards house, has a well-regarded beer garden and pours a good range of ciders alongside the ale. The Buttercross keeps a small adventure playground beside its outdoor seating, which is useful with children.
For food to take back, Nelson's Butchers is at 26 High Street. Northfield Farm Shop, over at Cold Overton, has specialised in rare-breed meat for more than twenty years and brings it to Oakham's Saturday market; Hambleton Farms runs a butchery and deli counter inside Gates Garden Centre. The general market fills the town on Wednesdays and Saturdays, and on the third Saturday of the month a farmers' market lines Gaol Street with artisan bread, cheeses, meats, cakes and vegetables. The independent shops gather on Mill Street, Gaol Street and Church Street.
In the Market Place stands the Buttercross itself, an old covered market cross with the town stocks still fixed beneath it. Above everything is the spire of All Saints', a Grade I church whose nave columns carry carved capitals worth stopping under: animals, birds, foliage, Adam and Eve, a Green Man, and a scene of a fox making off with geese.
Oakham Castle's Great Hall was built in the 1180s and is England's most complete surviving Norman hall, and its walls hold more than 230 horseshoes. Every peer of the realm visiting for the first time must present one to the lord of the manor; the oldest still hanging was given by Edward IV in 1470, and the Duchess of Cornwall added hers in 2014. It is free to walk in and look up.
Titus Oates, who invented the Popish Plot and earned the title "the biggest liar in Christendom," was born here to ribbon-weavers. Sir Jeffrey Hudson, the court dwarf, was baptised here; at about seven years old and eighteen inches tall, he was presented to Queen Henrietta Maria by rising out of a pie in a miniature suit of armour.
The Viking Way finishes here, 147 miles after leaving the Humber Bridge near Barton-upon-Humber; its final stretch follows the shore of Rutland Water and joins the reservoir perimeter track at Whitwell. The station sits roughly halfway between Leicester and Peterborough. Cutts Close Park, laid out over what were once the castle's ponds, has swings and a skatepark.