Oakham is a market town and civil parish serving as the county town of Rutland, which is England's smallest county. Located in the East Midlands region of the United Kingdom, it sits to the west of Rutland Water within the Vale of Catmose. The town occupies a strategic position 25 miles east of Leicester, 28 miles southeast of Nottingham, and 23 miles northwest of Peterborough. Its elevation ranges from 325 to 400 feet above sea level, providing a distinct geographical setting for this historic settlement.

The town's name derives from the homestead or village of Oc(c)a, reflecting its early origins as an ancient parish. Oakham gave its name to the Oakham Hundred, one of the five historic hundreds of Rutland. Administrative structures evolved significantly over centuries, including the creation of a parish council under the Local Government Act 1894 and the establishment of an urban district council in 1911. Following the abolition of the urban district in 1974, the current Oakham Town Council was established to manage local governance alongside Rutland County Council.

The town is defined by its Norman heritage and architectural landmarks, most notably Oakham Castle, whose great hall dates from approximately 1180–1190. This Grade I listed building is the earliest surviving complete hall of any English castle and features Romanesque details including carvings of musicians. All Saints' Church, with its 14th-century spire restored by Sir George Gilbert Scott, dominates distant views. The historic market place contains a Grade I listed Buttercross with an octagonal stone-slate roof and wooden stocks.

Oakham attracts visitors through unique traditions such as the hanging of ceremonial horseshoes in the castle hall, a custom enforced for over 500 years when royalty or peers visit. The town hosts an open-air market every Wednesday and Saturday near the ancient Buttercross. Cultural attractions include the Rutland County Museum, housed in the old Riding School of the Rutland Fencible Cavalry, and a statue of Queen Elizabeth II unveiled in 2024. These features, combined with its status as a county town, draw significant tourist interest.

Oakham had a population of 11,267 as of 2021, though earlier records cite 12,149 in the 2021 census and 11,000 in 2011. The economy benefits from tourism and local services, with education provided by institutions like Oakham School and Catmose College. Transport links include Oakham railway station on the Birmingham–Peterborough line served by CrossCountry and East Midlands Railway. Most bus services are operated by Centrebus and Blands, connecting the town to nearby communities such as Corby and Stamford.