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Oakham is a market town and civil parish in Rutland in the East Midlands of England of which it is the county town. The town is located 25 miles (40.2 km) east of Leicester, 28 miles (45.1 km) south-east of Nottingham and 23 miles (37.0 km) north west of Peterborough. It had a population of 12,149 in the 2021 census. Oakham is to the west of Rutland Water and in the Vale of Catmose. Its height above sea level ranges from 325 to 400 ft (99 to 122 m).

Oakham railway station serves the county town of Oakham in Rutland, England. The station is situated almost halfway between Leicester – 27 miles (43 km) to the west – and Peterborough – 25 miles (40 km) eastward on the (as built) Syston and Peterborough Railway, the line is the Birmingham to Peterborough Line. Oakham is the only surviving passenger railway station in Rutland. The line is served by CrossCountry services between Birmingham New Street and Stansted Airport or Cambridge. There is also an infrequent East Midlands Railway service to London St Pancras.

All Saints' Church, Oakham is a parish church in the Church of England in Oakham, Rutland. It is Grade I listed.

The Market Cross in Oakham, Rutland, England, is a market cross dating from the 16th or 17th century. Market crosses, also termed butter crosses, may derive from the high crosses or free-standing stones of the Early Mediaeval period. In the Middle Ages they were often used as gathering points in the centres of communities, generally as venues for regular markets. Beneath the cross is a set of stocks. Both are Grade I listed structures and the group forms a Scheduled monument.

Oakham School is a public school (English fee-charging boarding and day school) in Oakham, Rutland, England. The school was founded in 1584 by Archdeacon Robert Johnson, along with Uppingham School, a few miles away. They share a common badge design (and a strong rivalry), but while Uppingham's colours tend towards blue and white, Oakham's are black and red. Under headmaster John Buchanan, in 1971 Oakham was the first boys' independent secondary school in Britain to accept both male and female pupils throughout the whole school and not just in the sixth form. In 1995, it was the first public school to go on-line.Leicestershire County Cricket Club occasionally plays games on the school grounds.

Harington School is a free school sixth form located in Oakham in the English county of Rutland. The school is named after John Harington, 1st Baron Harington of Exton and John Harington, 2nd Baron Harington of Exton, two notable peers in Rutland in the late sixteenth and early seventeenth centuries.Established in September 2015, Harington School is governed by a trust which is overseen by three secondary schools located in Rutland: Uppingham Community College, Oakham School and Catmose College. Harington School has its own new dedicated building located next to Catmose College.

Oakham School is a cricket ground in Oakham, Rutland. Forming part of sports facilities of Oakham School, the ground dates from around 1821. First-class cricket was first played at Oakham School in the 1935 County Championship, with Leicestershire playing against Kent. Leicestershire used the ground as an outground on three more occasions prior to the Second World War. Following a gap of 62 years, first-class cricket returned to Oakham School in 2000, when Leicestershire played the 1999 County Champions Surrey. The ground has since been used intermittently as an outground for first-class matches by Leicestershire, with five matches played there since 2000. During the first decade of the 2000s, Leicestershire played nine List A one-day matches at the ground between 2001–08, before returning after a ten year gap when they played Lancashire in the 2018 Royal London One-Day Cup. In 2020, Leicestershire announced plans to revive the Oakham Cricket Festival and make it a permanent part of Leicestershire's county schedule.

Oakham Castle is a historic building in Oakham, Rutland. The castle is known for its collection of massive horseshoes and is also recognised as one of the best examples of domestic Norman architecture in England. It is a Grade I listed building. Owned and managed by the Rutland County Council, Oakham Castle is licensed for civil ceremonies. Admission to the castle is free.

Rutland County College was a post-16 (or sixth-form) college, based mainly in Oakham, Rutland, England. In September 2012 it opened on a new site in Barleythorpe on the outskirts of Oakham. However, the college was meant to move to its main campus in Casterton. The new Sixth Form was going to be renamed CCR6 and would have opened in September 2017. In September 2016, however, the college announced closure of its Year 12 provision for that year, because of low numbers of students applying to it. In June 2017 the remaining provision was also closed and the college ceased to operate.Previously called Rutland Sixth Form College, it was built on the site of the historic girls' grammar school for Rutland, originally known as Rutland High School for Girls. It was incorporated into Tresham College in August 2000, changing its name to Rutland College. In 2009 Tresham Institute announced its intention to withdraw from Oakham. Tresham sold the existing buildings and land, leaving the local community to find a new site and the capital to build a new 16-19 college. In autumn 2009 Rutland County Council announced that Casterton Business and Enterprise College (an 11-16 community college) would take responsibility, in partnership with the County Council and Tresham, for managing the college and would provide 100 sixth form places at its Great Casterton site in addition to Oakham. The second phase of the proposal included moving to a new site and in November 2010 it was announced that the College would relocate to occupy the former EEF Conference Centre in Barleythorpe in September 2012.The College prospectus described a new post-16 programme with a range of courses including ‘A Level’ subjects, the new 14-19 diplomas, apprenticeships, or career specific ‘vocational’ training.The College was judged Outstanding by Ofsted in November 2010, although in November 2014 the College was judged to 'require improvement'. Former and participating students formed the 'Hand-stitched Theatre Company' who were rated four stars at the Edinburgh Fringe Festival.

Rutland County Museum is located in Oakham, Rutland, in the old Riding School of the Rutland Fencible Cavalry which was built in 1794–95. The museum, opened in 1969, houses a collection of objects relating to local rural and agricultural life, social history and archaeology. Temporary exhibitions are shown alongside the permanent displays. Admission to the museum is free.

Catmose House is a municipal facility in Catmose Street in Oakham, Rutland, England. The house, which is the headquarters of Rutland County Council, is a Grade II listed building.

The Oakham Canal ran from Oakham, Rutland to Melton Mowbray, Leicestershire in the East Midlands of England. It opened in 1802, but it was never a financial success, and it suffered from the lack of an adequate water supply. It closed after 45 years, when it was bought by the Midland Railway to allow the Syston and Peterborough Railway to be built, partly along its course. Most of it is infilled, although much of its route can still be seen in the landscape, and there are short sections which still hold water.