Building work at the old Cattle Market and other sites has revealed evidence of settlement on the hill since the Bronze Age. Remains of a Roman villa have been found on the east side of Barton Road. Bosworth as an Anglo-Saxon village dates from the 8th century.
Before the Norman Conquest of 1066, there were two manors at Bosworth one belonging to an Anglo-Saxon knight named Fernot, and some sokemen. Following the Norman conquest, as recorded in the Domesday Book of 1086, both the Anglo-Saxon manors and the village were part of the lands awarded by William the Conqueror to the Count of Meulan from Normandy, Robert de Beaumont, 1st Earl of Leicester. Subsequently, the village passed by marriage dowry to the English branch of the French House of Harcourt.
King Edward I gave a royal charter to Sir William Harcourt allowing a market to be held every Wednesday. The village took the name Market Bosworth from 12 May 1285, and on this day became a "town" by common definition. The two oldest buildings in Bosworth, St. Peter's Church and the Red Lion pub, were built during the 14th century.
The Battle of Bosworth took place to south of the town in 1485 as the final battle in the Wars of the Roses between the House of Lancaster and the House of York. Following the discovery of the remains of Richard III in Leicester during 2012, on Sunday 22 March 2015 the king's funeral cortège passed through the town on its way to Leicester Cathedral for his reburial. This event is now commemorated with a floor plaque in front of the war memorial in the town square.
In 1509 the manor passed from the Harcourts to the Grey family.
In 1554, following the beheading of Lady Jane Grey, the manor of Bosworth was among lands confiscated in the name of Mary I of England and her husband Philip II of Spain. They awarded the manor to the Catholic nobleman Edward Hastings. In 1567, his heirs sold it to Sir Wolstan Dixie, Lord Mayor of London, who never lived in Bosworth. The first Dixie to live in Bosworth was his grand-nephew, Sir Wolstan Dixie of Appleby Magna, who moved to the town in 1608. He started construction of a manor house and park, as well as establishing the free Dixie Grammar School. The modern hall, Bosworth Hall, was the work of Sir Beaumont Dixie, 2nd Baronet (1629–1692).
In 1885 the 11th Baronet 'Beau' Dixie was forced to auction Bosworth Hall to pay his gambling debts. It was bought by Lady Agnes Tollemache, whose husband Charles Tollemache Scott enlarged the estate, planted woodlands and rebuilt the lodges and farms. Lady Agnes' daughter sold the estate in 1913.
This includes people born, educated, or having lived in Market Bosworth.
The Town entered into the Britain in Bloom competition on the 500th anniversary of the battle in 1985. Floral decorations were displayed around the town. The success of this entry caused the formation of the "Bosworth in Bloom Committee", to prepare for more displays. In 2012 – the Town reached the national finals for England and won a Gold Award.
The Town has a football team Market Bosworth football club with teams across various age groups from under 5s to over 35s. The triathlon club and cricket club are based at the same ground, the sports and social club.
The facilities within Market Bosworth are very good for a town of its size.
The market square is in the centre of the town, surrounded by various shops, including craft shops, small cafes, a traditional butchers and green grocers store, a bank and estate agents. A regular market takes place on Wednesdays and monthly Sunday Farmers’ Markets.
The town has three schools, Market Bosworth Primary and Junior School, The Market Bosworth School, and the private Dixie Grammar School, three churches, Anglican, Catholic and Free Church, a fire station, and a large hotel.
The town centre boasts many characterful, historic buildings. In the corner of the Market Place are two cottages, known as the Rose and Thistle Cottages, named to confirm the link of the Dixie family to England and Scotland. The properties date back to 1640 (engraved in the frame at first floor) and the original Crook A frame can still be seen in Thistle Cottage which is now a tea room and bistro. Rose Cottage remains as a private residence. The cottages were extensively rebuilt and re-faced with brickwork in 1807 (evidenced by date stamped brick on Thistle Cottage facade) to modernise the appearance in keeping with other properties around the Market Place.
There are three pubs, The Black Horse, The Dixie Arms Hotel and the Red Lion, which is one of Bosworth's oldest buildings. Earlier pubs included King William IV, now converted into private residences; Inn on the Park, demolished to accommodate the Sycamore Way housing estate, and the Wheatsheaf, now a small shopping courtyard.
Market Bosworth Country Park and a water trust and a golf course offer outside recreation. The site of the Battle of Bosworth is just a few miles South of the town. Market Bosworth was previously served by the Ashby and Nuneaton Joint Railway which is now the heritage Battlefield Line Railway and runs at weekends from Shackerstone, via Market Bosworth station to Shenton. The Ashby Canal runs adjacent to the railway and is served by Bosworth Marina with moorings for 150 boats.