Chesterfield is a market town and a borough in Derbyshire, England. It lies 24 miles (39 km) north of Derby and 11 miles (18 km) south of Sheffield, at the confluence of the rivers Rother and Hipper. The borough – which includes the settlements of Whittington, Brimington and Staveley – had a population of 103,800 in 2011. Chesterfield is the second largest town in the ceremonial county of Derbyshire, after the city of Derby.

Archaeological examination of the town has traced its beginnings to the 1st century AD and the construction of a Roman fort, which became redundant and was abandoned once peace was achieved. Later an Anglo-Saxon village grew up on the site. The name Chesterfield derives from the Anglo-Saxon words caester (a Roman fort) and feld (grazing land).

Chesterfield received its market charter in 1204. It still has a moderately sized market of about 250 stalls held three days a week. The town sits on a large coalfield, which formed a major part of the area's economy until the 1980s. Little visual evidence of the mining remains today.

The town's best known landmark is the Church of St Mary and All Saints, popularly known for its "crooked spire", which was originally constructed in the 14th century.

Chesterfield was in the Hundred of Scarsdale. The town received its market charter in 1204 from King John. The charter constituted the town as a free borough, granting the burgesses of Chesterfield the same privileges as those of Nottingham and Derby. In 1266, it was the site of the Battle of Chesterfield, in which a band of rebel barons were defeated by a royalist army.

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