Chesterfield is a historic market town in Derbyshire know for its crooked spire. It is built over a Roman site which is also on top of an Iron Age fort. The Romans probably settled here because the area is so rich in natural minerals like coal, lead and tin. In Domesday, the town was known as Cestrefeld meaning open field, and its early prosperity was largely a result of its role as a market town, which served the whole of the north east of Derbyshire. The town received its market charter in the year 1204 from King John and around two hundred and fifty stalls can still be found in the town centre every Monday, Friday and Saturday. A flea market takes place each Thursday.

Chesterfield benefited greatly from the building of the Chesterfield Line part of the Derby to Leeds railway North Midland Line, which was begun in 1837 by George Stephenson. During its construction, a sizeable seam of coal was discovered during the construction of the Clay Cross Tunnel. This and the local ironstone were promptly exploited by Stephenson who set up a company in Clay Cross to trade in the minerals. During his time in Chesterfield, Stephenson lived at Tapton House, and remained there until his death in 1848. He is buried in Trinity Church. In 2006, a statue of Stephenson was erected outside Chesterfield railway station.

The peaceful Queen's park has been the focus of much of Chesterfields leisure since Victorian times. It provides a boating lake, gardens, childrens play area and is occasionally used for county cricket matches. There is also a modern sports centre, providing facilities for squash, badminton, swimming, tennis and other sports.

The Town centre of Chesterfield has retained much of its pre-war era layout. Chesterfield is home to one of the largest open air markets in Britain, the stalls sitting either side of the historic Market Hall. In the middle of town, a collection of narrow medieval streets make up "The Shambles", which houses The Royal Oak, one of Britain's oldest pubs.

The Chesterfield Canal linked the town to the national network of waterways, and was the most important trade route through the 19th century. Overtaken by rail and then road for freight transport it fell into disuse, but has been partially restored since the mid-20th century for leisure use. However, the section through Chesterfield remains isolated from the rest of the waterway network.

Chesterfield is perhaps best known for the "Crooked Spire" of its Church of Saint Mary and All Saints and is why the local football team is known as The Spireites.