Chesterfield is an ancient market town lying at the crossroads of England, the hub of trade routes from all points of the compass; there is evidence of both Saxon and Roman settlements on its site. Recorded in the Domesday Book of 1086, there are hints of Chesterfield's medieval past in the names of the town-centre streets, such as Knifesmithgate, Saltergate and Glumangate - the latter refers to a gluman or gleeman who was a minstrel.
Life in Chesterfield has revolved around its market since the town's earliest days, and was earning Royal revenue in 1165 as the Sheriff of Derbyshire recorded in the Pipe Rolls; the market earned the princely sum of £1.2s.7p for the Crown that year. The Pipe Roll of 1182 mentions a fair in Chesterfield; these were large markets lasting for several days and drew traders and buyers from far afield. The town was granted a formal charter in 1204, making it the first of eight free boroughs in the country. A few historic buildings remain including a fine 18th century terrace lining Saltergate, and in the Shambles the Royal Oak Inn has survived from Tudor times. The Victorian Market Hall, built in 1857, overlooks the cobbled Market Place.
Chesterfield's parish church of St Mary and All Saints is the town's most notable landmark. Its twisted spire, leaning out over the surrounding rooftops, is 9ft 4ins out of line, and can be seen for miles about; the central tower and spire were built in the 14th century. Local folklore has it that the builders intended the 228ft high spire to be built with a twist in it. However, it is more likely that the spire, made of unseasoned wood and covered with heavy lead plates, warped when the heat of the sun expanded the plates, resulting in its distorted shape. Thus it has remained for some 200 years. The spire is eight-sided, but the herringbone pattern of the lead slates, trick the eye into seeing sixteen sides from ground level.
The Cock and Pynot (dialect word for magpie) Inn at Old Whittington, on the north side of Chesterfield, is now called the Revolution House. Three local noblemen, including the 4th Earl of Derbyshire, met here to plan their part in the eventual overthrow of the unpopular Catholic King James II, in favour of his daughter Mary and her husband William of Orange. The Glorious Revolution took place later in the same year, November 1688; Revolution House is now a museum open to the public.Railway pioneer George Stephenson moved to Chesterfield in 1837, eight years after his steam locomotive ‘Rocket' had revolutionised railway transport. He married the daughter of a local farmer and resided at Tapton House until his death in 1845. He is buried in the chancel of Chesterfield's Holy Trinity Church, and his name lives on in Stephenson Memorial Hall, now a museum.
Lying south of Chesterfield is Hardwick Hall, built at the end of the 16th century by Elizabeth, Countess of Shrewsbury, ancestress of the Dukes of Devonshire. Her initials E.S., Elizabeth Shrewsbury, still stand in huge letters on top of the towers which front the Hall. Inside are fine Elizabethan furniture, tapestries and portraits; outside is an Elizabethan enclosed garden.
To the east of Chesterfield is Bolsover Castle, the remains of a 17th century mansion built on the site of a Norman castle, rising high above the countryside, perched on a craggy mound. The Riding School, also 17th century in origin, remains in use.