Chesterfield has been a market town since 1165, and the markets remain central to the economy. They're held on the Market Place every Monday, Friday and Saturday, with a flea market on Thursdays as well as regular farmers' markets. The Market Place is in the heart of the town centre, and the streets around it are packed with other shops, pubs and cafes. You'll also find more stores inside the Vicar Lane Shopping Centre.
Just north of the shopping centre is the Chesterfield Visitor Information Centre and the Church of St Mary and All Saints. Better known as the 'Crooked Spire', it has a twisted 14th century spire that defied explanation for many years - local folklore blamed the devil, and historians suggested that the recent Black Death had left the town without skilled craftsmen. Whatever the cause, it's a striking sight, and the views from the tower are fantastic.
You can find out more about the town's history at the Chesterfield Museum and Art Gallery, but if you prefer the great outdoors, Chesterfield couldn't be better placed for exploring the Peak District National Park. You can pick up free walking leaflets from the Visitor Information Centre.