The Royal Oak in the Shambles, dating to the 17th century, and the distinctive Edwardian Sun Inn being notable examples.
Other historic venues include the Grade 2 listed Spread Eagle and The Portland Hotel, a prominent late Victorian hotel.
The borough has pubs both on the National Heritage List for England as well as the Local List of Heritage Assets drawn up by Chesterfield Borough Council.
33. The Peacock Inn, Low Pavement, Chesterfield
The timber framed building on the site of at least 2 earlier buildings, is Grade II listed. The former public house dates back to the 16th century and features a timber frame on a stone plinth. Photo: google
34. The Spread Eagle, Beetwell Street, Chesterfield
A former coaching inn, the Grade II listed building has retained its character and charm. The late 18th or early 19th-century facade, complete with distinctive arched carriageway. Revitalized in 2025 under new ownership – the team behind the renowned Galleon Restaurant. Photo: Brian Eyre
35. The Rutland Arms, Stephenson Place, Chesterfield
The Rutland was originally the home of Samuel Dutton who was Mayor of Chesterfield between 1818 and 1845. It was purchased after his death in 1848 and opened as the Rutland Hotel in 1860. In 1906 its width was reduced by half to allow the road, which was renamed Stephenson Place, to be widened. The pub was bought at auction in 1921 by Tennants Brewery of Sheffield for £5350. Eventually it became a Whitbread House and traded as a Hogshead Alehouse. The original Hogshead lamps can still be seen above both main entrances. Photo: google
36. The Market Pub, New Square, Chesterfield
The Market Pub is a historic establishment, originally built around 1800 as townhouses before becoming a pub in the 1860s. It was formerly known as the Post Office Vaults (1869) and has held various names over its history, including the Market Hotel. It is a Grade II listed building featuring a 19th-century facade and a WWII-era air raid shelter. Photo: Rachel Atkins