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.
29. The Hollingwood, Private Drive, Hollingwood
A local example of the more elaborate inter-war pub construction which was popular with breweries and the public during the 1920s/30s. Characterised by subtle arts and crafts influences, including leaded light windows, bell tower and central stone 2-storey bay. Photo: Google
30. Victoria Inn, Victoria Street West, Brampton, Chesterfield
Victorian pub constructed of brick, with render (1st storey) and slate roof. It has an attractive front elevation with Dutch style gables, a canopy over the door and windows and leaded light windows. Of note are the art-nouveau influenced stained glass windows on ground floor which were likely added in Edwardian times. Photo: Google
31. The Victoria, Lowgates, Staveley
Large Victorian inn constructed at the same time as the residential development on adjacent Wateringbury Grove in the 1890s. Given the location of the former Staveley Town Station on Lowgates it is likely that the pub would have been aimed at passengers using the local railway. The building is constructed in red brick and has pitched slate roofs. It is notable for areas of well-crafted decorative brickwork and original sash windows. Notwithstanding some unsympathetic changes, has remained relatively unspoilt. Photo: Google
32. The Royal Oak, The Shambles, Chesterfield
The Royal Oak, in the Shambles, is the town's oldest pub and is Grade II listed. With origins dating back to the 16th century or earlier. Situated in a medieval, timber-framed, Grade II* listed building, it represents a crucial piece of local history. Documented as an inn from 1722 it consists of two buildings of differing period and character; the older top bar dating to the sixteenth century. Recently acquired and refurbished by Meg Hartman and Patrick Hopkins in April 2025. Photo: Brian Eyre