NCN route 67 comes into Chesterfield from the north either along the Chesterfield Canal towpath (also the Trans Pennine Trail) or the more hilly option via Inkersal and Brimington Common.
Currently route 67 finishes at Chesterfield railway station but parts of it leading to Long Eaton are in place. Officially it can be picked up again at Norbriggs on the Five Pits Trail, however there is a mainly off road route from Chesterfield railway station to route 67 at Grassmoor Country Park by using the station link, Derby Road shared path, Rother Washlands path (currently closed) and through the Avenue site. This should eventually be route 67 but because of surfacing issues and badly installed barriers it won’t be adopted in the foreseeable future.
Going west, if the Hipper Valley Trail is eventually extended to Holymoorside it is planned to link Chesterfield railway station to the Monsal Trail (route 680) using an on road route up ‘Cathole’ and across Beeley Moor. Note that an extension of route 680 from Rowsley to Matlock is already built.
Going East there have been vague plans to link up to route 648 in Shirebrook via Bolsover but with the opening of the Poolsbrook to Creswell route it is possible to get to Shirebrook almost traffic free using the Archeological Way.
Link to the Sustrans mapping site here.
The map below shows the routes around Chesterfield, the purple line south of Chesterfield shows the link route which is now open:
An overall map of National Cycle Routes: