The Five Pits Trail is an off-road surfaced route running from Grassmoor to Tibshelf. The Trail is approximately 5.5 miles (8.9km) long, following the route of the former Great Central Railway which served the coal mines of Grassmoor, Williamthorpe (North Wingfield), Holmewood, Pilsley, and Tibshelf. The route can be extended to 7.5miles (12.1km) by continuing through Williamthorpe Ponds nature reserve to Holmewood Woodlands.

The Trail was created by Derbyshire County Council in 1989

Access to the Five Pits Trail is possible via numerous footpaths which cross it, and by a number of roads which cross it. There are car parks provided at several locations: Church Lane in Tibshelf, Station Road in Pilsley, Timber Lane near Astwith, and at both the Birkin Lane and the Mansfield Road entrances to Grassmoor Country Park.