Opened in 1777, the Chesterfield Canal once linked Chesterfield with the tidal River Trent at West Stockwith. Engineers James Brindley and John Varley commenced work on the canal which included the 2884 yard (2637m) long Norwood Tunnel, which was slightly longer than Brindley's tunnel at Harecastle on the Trent & Mersey Canal. James Brindley did not live to see these canals and tunnels completed, dying in 1772. John Varley continued work on the Chesterfield Canal and it was completed in little over five years. At 46 miles (74km) long it was a successful canal, paying dividends from 1789 until the coming of the railways.
Known locally as "The Cuckoo Dyke", the canal carried coal, iron, lead, wheat, timber and local merchandise in and out of Derbyshire. Stone for the Palace of Westminster was also transported via the canal having been quarried at North Anson near Rotherham.
Norwood Tunnel unfortunately suffered from subsidence and in 1907 a serious collapse cut the far end of the canal off from the rest of the system. Commercial carrying contined on the canal between Worksop and West Stockwith until the 1950's. Closed in 1961, the canal fell into disrepair above Worksop but much of it was saved for pleasure users. Since then the canal has been restored as far as the eastern portal of Norwood Tunnel at Kiveton Park and some of the isolated section from Chesterfield to Staveley has also been brought back into use. Full restoration of Norwood Tunnel is out of the question as part of the western end was infilled to enable the construction of the M1 Motorway over it in the 1960's but there is a proposal to use a short section of the eastern end as it will be possible to build a new canal over Kiveton Park using locks.
Boats of up to 72' by 14' (21.95m x 4.30m) can use the canal from West Stockwith to Retford after which only narrow beam boats of up to 7' (2.13m) wide can cruise up to Norwood. Features on the canal include Drakeholes Tunnel and the Hollingwood Common Tunnel, a disused navigable mine adit near Staveley.