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A wind-ing hole (pronounced as in wind = breeze, not as wine-ding) is a wide section of the canal where narrowboats up to 70 feet (21.3 metres) in length, the maximum accommodated by most locks on the canal system, can be turned round.

The Shropshire Union Canal (from Autherley to Nantwich) was engineered by Thomas Telford and opened in 1835. There are long straight sections of this canal which required either embankments or cuttings to avoid the need for locks. Although this was a more difficult procedure, the end route was shorter and the progress for horse drawn working boats could be maintained with (hopefully) no stoppages. The canal (formerly the Birmingham and Liverpool Junction Canal) was opened at a time when railways were making serious inroads into the canal companies' businesses.

The current Shroppie north of Nantwich was formerly the Chester Canal, opened in 1779, and has wider locks and bridges. Boats up to nine feet in beam can still navigate this section; Telford's canal accommodates only narrowboats up to seven feet in beam.