Most canal boats are longer than the canal is wide, so special turning points, called “Winding Holes” are needed.
Pronunciation (IPA): WINDING
Winding is pronounced with a short I, as in "windlass", and not with a long I as in "You're winding me up!"
The Old English word for turn is "Windan", also pronounced with a short I (as in windlass, a handle for winding (long I) gears). Since Old English was in use up to and including the 18th century, and since "Canal Mania" is an 18th century phenomenon, it is likely that the change to using the long "i", as in "you're winding me up", occurred about that time. The act of a ship (including sailing ships) turning in a harbour is also called "winding" but is pronounced with a long “i”.
This video shows the Kennet turning around in a winding hole. It's a bit like "Changing direction in the road using forward and reverse gears".
Watch the Kennet, an old Leeds and Liverpool Canal short boat, “winding”
There is a theory that "winding hole" refers to the use of the wind (movement of air) to turn, but it seems unlikely to me as the motive power on canals was a horse -