The name Coolsingel comes from the Cool craftsmanship (an area with a feudal form of government dating back to the Middle Ages, with a 'gentleman' as central person).
In 1596, the city bought the Cool, Blommersdijk and Beukelsdijk craftsmanship from Squire Jacob van Almonde.
By Royal Decree of 20 September 1809, the craftsmanship Beukelsdijk, Oost- en West-Blommersdijk, called Cool, was elevated to an independent municipality.
In 1480 there is already a canal on the craftsmanship side opposite the fortification behind Bulgersteyn; the southern part was given the name Schiedamsesingel, the northern Coolsingel, after the major urban expansion around 1500.
The Coolvest was completely filled in in connection with the construction of a wide road in the years 1913-1922 and was then given the name Coolsingel.