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Headway is the forward movement of a ship or boat, especially when this is slow or difficult. So the name may have been an inside joke on the part of the Locksmeade estate developers who laid this road out between 1981 and 1982. The estate also includes other streets named after allusions to the nearby River Thames: Anglers Close, Fisherman Close, Locksmeade Road, Thamesgate Close, and Tideway Close