Devices, methods and systems are provided for delivering a guidewire to a target location within an anatomic structure. In one embodiment, a guidewire includes a guidewire body and a deployable guidewire end portion. The deployable guidewire end portion is coupled to a distal end of the guidewire body, the deployable guidewire end portion having a self-expandable structure moveable between a constricted position and an expanded position. With this arrangement, the guidewire end portion, in the expanded position, includes a distal most side surface sized and configured to a traumatically position and brace the guidewire end portion against tissue at the target location.