Abstract: Disclosed herein are novel embodiments of progressive mobility aid devices. Such progressive mobility aid devices are designed to progress through a variety of configurations to accommodate the use of the progressive mobility aid device in a safe and secure manner as the user of the progressive mobility aid device traverses a variety of surfaces and terrain such as traversing irregular surfaces including sidewalks and stone-based surfaces; loose surfaces and terrain including gravel and sand; soft surfaces including wet ground and carpeted surfaces; and variable gradient surfaces including stairs and inclining or declining surfaces and terrain. The progressive mobility aid devices accommodate such uses with an articulating design that provides for front legs of the progressive mobility aid device to be pivotably adjusted with respect to the rear legs of the progressive mobility aid device, and with wheel assemblies that are selectively deployable and retractable.