Abstract: A steerable wheeled device such as an in-line skate or roller ski has a hollow or dish-shaped wheel, a wheel bearing, and a wheel support connecting the wheel to a steering structure that extending substantially within the outer radius of the wheel, and steers as the user's weight is displaced. The device preferably has a side-mounted chassis, and oversize wheel positioned in front and in back of the user's foot. The chassis may contain a damping and centering force mechanism to moderate behavior of the steering or suspension. Brakes such as drum or disk brakes are connected to one or more wheels and preferably actuated, e.g., with a boot-actuated linkage, such that braking occurs upon the user adopting a specific posture. In a preferred construction, the stance shifts weight back and/or down so that deceleration does not occur until the user has assumed a stable stance.