An anti-winding assembly reduces or prevents debris from winding on a trimmer and/or makes them easier to remove. The trimmer includes a trimmer head mounted to a rotatable arbor and supporting one or more cutting lines. The anti-winding assembly includes a bearing positionable between the trimmer head and an adjacent trimmer component. The bearing includes a freely rotating outer race. A shield positioned radially outward of the bearing adjacent the outer race shields gaps between the bearing and the trimmer head and between the bearing and the adjacent trimmer component. The anti-winding assembly prevents trimmed debris from being wound up near the trimmer head.