A side-mount mowing attachment for a riding mower or yard tractor is removably secured to the riding mower by single hinge pin, allowing the side-mount mowing attachment to articulate and follow the ground contour independently from the primary mowing deck of the riding mower when in a lowered and operational configuration, and which may to be secured in an upright and vertical position when not in use. Power is provided to the cutting assemblies of the side-mount mowing attachment by a drive-belt and pulley assembly coupled to the primary mowing deck drive mechanism. A winch assembly facilitates lifting of the side-mount mowing attachment to the raised and upright position when not in use. When moved to the raised and upright position, tension is automatically released on the drive-belt in the belt and pulley assembly, thereby stopping the transfer of power from the primary mowing deck drive mechanism to the side-mount mowing attachment cutting assemblies.