A trekking pole assembly includes a trekking pole and a handle assembly mounted to the trekking pole. The handle assembly includes a handle housing with an interior cavity and a shock absorbing member secured within the interior cavity. The handle housing has a top end and a bottom end, an opening defined in the bottom end, and at least one lateral opening. The shock absorbing member is positioned in the handle housing and interposed between the handle housing and the trekking pole. A portion of the shock absorbing member is displaceable through the at least one lateral opening.