A cup holder assembly for a portable and handheld walking apparatus that includes a fastener assembly with an annular clasp operably configured to selectively translate to increase and decrease in diameter an annular recess defined thereon for receiving and retaining a portable and handheld walking apparatus. The cup holder assembly also includes a first hinge member directly coupled to the annular clasp and a second hinge member hingedly coupled to the first hinge member, wherein the second hinge member is operably configured to rotate and have at least one locked position along a rotation path with respect to the annular clasp. The assembly includes a cantilevered support rod with a portion directly coupled to the second hinge member and having a terminal distal end and a cylindrical container member and a container fastener configured to couple with the cantilevered support rod.