A loading and support rack is provided for support from the rear of a pickup truck load bed and with the rack overlying and extending forwardly of the tailgate of the pickup truck when the tailgate is in a horizontal position. A horizontal transverse winch mounting structure is provided for support from the upper marginal edge portion of the forward wall of the truck bed and includes a winch supported from the mid-portion thereof and vertical stakes supported from the opposite ends thereof snugly downwardly receivable in the upwardly opening stake sockets of the side walls of a pickup load bed closely adjacent the forward end of the bed. An elongated support frame is also provided and includes front and rear ends, dependingly supported ground engageable wheels supported from opposite side portions of its rear end, slightly dependingly supported opposite side forward support wheels and a center rear roller as well as opposite side rollers spaced centrally intermediate the opposite ends of the frame. In addition, the forward end of the frame includes an upper horizontal transverse member beneath which the bow of a boat supported from the frame may be received and opposite side portions of the rear end of the tailgate supported rack include rollers along which opposite side longitudinal members of the boat supporting frame may roll with a boat supported thereon, to which boat the free end of the winch cable is attached for pulling the boat as well as the boat supporting frame up onto and in the load bed of the pickup truck.