There is considerable evidence that roundabouts are the safest and most efficient form of traffic control for most intersections. The potential use of roundabouts with all their inherent benefits may be greatly diminished if they are not able to accommodate oversize/overweight (OSOW) vehicles, sometimes called “Superloads.” The problem, therefore, is how to accommodate OSOW vehicles without sacrificing the integrity, safety and other benefits of roundabouts. This study uses TORUS software to design six standard roundabouts using guidance from the latest Federal Highway Administration (FHWA) roundabout guide. Six OSOW check vehicles from the Wisconsin Department of Transportation’s library were used to modify the designs to accommodate these selected check vehicles at the roundabouts. These six OSOW check vehicles were used to conduct swept path analysis using AutoTURN software at the selected six standard roundabouts for right turn, through, and left turn simulations. The space requirements for these maneuvers were analyzed in detail. Various strategies for better accommodating these OSOW check vehicles were suggested and experimented with in this study using AutoTURN software simulations. The effectiveness of using a straight passage through the center island for OSOW vehicles was also addressed in this study and was found to be effective. All the strategies investigated in this study proved to be effective in accommodating OSOW vehicles when compared to conventional ways of using a roundabout. The needed total truck apron was calculated and used as a reference to determine an effective strategy for accommodating OSOW vehicles. This research can be used as guidance for transportation engineers, planners and decision makers to determine possible ways of designing a roundabout at an intersection where certain OSOW vehicles are expected.