Traffic engineers are responsible for designing the optimum pedestrian tracks at every new or retrofitting intersection project. The intent is to deliver a safe crossing track with minimal interference with the traffic flow at signalized and un-signalized intersections with and without traffic lights and at midblock crosswalks. Most current practices are to select a crosswalk based on similarities at other intersections with some modifications. Municipalities face challenges in choosing the optimum pedestrian crosswalk at locations with an increased number of lanes, the existence of raised medians near a roundabout, or when the speed is greater than 70 km/h. Accordingly, it is necessary to develop a practical and effective approach for planning engineers allowing them to select a proper crosswalk at such locations to avoid fatalities. In addition, there should be real-time monitoring of crosswalks to make any necessary modifications. This can be accomplished by installing intelligent monitoring systems that collect real-time data and transmit them to a controlling unit for processing and recommending effective proactive measures before it is late. Such functionality is becoming feasible nowadays with the recent advances in the Internet of Things (IoT) technology and the revolution in sensor technology, wireless communication, and data-treating algorithms. This paper provides background on the current practices and critical concerns and a valuable framework for integrating intelligent technologies with the aid of IoT technology to arrive at safe and effective crosswalks with reduced conflict meddling with the traffic flow.