With the pressing need to improve the poorly rated transportation infrastructure, asset managers leverage predictive maintenance strategies to lower the life cycle costs while maximizing or maintaining the performance of highways. Hence, the limitations of prediction models can highly impact prioritizing maintenance tasks and allocating budget. This study aims to investigate the potential of different predictive models in reaching an effective and efficient maintenance plan. This paper reviews the literature on predictive analytics for a set of highway assets. It also highlights the gaps and limitations of the current methodologies, such as subjective assumptions and simplifications applied in deterministic and probabilistic approaches. This article additionally discusses how these shortcomings impact the application and accuracy of the methods, and how advanced predictive analytics can mitigate the challenges. In this review, we discuss how advancements in technologies coupled with ever-increasing computing power are creating opportunities for a paradigm shift in predictive analytics. We also propose new research directions including the application of advanced machine learning to develop extensible and scalable prediction models and leveraging emerging sensing technologies for collecting, storing and analyzing the data. Finally, we addressed future directions of predictive analysis associated with the data-rich era that will potentially help transportation agencies to become information-rich.In classifying highway asset items, it should be noted that state agencies have different classification. For example, California Department of Transportation (CalTrans) categorizes transportation assets in primary classes of pavements, bridges, culverts, and Intelligent Transportation Systems (ITS) [4]. However, North Carolina DOT classifies assets into seven primary groups of pavements, bridges, tunnels, roadside features, pavement markings, rest areas, and maintenance yards [10]. Among these categories, that are different from state to state, we reviewed prediction methods for a subset of assets, including pavements, pavement markings, traffic signs, barriers, and culverts.We focused mostly on recent papers published in the past 20 years. To the best of our knowledge, we included most of the significant research studies reporting the application of predictive analytics. The total number of the investigated papers versus years of publication is shown in Figure 2.