Roads deteriorate at different rates from weathering and use. Hence, transportation agencies must assess the ride quality of a facility regularly to determine its maintenance needs. Existing models to characterize ride quality produce the International Roughness Index (IRI), the prevailing summary of roughness. Nearly all state agencies use Inertial Profilers to produce the IRI. Such heavily instrumented vehicles require trained personnel for their operation and data interpretation. Resource constraints prevent the scaling of these existing methods beyond 4% of the network. This dissertation developed an alternative method to characterize ride quality that uses regular passenger vehicles. Smartphones or connected vehicles provide the onboard sensor data needed to enable the new technique. The new method provides a single index summary of ride quality for all paved and unpaved roads. The new index is directly proportional to the IRI. A new transform integrates sensor data streams from connected vehicles to produce a linear energy density representation of roughness. The ensemble average of indices from different speed ranges converges to a repeatable characterization of roughness. The currently used IRI is undefined at speeds other than 80 km/h. This constraint mischaracterizes roughness experienced at other speeds. The newly proposed transform integrates the average roughness indices from all speed ranges to produce a speed-independent characterization of ride quality. This property avoids spatial wavelength bias, which is a critical deficiency of the IRI. The new method leverages the emergence of connected vehicles to provide continuous characterizations of ride quality for the entire roadway network. This dissertation derived precision bounds of deterioration forecasting for models that could utilize the new index. The results demonstrated continuous performance improvements with additional vehicle participation. With practical traversal volumes, the achievable precision of forecast is within a few days. This work also quantified capabilities of the new transform to localize roadway anomalies that could pose travel hazards. The methods included derivations of the best sensor settings to achieve the desired performances. Several case studies validated the findings. These new techniques have the potential to save agencies millions of dollars annually by enabling predictive maintenance practices for all roadways, worldwide.