This study seeks to find a strategy to capture the most observed trajectories with a minimum number of algorithms. GPS information on 4,538 real trips from 131 travelers in 2008 was collected and analyzed in Minneapolis-St. Paul (the Twin Cities) as part of the I-35W Bridge Collapse study. The high-resolution road network of the Twin Cities includes 108,561 nodes and 277,747 links. Labeling and link penalty approaches are combined to generate alternatives based on either observed or free-flow speed. Overall, with the best 10 labels, on average, 40 unique routes are generated for each origin-destination pair, and around 80% of all observed trips could be captured with an 80% overlap threshold. About 88% of all observed trips have an average deviation within 50 m compared with the best matching result when combining all labels introduced in this study. Freeway-preferred routes cover more observed trips than freeway-avoided routes, and the peak coverage occurs when freeway travel is weighted between 0.8 to 1 of travel on non-freeway links. A random effects panel model is used for predicting the overlap between alternative route and observed trajectory. Multinomial and mixed logit models with a path-size term are applied to model the route selection. These models indicate that alternative routes which are shorter in distance, have faster average free-flow speed, contain a higher freeway percentage, and incur fewer traffic lights, are more likely to have higher overlap with observed trajectories and are more likely to be selected.