Route 66 zigzagged southwest across Madison County, Illinois, before crossing the Mississippi River into Missouri. Various alignments of this segment of the "Mother Road" rolled through pastoral farmland, headed down main streets, and later straightened as it bypassed towns. From 1926 to 1977, the path of the highway changed numerous times and crossed the Mississippi River on no less than five different bridges. Along the way motorists watched for the blue neon cross on St. Paul's Lutheran Church to guide their nighttime travel; they counted on the doors of the Tourist Haven, Cathcart's, or the Luna Cafe to be open for business. Travelers crossed their fingers that they wouldn't get stuck at the bend of the Chain of Rocks Bridge and hoped they could make it up Mooney Hill in the winter. A later alignment took motorists right by Fairmount Park and Monks Mound

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