Route 66 is part of the U.S. numbered highways system, which is distinct from the interstate highway system. The U.S. numbered highways system is in fact the precursor, and can be treated as the result of the first attempt to formally define a national highway system with uniform markings (previously, these highways were designated/maintained by local private entities). As a result, it did take a bit of trial and error to determine the various routes, and other changes occurred later to better facilitate traffic.
Route 66 started at a time when rods went between towns connecting the business districts. As Henry Ford sold more model Ts traffic became a problem even in small towns, a road was built around the town, then the business moved to the new road, wash rinse repeat. Take a look at Gartner or Litchfield IL. For larger realignments think about advances in bridge and road building tech. Look at Devils Elbow in Missouri. 2 lane 66 is teardrop road and follows the river, 4 lane 66 cuts the corners. In other places there just wasn’t a road, look at Clines Corner in NM. Early 66 veered north from Santa Rosa connecting to the road to Santa Fe and then back south to Albuquerque, eventually the road was built straight west cutting out the Santa Fe loop.
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