Route 66 was established on November 11, 1926, ran from Chicago to Santa Monica, and was decommissioned as a federal highway in 1985. 2026 was the road's centennial year: Congress passed the Route 66 Centennial Commission Act in 2020, and states and towns organized events and maps around it (the official centennial site lists them). Event dates change, but the road itself stays the same, and the plan on this page works in any year.
The first thing to know is that much of the old road is now replaced by interstates: I-55 from Chicago to St. Louis, I-44 through Missouri and Oklahoma, I-40 from Oklahoma to Barstow and I-15 and I-10 at the California end. You do not drive one road; you drive the historic alignments that still exist, often within sight of the interstate that took its traffic. The National Park Service puts the route at about 2,400 miles (3,860 km) counting every alignment. The line this page uses, the signed Historic US 66 chained into one path, is 2,260 miles (3,637 km), so expect your odometer to read more.
Twelve days means eleven nights, each in a real Route 66 town: Springfield, Rolla, Joplin, Oklahoma City, Shamrock, Tucumcari, Albuquerque, Gallup, Flagstaff, Kingman and Barstow. The twelfth day ends in Santa Monica. There is no official day-by-day itinerary, so the distances are measured along the road line, not copied from a source, and the stops are the towns on the line that make a sensible night.
Be honest with yourself about the pace. The days run from 139 to 242 miles (223 to 389 km), they average about 188 miles (303 km), and four of them pass 200 miles (322 km): Springfield to Rolla, Joplin to Oklahoma City, Shamrock to Tucumcari and Kingman to Barstow. Those are driving days with short stops, not days for museums. If you want time on the ground, add two days and split the Oklahoma City day at Tulsa, about halfway, and the Mojave day with a night in Needles; that is this page's suggestion, since the sources give no official slower itinerary. The decision that matters most is the time of year, because Mojave heat and highland winter are the two ways this trip goes wrong.