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Add in an early dating conversation with my now husband where we dreamed up a Route 66 road trip covering the full span from Chicago to Los Angeles, there was no way I was honeymooning anywhere else. Consider this your battle-tested 2 week Route 66 road trip itinerary! Over the course of the 20th century, it played pivotal roles in westward migration following the Dust Bowl, mobilization during World War II, and the postwar boom of tourism when cross country road trips became the ultimate dream for classic family vacations.
Driving Route 66 has never been about getting from point A to point B. All those cliches about the journey mattering more than the destination? The Mother Road rules at this! Some sections of the original Route 66 have been preserved and even when you do have to take slightly different driving directions, you can still piece together attractions and landmarks that celebrate the essence and nostalgic charm of Route My 2 week Route 66 road trip took place in late May and early June and this was a great time of year.
Temperatures are warm, but there are relatively fewer mega hot days, and we beat schools being out of session so destinations were not crowded with vacationing families. I would wager a guess though that the actual best time to visit Route 66 is in the fall. In October, you would get a little fall foliage in the Midwest and a chance to plan your trip around the International Balloon Fiesta in Albuquerque.
Yeah, you really, really do. While you could technically drive Route 66 in a shorter period, you would hardly have time for anything but driving. I think the ideal length for a Route 66 road trip would be a month. There were still lots of stops we missed out on and, with only one exception, we never spent more than one night in a single city. As is, a 2 week Route 66 road trip itinerary is just enough to experience the whole road from tip to tail and get an introduction to everything it has to offer.
Navigating Route 66 can be a bit of an adventure in itself, since a lot of the original highway has been replaced by the interstate system or simply fallen into disrepair after its decommission.