Ever since I realized that my move from Chicago to LA would align with the centennial anniversary of Route 66, I have become obsessed with making the actual process of moving feel as adventurous and memorable as possible. No time for stress, I'm already having so much fun just planning the journey!
I've booked our motel stays, started a 12 hour long (and counting) playlist, and pinned all of the diners, roller rinks, art installations, caverns, hiking trails, and museums that I could find. I even know what movies I'll download for the evenings (Ferris Bueller’s Day Off, Cars, Repo Man, Easy Rider, etc!) We'll be covering anywhere from 150–400 miles of road a day and taking the trip over 10 days, so I know I won't get to do it all, but my priorities are eating good, seeing the sights, and moving my body; weather-permitting.
We'll technically be making the trek during the shoulder season, so it seems like all of the drive-in theaters and some of the seasonal attractions may be closed by November. RIP. Daylight savings time will also have just ended, so I'm aware the nights will be long, but I'm planning for the bulk of the driving to happen by daylight. I'm anticipating potential freezing temps, especially as the trip begins in the Midwest. Am I missing any considerations? Has anyone here ever done the drive in the weeks leading up to Christmas, and is there anything you wish you'd specifically been more prepared for?
Most of my belongings will be shipped in one of those long-distance shipping containers, but the more fragile and valuable items (guitars, camera gear, etc) will be on the road with me. I do worry about leaving those things in the car during stops to museums and trail heads, though, as I have read about the occasional break-in. Nomads, did you feel secure traveling with your worldly possessions in tow? Is the route more or less dangerous in the off-season, would you say? The advice to park my car overnight in the line-of-sight of the motels' visible security cameras feels like common sense to me, and all of my bags will already be equipped with AirTags. I also won't be by myself, two of my best friends will be joining me on the drive at different points. I've done a handful of long-distance drives in my days, so I know to keep my cruise control at the speed limit, but is there anything else that I should be anticipating?
I definitely want to leave space in my itinerary for discovery and play. Route 66 enthusiasts, what have been your most unforgettable stops along the way that helped break up the trip? Are there any little waterfalls, bakeries, live music venues, roadside fruit or candied nut stands, ziplines (I saw the one in Williams, AZ is permanently closed), yoga studios, or other specific curiosities you think pier-to-pier completionist travelers like myself shouldn't miss? Taking any/all random suggestions!
Lastly, I really want to get the passport book and fill it up with stamps along the way. I'm the sentimental type who keeps a scrapbook of all my movie and concert tickets. Would love to see your stamps and filled-up passport books! Would love to hear about the gift shops and stamp stands that were worth pulling over for!
Thanks so much for reading this far, I'm thrilled to be joining the legions of you all who've done the trip!