U.S. Route 66 turned 100 years old in 2026, and that's a good enough reason for my first American road trip since 2013! With my good friend Tyler, we flew to Chicago, rented a car, and set out to discover what makes this particular piece of pavement so iconic.

But we're not completionists. We decided before we left that we would go where we felt like going, whether it was technically part of Route 66 or not. So, while we did 'mostly' follow the highway from Chicago to Santa Monica, we did make a few detours and shortcuts in order to hit our favorite spots through the eight states that make up the route, including six National Park sites.

What we found is a little bit of everything that America is: the good (small family-run businesses, funky art, amazing natural beauty), the bad (abuse of Dust Bowl migrants, sundown towns, bypassed ghost towns), the unabashedly cheesy (Uranus, MO, Sid's Soda Ranch, Cadillac Ranch, etc.) and the delicious. Most of all, we found two weeks of fun.

Road trips are a special breed, and Route 66 is the one of the first... and still one of the best ones out there in America. But if you're wanting to do this one (or really, any other one), here are Travelin' Tim's Ten Rules of the Road(trip):

1) Do your research - There is sooooooo much along the 2,278 miles of Route 66. Kitschy statues, funky stores, neon-lit motor lodges, delicious diners, fun and educational museums, natural beauty, and hidden gems. There are also more than a few books, websites and YouTube videos that will tell you all about them. Sample them, and make a list of the Route 66 sites that interest you.

2) Decide what parts of the 'Old 66' roadway you really want to see - Remember that technically, "Route 66" as an official highway doesn't really exist anymore. It's a series of suburban streets, interstate access roads, two-lane country drives, and in some cases, dirt roads that you may or may not want to drive on. While some stretches (notably parts of Illinois south of Joliet, the road from Missouri into a 13-mile corner of Kansas, a beautiful stretch west of Kingman in Arizona, and another stretch through the Mojave Desert in California) are iconic and offer the 'feel' of a Route 66 trip of yesteryear, there are also long stretches that are within a stone's throw of Interstates 55, 44, 40 and 10. Unless you're a completionist (not that there's anything wrong with that), do not feel obligated to drive on every single mile of the old road.

3) Get a navigation guide (NOT Google Maps) - Like I said, 'Old 66' is now a disjointed series of streets, backroads and higways that make it impossible for an app like Google or Apple maps to follow. The Easy 66 Guide for Travelers is the one thing I recommend everyone buy before hitting the road (and no, I don't get a cut of the profits). It has turn-by-turn directions and a guide to literally everything on and off the road. The cost of the book is well worth not experiencing the frustration of getting lost. There are also some apps that are decent, but we found the book to be the most reliable.

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4) Book iconic motels early - Maybe it was because of the 100th Anniversary in 2026, but the Wagon Wheel Motel (Cuba, MO), Boots Court (Carthage, MO), Blue Swallow Motel (Tucumcari, NM), and one of the Wigwam Motels (Holbrook, AZ) were all booked up more than three months in advance of our trip. We did manage to get in a few of the others, but if staying in a classic motel is important to your trip, make those reservations well ahead of time.

 

5) Give it time - I would say that to do Route 66 any justice at all, you need at least ten days, and optimally two weeks (like we did). If you have less than that, plan on just doing a segment (Maybe Chicago-Amarillo, Amarillo to Los Angeles, or St. Louis to Flagstaff). If you've got more time (and money), feel free to add more stops (and diversions) to your trip.

6) Keep an eye on the weather - On a Route 66 trip, you'll be driving from the shore of Lake Michigan through the Ozarks, onto the Southern Great Plains and the high desert to the Pacific Coast. Somehow, we lucked out with near-perfect weather from end-to-end (a cloudy day in Oatman, AZ was the one non-sunny day we had on our trip), but depending on the time of year you're traveling, you could see extreme heat or cold, ice or snow, thunderstorms, flash flooding and (eek) even tornadoes. Keep up with local forecasts and be prepared to adapt your plans to them.

 

7) Don't overplan - On a two-week road trip, things are bound to change. You may get waylaid by traffic or weather, or you may decide you want to spend extra time in one town, or the attraction you really want to see may be closed when you get there, you might find a hidden gem or you may want to detour off the road entirely. Don't be so overscheduled that you can't do any improvising.

 

8) Fuel & Food - Fuel prices in Missouri are way less than they are in Illinois. Likewise, prices in California are far more expensive than they are in Arizona. Also, if you're flying and renting a car like we did, buy a cheap styrofoam cooler and keep snacks and drinks in there for the road.

9) Choose your roadtrip buddy wisely - I can probably count on one hand the number of people I could be stuck in cars and hotel rooms with for two weeks with absolutely no stress - thankfully, Tyler is one of them. It really can make-or-break the entire vibe of the trip. The only drama we had in the ENTIRE two weeks was the ten minutes I thought I'd left my drivers license somewhere (it was on the floor of the car).

 

10) Make the trip yours - Tyler and I sat down a week before we left and asked ourselves 'what do we REALLY want to see, and what are we OK with driving past?' I wanted classic diners, Tyler wanted a few cool bookstores, we both wanted a lot of nature and scenery. We ended up taking in SIX National Park sites (Gateway Arch, Pueblo, Bandalier, Petrified Forest, Grand Canyon and Joshua Tree). On the other hand, the barbed wire museum (McLean, TX) and the Oklahoma City Memorial were among the things we decided we could miss. But your list will likely be entirely different than ours, and that's great. There is no 'right way' or 'wrong way' to do an Epic Route 66 Roadtrip!