Route 66, and its 2,500 miles, is known affectionately as "The Mother Road." It's the quintessential cross-country road trip experience. From Chicago through the beating heart of America and down to Los Angeles, the route officially ends at the Santa Monica Pier. The road reached peak popularity in the late 40's and early 50's before being officially removed from the US Highway System in 1985. After a few years, travelers from America and beyond started feeling tinges of nostalgia, and by the end of the 1980's it was fast becoming one of the most popular road trip routes once more.
The Illinois stretch of Route 66 is home to some pretty good eats, especially if you like classic American cuisine. Before you hit the road, visit Dell Rhea's Chicken Basket, just outside Chicago, for some of the best fried chicken you'll ever have. They've been serving the home-cooked goodness since 1946.
The Illinois stretch of Route 66 is also home to loads of great roadside attractions, but none shout "retro-kitsch" louder than the massive muffler men statues! The Gemini Giant in Wilmington and Bunyon With a Hotdog in Atlanta, IL are two of the best for photo-ops of this iconic vestige of Americana. While you're in Atlanta, which is a ridiculously charming little town in Illinois, visit the Route 66 Arcade Museum: it's a fantastic hidden gem that features tons of vintage arcade machines you can play.
Illinois is also great for history buffs, as it's home to loads of Abraham Lincoln-inspired attractions, and since the establishment of Route 66, big 'ole statues of "Honest Abe" have been delighting road travelers over the years. For the full Lincoln experience, spend the night at the Pasfield House Inn in Springfield, and just down the road there's the Watermelon Lincoln Monument, and the Railsplitter Covered Wagon in Lincoln.
If quirky roadside attractions are your thing, then you can't get much better than Henry's Rabbit Ranch in Staunton, where you'll find a whole bunch of VW Rabbits all cut in half and sticking out of the ground, like some weird Stonehenge homage. There's also a gift shop and info center on site, and a few actual bunnies that hang around to meet travelers. It's such a sweet stop to make along the route and has so much to photograph, including massive vintage Route 66 signs and memorabilia.
Another great Missouri museum to visit is the Jesse James Museum in Sullivan. It's a very weird, but very cool interactive walking museum that takes you through the life of outlaw Jesse James and even questions his mysterious "death." The gift shop is loaded with kitschy Jesse James memorabilia, as well.
Your last Missouri stop should be at Gary's Gay Parita in Ash Grove: it's a verifiable Route 66 icon. As Gary says, “Folks from all over the world say it’s the dream of their life to travel Historic Route 66. It’s the dream of my life to meet those folks.” Owner Gary Turner loves the Mother Road and the people on it so much that he recreated a little retro Sinclair gas station, and spends his days welcoming travelers with a soda and great conversation.
Next up: Kansas! The Kansas section of Route 66 isn't what you'd call "lengthy", by any means. In fact, it's just 14 miles, but it's absolutely worth a visit. If you're coming in from Joplin, MO heading west, your first stop should be Galena, at the restored Kan-O-Tex service station now called "Cars on the Route". There are little snacks and sandwiches for sale, as well as antiques and Route 66 memorabilia. As part of their vision to connect visitors with the town, many of the items for sale are made by local craftspeople and artists. And what Route 66 service station would be complete without an old truck made to look like “Tow Mater,” from the Disney/Pixar film Cars?
One of the most popular roadside attractions along Route 66 is the Blue Whale of Catoosa, built by Hugh Davis in the early 1970s. He built the massive blue whale as a surprise anniversary gift for his wife Zelta, who loved whales and collected whale figurines. The whale has certainly seen better days, but it's a very cool stop. Take time to wander around the abandoned ruins of this famed roadside wonder, and have a picnic at one of the picnic tables. If you're lucky, the tamale wagon will be open and you can grab a tasty snack.
The historic Rock Cafe in Stroud is another iconic Route 66 stop. It also has a deep connection to the movie "Cars" and it was also featured on the show "Diners, Drive-Ins, and Dives." It's famous for its mouthwateringly golden-brown chicken-fried steak, and if you're in the mood for something sweet, try their Diet Doctor Pepper float.
Also, get a photo in front of Lucille's Famous Rt. 66 Gas Station in Hydro, OK. This historic two-story gas station was built by Carl Ditmore in 1929 in a very rural area... in fact the area is still very rural, but there's a nearby stream where locals go to find fossils and arrowheads.
Best time of year to travel along Route 66: The best time to road trip down Route 66 is between late April and early July, as well as late August through late October. The worst times to visit would be July and August, this is when the temperature is sweltering and all the kids are out of school, which means you'll come across some crowds along the route. In addition, July and August is considered high season, so you're going to be paying higher rates for lodging.