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.
Milwaukee Veteran Affairs
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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.
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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.
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Another Missouri town that will make you feel like you're traveling back in time is Cuba, and while there, you should tour the Murals of Cuba, which take you on an artistic journey through the rich history of the area.
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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.
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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.