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SC & JF - Route 66 Road Trip

The ultimate guide to seeing the best of Route 66 in one week.

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Created by scampos - October 29th 2017

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.

Photo of Route 66 Starts Here Sign
3.4

65 E Adams St, Chicago, IL, US

Route 66 Starts Here Sign

Photo of Ambler's Texaco Gas Station
4.5

W Waupansie St, Dwight, IL, US

Ambler's Texaco Gas Station

105 S Old Rte 66, Dwight, IL, US

Old Route 66 Family Restaurant

Photo of Illinois Route 66 Hall of Fame and Museum
4.5

110 W Howard St, Pontiac, IL, US

Illinois Route 66 Hall of Fame and Museum

1887 Pj Keller Hwy, Lexington, IL, US

Barker Chevrolet

6th street, Springfield, IL, US

Cozy Dog Drive-In

1107 Historic Old Rte 66, Staunton, IL, US

Henry's Rabbit Ranch

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.

913 E Washington St, Cuba, MO, US

Missouri Hick Barbeque

Photo of Wagon Wheel Motel
3.5

901 E Washington St, Cuba, MO, US

Wagon Wheel Motel

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Photo of Murals of Cuba, MO
3.8

112 N Filmore St, Cuba, MO, US

Murals of Cuba, MO

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.

Photo of Munger Moss Motel
4.4

1336 E Route 66, Lebanon, MO, US

Munger Moss Motel

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1950 E Primrose St, Springfield, MO, US

Cheddar's INC

Photo of Gary's Gay Parita
4.7

21118 Old 66, Ash Grove, MO, US

Gary's Gay Parita

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.

Photo of Boots Court
4.5

107 S Garrison Ave, Carthage, MO, US

Boots Court

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910 S Garrison Ave, Carthage, MO, US

Cave Gang Pizza & Pub

301 S Garrison Ave, Carthage, MO, US

Pancake Hut

119 N Main St, Galena, KS, US

Cars on the Route

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?

114 W Main St, Stroud, OK, US

Rock Cafe

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.

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.