The Ultimate Route 66 Road Trip

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

  • 43
  • 39:16
  • 2,354 mi
  • $463
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Created by lindavermeulen - May 10th 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.

Chicago O'Hare International Airport, Des Plaines, Illinois United States

21mi 00h 27m

645 Joliet Rd, Willowbrook, IL, US

Dell Rhea's Chicken Basket


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.

127mi 01h 60m
Photo of Funks Grove Pure Maple Sirup

5257 Historic U.S. 66, Shirley, IL, US

Funks Grove Pure Maple Sirup


For those of you with a sweet tooth, Funks Grove Pure Maple Sirup in Shirley, IL produces over 1,800 gallons of maple syrup using old-fashioned techniques, and it's all bottled in beautiful, vintage-looking bottles.

10mi 00h 16m
Photo of Route 66 Arcade Museum

Atlanta, IL, US

Route 66 Arcade Museum


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.

46mi 00h 48m
Photo of Pasfield House Inn

525 South Pasfield Street, Springfield, IL, US

Pasfield House Inn


Date: June 29, 2017

58mi 00h 58m

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.

39mi 00h 41m
Photo of Gateway Arch

11 North 4th Street, St. Louis, MO, US

Gateway Arch

9mi 00h 13m

6726 Chippewa St, St. Louis, MO, US

Ted Drewes Frozen Custard


As you drive through Missouri, there's a couple must-eat places once you hit St. Louis, including the classic 60-year old Eat-Rite Diner, which is like stepping back in time. Afterwards, polish off your meal with dessert at another Route 66 icon, Ted Drewes Frozen Custard.

6mi 00h 13m
Photo of Laumeier Sculpture Park & Museum

12580 Rott Rd, St. Louis, MO, US

Laumeier Sculpture Park & Museum


While in St. Louis, stretch your legs with a visit to the Laumeier Sculpture Park & Museum. Here you can get a great picture of a gigantic, massive, eyeball in the middle of a field. It's pretty wild and fun to walk around the outdoor art exhibits.

47mi 00h 45m

I-44 - Exit 230, Sullivan, MO, US

Jesse James Museum


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.

Photo of Wagon Wheel Motel

901 E Washington St, Cuba, MO, US

Wagon Wheel Motel


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Date: June 29, 2017

30mi 00h 28m
Photo of Murals of Cuba, MO

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.

204mi 04h 02m
Photo of Gary's Gay Parita

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.

68mi 01h 08m

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?

47mi 00h 48m

319 E Illinois Ave, Vinita, OK, US

Clanton's Cafe


When you're hungry, head to Clanton's Cafe in Vinita, OK. This retro Route 66 restaurant is best-known for its breakfast, local cuisine, which includes their world-famous chicken fried steak and calf fries.

47mi 00h 47m
Photo of Blue Whale of Catoosa

2680 N Highway 66, Catoosa, OK, US

Blue Whale of Catoosa


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.

19mi 00h 22m

9518 S 86th East Ave, Tulsa, Oklahoma United States


Date: June 30, 2017

52mi 00h 49m

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.

40mi 00h 40m

660 W Hwy 66, Arcadia, OK, US

POPS Soda Ranch


After all that driving, you're probably thirsty. Head over to POPS Soda Ranch in Arcadia. This is a landmark gas station and diner, but the real draw here is the hundreds of sodas they offer. Plus, there's a massive 66-ft tall soda bottle out front for a great photo-op.

85mi 01h 20m
Photo of Lucille's Famous Rt. 66 Gas Station

Old Route 66, Hydro, OK, US

Lucille's Famous Rt. 66 Gas Station


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.