The Ultimate Route 66 Road Trip

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

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Created by RobBob - October 11th 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.

Dell Rhea's Chicken Basket
4.1

645 Joliet Rd (Historic Rt 66), 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.

The Gemini Giant
4.0

810 E. Baltimore Street, Wilmington, IL, US

The Gemini Giant

Ambler's Texaco Gas Station
4.5

W Waupansie St, Dwight, IL, US

Ambler's Texaco Gas Station

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

Funks Grove Pure Maple Sirup
3.4

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.

Bunyon With a Hotdog
4.4

110 Southwest Arch Street, Atlanta, IL, US

Bunyon With a Hotdog

Route 66 Arcade Museum
4.4

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.

Railsplitter Covered Wagon
4.0

1750 5th street, Lincoln, IL, US

Railsplitter Covered Wagon

Cozy Dog Drive In
4.0

6th street, Springfield, IL, US

Cozy Dog Drive In

Whirl A Whip
3.6

3rd St, Girard, IL, US

Whirl A Whip

Pink Elephant Antiques
4.4

908 Veterans Memorial Dr., Livingston, IL, US

Pink Elephant Antiques

Luna Cafe
3.4

201 E Chain Of Rocks Rd, Granite City, IL, US

Luna Cafe

Ted Drewes Frozen Custard
4.6

6726 Chippewa, 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.

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.

Murals of Cuba, MO
3.7

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.

Fantastic Caverns
4.5

4872 N Farm Road 125, Springfield, MO, US

Fantastic Caverns

If you want a break from driving, pull over at the Fantastic Caverns in Springfield, and explore the world that exists underneath Route 66. It's North America's only completely ride-through cave tour, and it's absolutely worth the 55 minute tram ride.

Devils Elbow, Missouri, United States

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.

Cars on the Route
4.4

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?

1015 North Main, Miami, OK, US

The Frozen Elephant

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.