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The Ultimate Route 66 Road Trip

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

  • 41
  • 39:60
  • 2,352 mi
  • $325
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Created by original21 - July 28th 2019

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
4.0

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.

1
40mi 00h 45m
The Gemini Giant
4.0

810 E. Baltimore Street, Wilmington, IL, US

The Gemini Giant

1
Pasfield House Inn
4.4

525 South Pasfield Street, Springfield, IL, US

Pasfield House Inn

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.

2
146mi 02h 21m

401 S 2nd St, Springfield, IL, US

Illinois State Capitol

2
3
1mi 00h 09m
Abraham Lincoln Home
4.4

413 S 8th St, Springfield, IL, US

Abraham Lincoln Home

3
4
45mi 00h 50m
Litchfield History Museum & Route 66 Welcome Center
4.3

Old Route 66 N, Litchfield, IL, US

Litchfield History Museum & Route 66 Welcome Center

4
5
0mi 00h 01m
Jubelt's Bakery & Restaurant
4.0

303 N Old Route 66, Litchfield, IL, US

Jubelt's Bakery & Restaurant

5
6
0mi 00h 01m
Ariston Cafe
4.5

413 N Old Route 66, Litchfield, IL, US

Ariston Cafe

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7
17mi 00h 20m
Pink Elephant Antiques
4.4

908 Veterans Memorial Dr., Livingston, IL, US

Pink Elephant Antiques

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8
39mi 00h 43m
Gateway Arch National Park
4.5

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

Gateway Arch National Park

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9
9mi 00h 17m
Ted Drewes Frozen Custard
4.6

6726 Chippewa, St. Louis, MO, US

Ted Drewes Frozen Custard

9

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.

10
76mi 01h 17m
Murals of Cuba, MO
3.5

112 N Filmore St, Cuba, MO, US

Murals of Cuba, MO

10

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.

11
132mi 02h 04m
Best Western Route 66 Rail Haven
4.6

203 S Glenstone Avenue, Springfield, MO, US

Best Western Route 66 Rail Haven

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11
12
27mi 00h 31m
Gary's Gay Parita
4.7

21118 Old 66, Ash Grove, MO, US

Gary's Gay Parita

12

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.

13
149mi 02h 15m
Blue Whale of Catoosa
4.1

2680 N Highway 66, Catoosa, OK, US

Blue Whale of Catoosa

13

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.

14
65mi 01h 02m
Rock Cafe
4.0

114 W Main St, Stroud, OK, US

Rock Cafe

14

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.

15
40mi 00h 41m
POPS Soda Ranch
3.9

660 W Highway 66, Arcadia, OK, US

POPS Soda Ranch

15

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.

16
186mi 02h 53m

101 E. 12th Street, Shamrock, TX, US

Tower Station and U-Drop Inn Café

16

On to Texas! The Lone Star state still has about 150 miles of Route 66 road still remaining, and it all closely parallels Interstate 40, so it's easy to hop on and off the patches of Mother Road. A few highlights include Shamrock, Texas, which is home to the Conoco Tower. This once-bustling stop along the route remains a great place to take pictures to this day. Of all the gas stations, open or closed, in America, this may be one of the most stunning. It’s just a hop, skip, and jump off I-40, so you really have no excuse not to stop and see this roadside classic. While you’re in Shamrock, also hit up their very own Blarney Stone.

17
20mi 00h 20m
Phillips 66 on the Route
3.4

219 Gray St, McLean, TX, US

Phillips 66 on the Route

17

Another great little Texas town to visit is McLean. Here you can stop at the Phillips 66 on the Route, a vintage 1928 gas service station that was designed in what was known as "Cottage Fashion," because it resembled a little country cottage. Adorable!

18
0mi 00h 01m
Cactus Inn
4.1

101 Pine Street, McLean, TX, US

Cactus Inn

18

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.