The Ultimate Route 66 Road Trip To California

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

  • 35
  • 36:09
  • 2,198 mi
  • $420
Take This Trip

Created by klytwynec - July 11th 2020

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 The Art Institute of Chicago
5.0

111 S Michigan Ave, Chicago, IL, US

The Art Institute of Chicago

Date: August 3, 2020

1
22mi 00h 29m

645 Joliet Rd, Willowbrook, IL, US

Dell Rhea's Chicken Basket

1

Date: August 3, 2020

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.

2
126mi 02h 05m
Photo of Funks Grove Pure Maple Sirup
3.4

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

Funks Grove Pure Maple Sirup

2

Date: August 3, 2020

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.

3
158mi 02h 32m

6726 Chippewa St, St. Louis, MO, US

Ted Drewes Frozen Custard

3

Date: August 3, 2020

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.

4
101mi 01h 38m
Photo of Super 8 Rolla
3.0

1641 Martin Springs Drive, Rolla, MO, US

Super 8 Rolla

FastBook
$

Click to discover a
great deal!

4

Date: August 3, 2020

5
22mi 00h 23m
Photo of Uranus Missouri
4.4

14400 Highway Z, St. Robert, MO, US

Uranus Missouri

5
6
91mi 01h 29m
Photo of Fantastic Caverns
4.5

4872 N Farm Road 125, Springfield, MO, US

Fantastic Caverns

6

Date: August 4, 2020

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.

7
85mi 01h 32m

119 N Main St, Galena, KS, US

Cars on the Route

7

Date: August 4, 2020

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?

8
48mi 00h 51m

319 E Illinois Ave, Vinita, OK, US

Clanton's Cafe

8

Date: August 4, 2020

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.

9
47mi 00h 45m
Photo of Blue Whale of Catoosa
4.1

2680 N Highway 66, Catoosa, OK, US

Blue Whale of Catoosa

9

Date: August 4, 2020

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.

10
65mi 01h 03m

114 W Main St, Stroud, OK, US

Rock Cafe

10

Date: August 4, 2020

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.

11
13mi 00h 17m
Photo of Lincoln Motel
3.0

740 E 1st St, Chandler, OK, US

Lincoln Motel

FastBook
$

Click to discover a
great deal!

11

Date: August 4, 2020

Oklahoma also has its share of retro Route 66 hotels (notable today for their vintage signage). A few of the more famous ones along the route are the Desert Hills Motel in Tulsa, the Skyliner Motel in Stroud, and the Lincoln Motel in Chandler.

12
27mi 00h 31m
Photo of Arcadia Round Barn
4.5

107 E. Highway 66, Arcadia, OK, US

Arcadia Round Barn

12
13
0mi 00h 01m

660 W Hwy 66, Arcadia, OK, US

POPS Soda Ranch

13

Date: August 5, 2020

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.

14
84mi 01h 20m
Photo of Lucille's Famous Rt. 66 Gas Station
3.6

Old Route 66, Hydro, OK, US

Lucille's Famous Rt. 66 Gas Station

14

Date: August 5, 2020

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.

15
23mi 00h 24m
Photo of Oklahoma Route 66 Museum
4.5

2229 W Gary Blvd, Clinton, OK, US

Oklahoma Route 66 Museum

15

Date: August 5, 2020

16
79mi 01h 14m

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

Tower Station and U-Drop Inn Café

16

Date: August 5, 2020

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 22m
Photo of Phillips 66 on the Route
3.5

219 Gray St, McLean, TX, US

Phillips 66 on the Route

17

Date: August 5, 2020

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
46mi 00h 44m
Photo of VW Slug Bug Ranch
4.1

Interstate 40 Frontage Road, Panhandle, TX, US

VW Slug Bug Ranch

18

Date: August 5, 2020

19
22mi 00h 22m

7701 E I-40, Amarillo, TX, US

The Big Texan Steak Ranch

19

Date: August 5, 2020

No Route 66 trip through Texas would be complete without a big Texan-style meal. Do yourself a favor and head to The Big Texan Steak Ranch. It's a Route 66 legend with its 72oz steak challenge, which began way back in 1962. Just a couple years after owner Bob Lee opened the doors he noticed the influx of hungry cowboys on their paydays looking to down some hearty steaks. One Friday in 1962 he set up an eating contest to see who could eat the most one-pound steaks in an hour. After one cowboy downed 72oz worth of steak (along with a salad, a shrimp cocktail, and a baked potato) Lee declared that anyone who could eat that much steak in an hour gets it for free... and so a legend was born.

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.