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Route 66
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The ultimate Route 66 road trip

Take your time exploring 'The Mother Road' with this ultimate Route 66 road trip itinerary.

Written by Lauren Mack for Time Out, in partnership with Mobil 1

The most iconic American road trip is the 2,451-mile Route 66, one of America's original highways. Recently, this road well-traveled has faced a retro renaissance with renewed popularity from travelers eager for slow travel and a classic road trip.

Established in 1926 and completed in the 1930s, Route 66 was the primary highway for folks seeking to drive to the west coast. Connecting Chicago to Santa Monica, California, Route 66 passes through eight states (Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California). 

What makes the multi-day road trip appealing are the slices of 20th century Americana and kitsch: mom-and-pop motels, retro soda fountains and service stations, neon-lit diners, and quirky roadside attractions. Follow our ultimate road trip itinerary so you won't miss any of the nostalgic fun.

Route 66 road trip

Begin Route 66 Sign | Chicago, IL
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1. Begin Route 66 Sign | Chicago, IL

The start of The Mother Road is marked by a sign on the northwest corner of Adams Street and Michigan Avenue. One block over on the south side of East Jackson Boulevard is the End Route 66 Sign for drivers who began their journey in California and drove east.

Route 66 Hall of Fame & Museum | Pontiac, IL
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2. Route 66 Hall of Fame & Museum | Pontiac, IL

The Route 66 Association of Illinois Hall of Fame and Museum is packed with thousands of Route 66 artifacts and memorabilia. Don't miss a photo in front of the Route 66 shield mural on the back of the museum's exterior wall—it's the largest Route 66 shield mural in the world.

Cozy Dog Drive In | Springfield, IL
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3. Cozy Dog Drive In | Springfield, IL

What started as a desire in the 1940s to find a quicker way to make a corn dog, a hotdog encased in batter, turned into "Cozy Dogs," hot dogs on a stick that could be French-fried. You can try Ed Waldmire Jr.'s quirky creation at the Cozy Dog Drive In, which opened in 1949 and is now run by Waldmire's grandson.

4. Doc's Just Off 66 | Girard, IL

Take a sip of nostalgia and a walk back in time at Doc's Just Off 66. After 117 years as a pharmacy that was established in 1884, it changed owners and was renamed Doc's Soda Fountain. In 2021, Steve and Casey Claypool purchased the spot and fully renovated the soda fountain while keeping some relics from its past life such as old patient medicines and remedies, early equipment, and advertisements on display.

Soulsby Service Station | Mount Olive, IL
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5. Soulsby Service Station | Mount Olive, IL

Gas hasn't been pumped at this old school gas station since 1991, but the charming spot is still worth a stop. Soulsby Service Station was built in 1926 by Henry Soulsby. When the station stopped selling gas in the '90s, its proprietors continued to check oil and sell soda pop until the station was shuttered in 1993. The restored station is now owned by Mike Dragovich and is on the National Register of Historic Places.

Dell Rhea's Chicken Basket | Willowbrook, IL
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6. Dell Rhea's Chicken Basket | Willowbrook, IL

What began as a gas station lunch counter, Dell Rhea's Chicken Basket is still going strong 75 years later with its world famous fried chicken. Featured on the TV show Diners, Drive-Ins & Dives, Dell Rhea's Chicken Basket is also on the National Register of Historic Places.


7. Funks Grove Pure Maple Sirup | Shirley, IL

Since 1824, the Funk family has been making sirup (the product made by boiling sap). Today, the family draws sap from 6,000 taps, producing 2,000 gallons of maple sirup each season (typically March through August). The sirup, and the family's famous pure maple candy, is sold at its roadside Funks Grove Pure Maple Sirup

Route 66 Rocker | Cuba, MO
Photograph: Scott Snowden

8. Route 66 Rocker | Cuba, MO

Formerly the world's largest rocking chair, Route 66 Rocker was imagined by Dan Sanazaro, who wanted to attract drivers to his shop. The massive 42ft, one-inch steel rocker rocked when it was first installed, but the rocking chair has since been welded to its base. Years on, it remains a popular spot for a photo op.

Ted Drewes Frozen Custard | St. Louis, MO
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9. Ted Drewes Frozen Custard | St. Louis, MO

No drive through the Missouri stretch of Route 66 is complete without a stop at Ted Drewes Frozen Custard for custard. Drewes first set up shop in Florida in 1929 and opened a location on Route 66 in 1941. The most popular frozen treat is the Concrete, a thick malted shake that is served upside down. The family is also famous for seasonally selling Canadian Balsam Fir Christmas trees, transported directly from their family farm in Nova Scotia.

Route 66 Museum | Clinton, OK
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10. Route 66 Museum | Clinton, OK

With exhibits arranged by decade, the Route 66 Museum is brimming with Route 66 memorabilia, including a neon Route 66 sign, a classic car, and vintage highway signs. The museum includes exhibits on the highway's construction, the Dust Bowl, and the Big Band era.

POPS | Arcadia, OK
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11. POPS | Arcadia, OK

This newer, modern roadside addition embraces the retro vibes of Route 66 with a 66-foot-tall LED soda pop bottle, a collection of 12,000 soda pop bottles, and 650 kinds of soda for sale. POPS has a gas station, convenience store, restaurant, and lots and lots of soda pop.

Waylan’s Hamburgers the Ku-Ku | Miami, OK
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12. Waylan’s Hamburgers the Ku-Ku | Miami, OK

With so many places along Route 66 serving hamburgers, Waylan's Hamburgers the Ku-Ku stands out thanks to its restaurant building that resembles a giant cuckoo clock. The retro burger joint has a drive thru to eat on-the-go and a throwback dining room. Fill up on old school comfort foods like hamburgers, fries, and shakes.

Tower Station and U-Drop Inn Cafe | Shamrock, TX
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13. Tower Station and U-Drop Inn Cafe | Shamrock, TX

What was once a Conoco gas station and a popular Route 66 cafe is now home to Shamrock, Texas's Chamber of Commerce. This historic spot is worth a stop and a photo op for its Art Deco detailing – evocative of the heyday of Route 66. The Tower Station's spire still boasts the C-O-N-O-C-O letters, beckoning travelers to stop and fill'er up.

Route 66 Midpoint | Adrian, TX
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14. Route 66 Midpoint | Adrian, TX

The midpoint of Route 66 is worth pulling over for. Look for the white line on the road and a sign noting the 1,139-mile distance from the midpoint to either Chicago or Los Angeles. 

Cadillac Ranch | Amarillo, TX
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15. Cadillac Ranch | Amarillo, TX

Created in 1974 by Stanley Marsh 3 and The Ant Farm, a group of hippie-artists, the Cadillac Ranch is a roadside art installation featuring 10 Cadillacs positioned vertically into the dirt of a Texas field. The angled cars range from a 1949 Cadillac Club Sedan to a 1963 Cadillac Sedan deVille. Over the years, visitors have stripped off pieces of the cars to take as souvenirs. Today, visitors are welcome to come and graffiti the colorful cars.

Blue Hole | Santa Rosa, NM
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16. Blue Hole | Santa Rosa, NM

Stop for a refreshing swim or SCUBA dive at the Blue Hole, a bell-shaped artesian lake adjacent to Route 66. The crystal clear sapphire waters are as alluring to motorists as they are refreshing. The water is a constant 62 degrees Fahrenheit –  truly an oasis in the middle of the desert.

Oatman Hotel | Oatman, AZ
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17. Oatman Hotel | Oatman, AZ

The former gold mining boomtown of Oatman, Arizona was used as the set for the 1962 film How the West Was Won. Built in 1902, the Oatman Hotel is a two-story adobe structure where Clark Gable and Carole Lombard stayed after their wedding in 1939. The hotel is rumored to be haunted by Oatie the Ghost.

Grand Canyon Caverns | Peach Springs, AZ
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18. Grand Canyon Caverns | Peach Springs, AZ

Created over 65 million years ago, the Grand Canyon Caverns are the largest dry caverns in the United States. Located 210 feet underground, the caverns boast a restaurant (one of the few underground restaurants in the world) and a suite for folks who want to spend a night underground.

Route 66 Memorabilia & Visitor’s Center | Seligman, AZ
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19. Route 66 Memorabilia & Visitor’s Center | Seligman, AZ

The Route 66 Memorabilia & Visitor’s Center is the original Route 66 gift shop, selling a range of souvenirs for travelers of The Mother Road. Owned by Angel and Vilma Delgadillo, the family-run shop sells stickers, magnets, patches, pins, clothing, and more.

Delgadillo's Snow Cap | Seligman, AZ
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20. Delgadillo's Snow Cap | Seligman, AZ

Juan and Mary Delgadillo established Delgadillo's Snow Cap, a drive-in burger joint, in 1953. Juan built the restaurant from scrap lumber he collected while working for the railroad. Juan later became a co-founder of Historic Route 66, a locals'-led initiative to preserve original sections of Route 66.


21. Red Garter Inn | Williams, AZ

Built in 1897, this former bordello and saloon housed in a two-story Victorian Romanesque brick building has been painstakingly restored by John Holst. The four-room Red Garter Inn has a cafe, the Grand Canyon Coffee and Café, and endless charm. The Madam's Room has its original skylight while Big Bertha's Room boasts an original claw-footed bathtub and views of historic downtown Williams from the balcony.

Elmer's Bottle Tree Ranch | Oro Grande, CA
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22. Elmer's Bottle Tree Ranch | Oro Grande, CA

The creator of this glass bottle wonderland passed away in 2019, but Elmer Long's Bottle Tree Ranch continues to grow in popularity. Long began collecting glass soda bottles and, as an adult, hung these glass soda bottles and wine bottles onto metal pipes, forming a garden of glass. The result is a kaleidoscope of color when the sun shines upon the bottle ranch.

Route 66 Sign | Santa Monica, CA
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23. Route 66 Sign | Santa Monica, CA

Since 2009, drivers who complete the drive on Route 66 can commemorate it with a selfie in front of an official sign marking the end of the Mother Road. The large sign, which is at Santa Monica Pier, says “Santa Monica 66 End of the Trail.” It, and the memories of driving Route 66, is the ultimate souvenir. 

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