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HomeDestinationsRoute 667-Day Itinerary

AI-Generated Itinerary

7-Day Route 66 Itinerary

Your complete day-by-day guide to Route 66 — handpicked attractions, dining recommendations, and local tips for an unforgettable 7-day trip.

7 DaysRoute 66AI-CuratedFree & Personalised
7 days · 28 activities · Flexible plan
Personalise with AI
1

Day 1

Chicago Begin Sign to Springfield, Illinois (about 200 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 9:30 AM

Photo at the Route 66 Begin sign

Start at Adams Street and Michigan Avenue for the classic photo, then have breakfast at Lou Mitchell's on Jackson Boulevard.

Late Morning

9:30 AM - 1:00 PM

Joliet and the Gemini Giant

Drive southwest about 60 miles (1.5 hours with city traffic) via Joliet to Wilmington's towering Gemini Giant spaceman statue.

Afternoon

1:00 PM - 5:30 PM

Pontiac museum and Atlanta's giant

See the Route 66 Hall of Fame and Museum in Pontiac and the Paul Bunyon giant in Atlanta, then drive about 140 miles (2.5-3 hours) to Springfield.

Evening

5:30 PM - 9:00 PM

Corn dogs in Springfield

Eat at the Cozy Dog Drive In, a Route 66 landmark since 1949 that claims to have invented the corn dog on a stick.

2

Day 2

Springfield to Springfield, Missouri via St. Louis (about 300 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 10:00 AM

Chain of Rocks Bridge

Drive about 100 miles (1.5-2 hours) to the bridge and walk to its famous 22-degree bend over the Mississippi.

Late Morning

10:00 AM - 1:00 PM

Gateway Arch and frozen custard

Ride the tram up the 630-foot Gateway Arch (book timed tickets), then stop at Ted Drewes for a concrete of frozen custard.

Afternoon

1:00 PM - 5:30 PM

Ozarks drive via Cuba

Follow I-44 and old 66 about 215 miles (3.5-4 hours), stopping for the murals in Cuba and the giant rocking chair near Fanning.

Evening

5:30 PM - 9:00 PM

Cashew chicken in Springfield, Missouri

Try Springfield-style cashew chicken, the city's unique fried-chicken take on a Chinese-American classic.

3

Day 3

Kansas Corner to Oklahoma City (about 290 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 10:30 AM

Carthage, Galena and Kansas

Drive through Carthage, Missouri, then Galena, Kansas, where a rusty tow truck inspired a character in the movie Cars.

Late Morning

10:30 AM - 1:00 PM

Blue Whale of Catoosa

Photograph the smiling blue whale on its pond near Tulsa, one of the road's most beloved roadside attractions.

Afternoon

1:00 PM - 5:00 PM

Arcadia's Round Barn and POPS

Continue on the old road to Arcadia's 1898 Round Barn and POPS, with its 66-foot neon soda bottle and hundreds of sodas.

Evening

5:00 PM - 9:00 PM

Steak in Stockyards City

Have dinner at Cattlemen's Steakhouse, an Oklahoma City institution since 1910 in the historic Stockyards City district.

4

Day 4

Oklahoma City to Amarillo and Cadillac Ranch (about 260 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 10:30 AM

Oklahoma Route 66 Museum in Clinton

Drive about 85 miles (1.5 hours) west to Clinton for this excellent museum of the road's decades.

Late Morning

10:30 AM - 1:00 PM

U-Drop Inn in Shamrock, Texas

Cross into the Texas Panhandle to see this 1936 Art Deco gas station and cafe, an inspiration for the movie Cars.

Afternoon

1:00 PM - 5:00 PM

Panhandle drive to Amarillo

Drive about 100 miles past Groom's leaning water tower and giant cross to Amarillo, then check in.

Evening

5:00 PM - 9:00 PM

Cadillac Ranch at sunset

Bring spray paint to the ten buried Cadillacs west of town and add your mark as the sun goes down.

5

Day 5

Amarillo to Tucumcari Neon (about 115 miles)

4 activities · ~8 hrs

Morning

8:30 AM - 10:30 AM

Amarillo's Sixth Street

Stroll the historic Route 66 district on Sixth Street for antique shops, cafes and vintage storefronts.

Late Morning

10:30 AM - 1:00 PM

The Midpoint in Adrian, Texas

Stop at the sign marking halfway between Chicago and Los Angeles, and try a slice of pie at the long-running Midpoint Cafe.

Afternoon

1:00 PM - 5:00 PM

Tucumcari murals and motels

Cross into New Mexico (and Mountain Time, gaining an hour) and wander Tucumcari's colorful Route 66 murals.

Evening

5:00 PM - 9:00 PM

Neon night at the Blue Swallow

Check in to the 1939 Blue Swallow Motel and walk the strip as its famous neon sign glows after dark.

6

Day 6

Tucumcari to Gallup via Albuquerque (about 310 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 10:00 AM

Blue Hole of Santa Rosa

Drive about 60 miles to this clear, spring-fed pool, popular with divers and brave swimmers year-round.

Late Morning

10:00 AM - 1:00 PM

Green chile lunch in Albuquerque

Drive about 115 miles to Albuquerque for a green chile cheeseburger or enchiladas at a local diner.

Afternoon

1:00 PM - 5:30 PM

Old Town and Central Avenue neon

Walk Albuquerque's Old Town plaza and drive Central Avenue's restored neon signs, then continue about 140 miles to Gallup.

Evening

5:30 PM - 9:00 PM

El Rancho Hotel in Gallup

Spend the night at the 1937 El Rancho Hotel, where Hollywood stars stayed while filming Westerns.

7

Day 7

Petrified Forest, Winslow and on to Williams (about 215 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 11:00 AM

Petrified Forest National Park

Drive about 70 miles to the park and take the 28-mile road past the Painted Desert, Blue Mesa and Crystal Forest.

Late Morning

11:00 AM - 1:00 PM

Wigwam Motel in Holbrook

Photograph the concrete teepees and vintage cars at Holbrook's 1950 Wigwam Motel.

Afternoon

1:00 PM - 5:00 PM

Winslow and Flagstaff

Stand on the corner in Winslow, then climb into the pines at Flagstaff, about 7,000 feet up, before driving 30 miles to Williams.

Evening

5:00 PM - 9:00 PM

Route 66 main street in Williams

Have dinner and a stroll on Williams' neon-lit main street, the last Route 66 town bypassed by I-40, in 1984.

AI Personalisation

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Trip at a Glance

  • Route 66, United States
  • 7 days
  • Relaxed pacePlenty of time to explore at your own speed, with room for day trips.

Other Itineraries

  • 3-Day Route 66 ItineraryQuick highlights, perfectly paced
  • 5-Day Route 66 ItineraryMore time, more experiences
  • 10-Day Route 66 ItineraryThe ultimate getaway

Quick Tips

  • Book accommodation at least 2 weeks in advance
  • Get travel insurance before departure
  • Check visa requirements for your passport
  • Download offline maps before arrival
  • Notify your bank of your travel dates

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