5-Day Route 66 Itinerary

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.

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.

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.

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.

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.

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.

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.

Cashew chicken in Springfield, Missouri

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

Carthage, Galena and Kansas

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

Blue Whale of Catoosa

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

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.

Steak in Stockyards City

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

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.

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.

Panhandle drive to Amarillo

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

Cadillac Ranch at sunset

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

Amarillo's Sixth Street

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

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.

Tucumcari murals and motels

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

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.