About This Trip
The eastern half of the original Route 66 runs 1,300 miles from Chicago to Amarillo, Texas, cutting diagonally across the American heartland through Illinois, Missouri, Kansas, Oklahoma, and the Texas Panhandle. This is the half of the road where the diner-and-neon mythology lives — the stretch most readers picture when they hear 'Route 66.'
Begin at Lou Mitchell's in downtown Chicago, the unofficial start of the Mother Road, where milk-and-donut breakfasts have fortified Route 66 travelers since 1923. The road drops south through cornfields to Springfield, IL — home to the original cozy dog (the corn dog on a stick was invented here in 1946). Cross the Mississippi at the Chain of Rocks Bridge, the photogenic but disused old crossing into St. Louis.
Missouri rolls past Meramec Caverns (with its famous painted barn-roof billboards) and the Ozark foothills before the famously brief 13-mile Kansas section through Galena and Baxter Springs. Oklahoma is the longest Route 66 state at 432 miles — Tulsa's deco architecture, the Blue Whale of Catoosa, and the Round Barn at Arcadia are can't-miss stops. The Texas Panhandle is short but iconic: Shamrock's restored U-Drop Inn (the inspiration for Ramone's body shop in Cars) and Amarillo's Cadillac Ranch — ten half-buried Cadillacs covered in decades of spray paint — are the eastern half's exclamation point.
Best for: road-trip romantics, photographers, Americana fans, anyone who wants to drive the most-Googled road trip in the world without committing to all 2,400 miles.
Best time to drive: April through June and September through October. Summers in the southern stretch can be brutal; winters can bring ice from Illinois through Oklahoma. Allow 5 to 7 days unhurried.
Stops
Chicago, IL — Lou Mitchell's & the Start
The Mother Road begins downtown on East Adams Street at Michigan Avenue. Lou Mitchell's, a few blocks west, has fueled Route 66 travelers with milk-and-donut breakfasts since 1923. Grab the iconic 'Route 66 Begin' sign photo before rolling south out of the city.
Springfield, IL — Cozy Dog Drive In
Home of Abraham Lincoln's tomb and the original cozy dog — the cornmeal-battered hot dog on a stick was invented here in 1946 by Ed Waldmire. The drive-in is still run by his descendants. Walk a block of the old route through downtown after.
St. Louis, MO — Gateway Arch & Chain of Rocks Bridge
Cross the Mississippi on the historic Chain of Rocks Bridge (now pedestrian-only) for the most photogenic Route 66 river crossing. The Gateway Arch is a worthwhile detour — the tram ride to the top is genuinely impressive.
Tulsa, OK — Deco Heart of the Mother Road
Tulsa has the country's finest concentration of Art Deco architecture, much of it lining the original Route 66 alignment. Don't miss the Meadow Gold neon sign, the Cyrus Avery Centennial Plaza, and the Blue Whale of Catoosa just east of town.
Oklahoma City, OK — Round Barn & Pops 66
The 1898 Round Barn in Arcadia (just east) is one of the most photographed structures on Route 66. Pops 66 down the road is a modern roadhouse with 600+ varieties of soda and a giant neon bottle out front.
Shamrock, TX — U-Drop Inn
The restored 1936 Conoco station and U-Drop Inn café is the most beautiful piece of Art Deco roadside architecture on Route 66, and the visual inspiration for Ramone's body shop in Pixar's Cars. Currently houses the town's visitor center.
Amarillo, TX — Cadillac Ranch
Ten Cadillacs buried nose-down in a field west of Amarillo, planted in 1974 by the Ant Farm art collective. Bring spray paint — the cars are repainted daily by visitors and the whole installation is an evolving collaborative artwork. The natural break point before continuing Route 66 West.