Route 66
Chicago, IL → Santa Monica, CA · ~2,448 miles · 2 weeks
Stylized illustration, not a photo — the real place looks different (and that’s half the fun).
America’s most famous road trip strings eight states together with neon motels, giant roadside oddities, and diners that have been frying since the Mother Road’s heyday.
Good to know: Book the small-town landmark motels (Tucumcari, Williams, Seligman) weeks ahead — they sell out, especially in the 2026 Centennial year.
Updated July 2026.
The Mother Road, Chicago to the Pacific.
It’s the original American road trip — and still the best collection of roadside Americana on one stretch of asphalt. Half the fun is the kitsch between the cities.
States on this route
The signature stops
What to pull over for.
The best stops on the Route 66 are the places that define the drive, not just the nearest towns. Roamward orders them for the road: start with Cozy Dog Drive In, Meramec Caverns, Blue Whale of Catoosa, Cadillac Ranch, then open each stop guide for the pull-over context.
01Cozy Dog Drive InSpringfield diner where the corn dog was perfected — open the stop guideIL
02Meramec Cavernsbillboard-famous Ozark show cave and old outlaw hideout — open the stop guideMO
03Blue Whale of Catoosaa beloved 80-foot concrete whale in a roadside swimming hole — open the stop guideOK
04Cadillac Ranchten graffiti-covered Cadillacs planted nose-down near Amarillo — open the stop guideTX
05Blue Hole of Santa Rosaan 80-foot artesian spring of impossibly clear blue water — open the stop guideNM
06Standin’ on the Cornerthe Winslow corner the Eagles made famous — open the stop guideAZ
07Santa Monica Pierthe official end-of-the-trail sign over the Pacific — open the stop guideCA
Going the distance? Read the full Route 66 Centennial guide — the full stop-by-stop itinerary.
Where to eat
Restaurants along this route.
Restaurants on the Route 66 are chosen for trip usefulness: gateway-town location, a clear reason to stop, and enough quality to make a traveler save the pick. Start with Lou Mitchell's, The Berghoff, Cozy Dog Drive In, Fred & Red's.
A curated set of trip-useful meals near the route — enough to anchor driving days without turning the guide into a phone book.
- Lou Mitchell's
The classic Chicago Route 66 breakfast sendoff — old-school diner energy before the first highway miles.
- The Berghoff
A century-plus Chicago Loop standby for a proper sit-down meal at the eastern end of the Route 66 story.
- Cozy Dog Drive In
A Route 66 original in Springfield, Illinois, built around the battered hot dog on a stick that became a road-food icon.
- Fred & Red's
A revived Joplin chili counter with deep local history, perfect when the Missouri segment needs something compact, cheap, and rooted.
- Casper's Diner
A compact Springfield diner for chili, burgers, and old-road charm in the Missouri stretch of Route 66.
- Crown Candy Kitchen
Historic soda-fountain sweetness in St. Louis — a great counterpoint to neon, motels, and heavy road food.
- Donut Drive-In
Neon-signed 1953 donut stand on Chippewa Street still working its original recipes — voted the best donuts on all of Route 66. Doors open at 5am for the road-trip breakfast of champions.
- Ted Drewes Frozen Custard
The St. Louis Route 66 dessert stop: fast-moving lines, frozen custard, and a mandatory concrete if the weather cooperates.
- Jiggs Smokehouse
A family-run Route 66 smokehouse near the I-40 frontage plating smoky brisket and towering specialty sandwiches like the pork-rib Pig Sickle.
- White Dog Hill
A first-class steak-focused restaurant set in the native red-stone former country club clubhouse, prized for succulent steaks and sweeping Route 66 sunset views.
- 66 Sweet Spot
A small Elk City treat stop for the western Oklahoma run, best used as a quick morale lift between museum stops and longer prairie miles.
- Country Dove
A gift-and-tea-room lunch spot off Route 66 in Elk City, beloved for homemade soups, sandwiches and its signature French silk pie.
Build a trip around Route 66 drive.
Save catalog-backed stops to My Trips on the web now. The iOS beta is testing the on-road companion: verified check-ins, badges, shared trips, and your growing map of America.
Stay & experience
Find a place to stay near Route 66, Illinois.
Hotels, cabins, and rentals close to the action — compare and book for your trip.
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Things to do near Route 66
Browse guided tours and bookable activities that fit this stop.
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