The romance of the Great American Road Trip began with the “Mother Road”, Route 66. From big cities to swaths of endless desert, Route 66 is Americana at its finest where the drive is just as exciting as the destination. The storied journey begins in the heart of Chicago and ends 2,448 miles west on the Santa Monica Pier in California. While there are many places to stop along the way, we have separated the trip into six manageable legs that highlight dozens of kitschy pit stops.
Chicago, IL to St. Louis, MO
Photo op: Take a photo at the “Begin Historic Route 66” sign which is located on the corner of E Adams Street and Michigan Avenue. Drop into the Art Institute of Chicago before you hit the road which is located directly behind the street sign.
Pit Stop: Visit St. Louis Arch
While you might be familiar with the famed St.Louis Arch, the monument is far more awe inspiring in person. Take the tram tour to the top of the 630 ft building for sweeping views of the Mound City.
Where to Stay: The Last Hotel STL
The Last Hotel transports guests back to an era of industry in St.Louis. Graced with original Art Deco details and ornate carvings, this former shoe factory is the perfect place to live in history for a night.
St.Louis, MO to Oklahoma City, OK
Pit Stop: Route 66 Interpretive Center
Any journey down the Mother Road is not complete without a trip to the Route 66 Interpretive Center. The museum takes guests through the birth of the road trip and how Route 66 embodies the American dream.
Where to Stay: 21c Museum Hotel Oklahoma City
Part contemporary art museum, part hotel, 21c Museum Hotel is the stimulating stop over befitting of your trek. Housed in a former Ford Motor Company assembly plant, the hotel embraces its heritage highlighting open, clean spaces while bringing to life the original fixtures of the building.
Oklahoma City, OK to Amarillo, TX
Pit Stop: Cadillac Ranch
Driving down Route 66 you might mistake this sculpture for an accident until you get a little closer. Upended graffitied cars stand defiantly along the side of the road. It’s campy and odd, everything you are craving on your road trip.
Where to Stay: The Barfield, Autograph Collection
The Barfield, Autograph Collection is the luxe respite that redefines typical road trip accommodations. The hotel embraces the cattle culture of the panhandle with chic touches like a “hidden” speakeasy all in the heart of Amarillo.
Amarillo, TX to Albuquerque, NM
Pit Stop: Laguna Pueblo
A historic domain that’s a capsule of Native American culture — in fact, it’s the largest Keresan-speaking pueblo existing today.
Where to Stay: El Vado Motel
Staying in a motel is a right of passage while traversing the Mother Road. El Vado Motel gives guests all the kitsch of a classic roadside motel with the elegant touches of a high end boutique accommodation.
Albuquerque, NM to Flagstaff, AZ
Pit Stop 1: Oatman, AZ Ghost Town
Ghost Towns are small areas of buildings, once bustling with people, now deserted, mostly due to economic failure. The former mining town of Oatman has become a staple roadside attraction with reenactors taking visitors back to the town’s glory days in the early 1900’s.
Pit Stop 2: The Grand Canyon
While this bucket list National Park is not on Route 66, it’s worth deviating from the path to see this geological marvel.
Where to Stay: Under Canvas Grand Canyon
Under Canvas is a glamping collective with all the comforts of a hotel founded in outdoor living. Expect spectacular safari style tent accommodations, delicious cuisine, and cozy wood burning stoves.
Flagstaff, AZ to Los Angeles, CA
Photo Op: Bookend your trip with a photo at the Route 66 “End of the Trail” sign. Once you hit Santa Monica, get out of your car and stroll down the pier where you will find the road sign that ends your trip.
Pit Stop: Roy’s Motel
After traveling for miles along a desert road, you may think the retro motel in the distance is a mirage. Roy’s Motel is no longer active, but you can still stop by the vintage attraction to fill up your tank and grab a quick photo before continuing on your way.
Where to Stay: Hotel Casa del Mar
After completing your journey, you deserve to bask in luxury for a few days. Hotel Casa del Mar sits perched at the end of your journey seaside in Santa Monica offering Mediterranean-inspired accommodations and a rejuvenating spa.
Other articles you may like: