The Essential Route 66 Roadtrip Guide

It’s easy to get so focused on international travel that we end up missing all our own country has to offer. So today we’re talking about our favorite way to experience the U.S: a classic road trip. From Chicago to Santa Monica, you’ll be stopping at drive in donut shops, old general stores, the world’s largest totem pole, and lots more. Cross lots of states off your bucket list and experience incredible sights along the way. Read on for the full scoop on the iconic Route 66!


Illinois- Enjoy some time in the Windy City before you take off for miles on the road. The official starting point of Route 66, Chicago is also one of our favorite U.S cities to explore. You’ve got to stroll through stunning Grant Park, take a photo under the iconic cloud gate sculpture (the one that looks like the bean), and sample Chicago’s favorite eats (deep dish pizza is an essential). Be sure to make a reservation at Monteverde, hands down the best Italian food you will eat outside of Italy.

Missouri- The Route 66 Drive In Theater historic site in Carthage, MO is a must. Pull into one of about 400 parking spaces in this vintage 50’s theatre and you’ve got yourself a pretty perfect Missouri night. Movie snobs, have no fear, there are always two films playing so you can pick your favorite! If you haven’t got enough of the drive in scene, make sure to stop by St. Louis’ Donut Drive-In. Order a few of St. Louis’ best handmade donuts to keep you fueled for the road ahead.

Kansas- Riverton Kansas’ famous Eisler Brothers old general store is as cute as they come. The store essentially hasn’t changed since 1925, so it’s a true step back in time. Relax with a coffee on the porch, grab a sandwich for the road, or buy your friends back home some Kansas souvenirs. You’ll only drive through Kansas for about 15 miles, but the pit stop will make you fall in love with this quaint state.

Oklahoma- Take a little detour in Foyil, OK for the World’s Largest Concrete Totem Pole. Okay, we know what you’re thinking, but it’s seriously cool. The incredible folk art piece, decorated with Native American patterns and designs is 60 ft tall and 30 ft wide. Like every tourist who stops by, you’ve got to take a funny selfie with this towering totem pole. Make sure to pop into Tulsa’s Elote Cafe for ridiculously good Mexican food. We’re not talking velveeta nachos, but housemade sweet corn tamales, vegan quinoa tacos, and slow cooked pork burritos with chili verde. You’re going to love Oklahoma.

Texas- Amarillo’s Texas’ Cadillac Ranch is a modern artist’s dream come true. A group of eccentric artists (it was the 70’s after all) placed 10 graffiti covered cadillacs in a dusty field in Amarillo, Texas. It’s now an iconic expression of art where visitors are welcomed to add their own graffiti. While in Amarillo, check out Midpoint Cafe, a diner exactly halfway between Los Angeles and Chicago. Grab a bite to eat and, of course, some Route 66 memorabilia.


New Mexico- The San Miguel Mission historic site (nerd fact: it’s also the oldest church in the U.S.) in Santa Fe, NM will take you right back to 1710, when it was founded by Indigenous Mexicans. Walk around the mission and you’ll understand the hype over Santa Fe. Need a little R&R after all that driving? Check into Santa Fe’s Ten Thousand Waves Resort for natural hot springs, a renowned spa, and the highest quality lodging and dining.

Arizona- The Grand Canyon is as quintessential an American road trip as it gets. But it’s more than just a place to cross off the bucket list, this national park is a stunning natural beauty that will take your breath away. Whether you hike, swim, raft, or horseback ride through, there’s something incredible to see at every corner. After an exercise filled (and probably hot!) day at the canyon, cool off with a delicious, craft beer at nearby Flagstaff Brewery.

California- Could it get much better than ending your road trip at the famous Santa Monica pier? No. it really couldn’t.  Ride on the iconic ferris wheel, explore by bike,  take a dip in Pacific waters or just walk along and take in that refreshing ocean breeze. They also offer pier yoga classes (trust us, you’ll want that stretch after days in the car). Top off your trip with dinner at Santa Monica’s Cassia, where seafood is as good as it gets.

Sound like the perfect road trip? Let us know your favorite road trip routes in the comments or on social @shetravelswellco