Your Ultimate Guide (Including 6 Must-See Stops) To Route 66

Would you like to connect with other like-minded 40+ women and make new friends? Then join our private Facebook group, The Girlfriend Social Club, today. You’ll love it!

Is there anything more American than Route 66? From John Steinbeck to Chuck Berry, Cars to Thelma & Louise, it’s our nation’s most celebrated highway. Starting in downtown Chicago, the “Mother Road” passes through eight states and a total of 2,448 miles before ending in Southern California. For thousands of Americans who drove west during the Dust Bowl era, it symbolized mobility, opportunity and the search for a better life.

In 2026, the historic route turns 100 and festivities are planned at dozens of stopping points along the way (see details at route66centennial.org). But you don’t need to wait to discover the joys of the Mother Road. Whether you head out for the weekend or plan a full-scale road trip, here are six places to get your kicks on Route 66.

Start at the Beginning: Chicago

Start your adventure at the “Begin Historic Route 66” sign in the middle of downtown, right in front of the Art Institute of Chicago. Across the street, the Palmer House Hilton Hotel has a “Get Your Kicks” package that includes luxury accommodations plus cocktails at Potter’s Bar, a Route 66 Spotify playlist and the hotel’s signature brownies for the road. Other highlights include Lou Mitchell’s, an old-style diner once known as the first stop for travelers heading west, and Jackson Boulevard, a part of the original route. You can also see “America’s Highway” from Skydeck Chicago, the highest observation platform in the United States — on a clear day, the view stretches for 50 miles.

Birthplace of Route 66: Springfield, MO

In 1926, officials met in Springfield and proposed the name “U.S. Route 66” for the Chicago-to-Los Angeles road, earning the city its title as the “Birthplace of Route 66.” The iconic destination is also a great spot for a girls’ getaway. Enjoy brunch at The European, a stylish café with lush greenery and pastel interiors or the veggie-forward Sleepy Opossum Café. Then explore the immersive Wonders of Wildlife National Museum & Aquarium or stroll historic Commercial Street for boutique shopping and local finds. When the sun goes down, toast your friendship at the rooftop bar of the sleek, modern Hotel Vandivort or catch a flick at the Gillioz Theatre, a restored 1926 movie palace that hosted vaudeville acts in Route 66’s heyday.

Middle of the Road: Oklahoma City, OK

As Nat King Cole, Chuck Berry and John Mayer famously sang, the capital of Oklahoma is an “oh, so pretty” stop on Route 66 — it’s also right in the middle of the Mother Road. Don’t miss the National Cowboy & Western Heritage Museum, America’s premier institution of Western art and culture; the Myriad Botanical Gardens, with 15 acres of grounds and a stunning crystal conservatory that is free and open to the public or the dining, shopping and canal tours of the revitalized Bricktown Historic District. Spend the night at the newly restored Skirvin Hotel, which has been welcoming politicians, speculators and celebrities of all stripes since 1911.

Retro Route: Albuquerque, NM

This Southwest city boasts the longest urban stretch of the original Route 66 still in existence, with 18 miles of glowing neon signs, vintage artifacts, retro motels and honky-tonk dives. Follow Central Avenue through Old Town — stopping to explore the city’s oldest building, the Church of San Felipe de Neri — to the Nob Hill neighborhood, with its eclectic mix of art galleries and live music venues. Then, take a short detour to the Indian Pueblo Cultural Center or enjoy breathtaking views from the Sandia Peak Tramway, North America’s longest aerial tram ride. Spend the night at the charming Hotel Parq Central, a restored building that once served as a hospital for employees of the Santa Fe Railway Company.

The Gateway City: Flagstaff, AZ

Located at a cool 7,000 feet above sea level, this mountain town is ideal for exploring Arizona’s majestic canyons and pristine pine forests. Known as the “Gateway City” for roadtrippers heading west, it’s also one of the best-preserved Route 66 towns. Stop by the Flagstaff Visitor Center and Historic Train Depot, where you can learn about the transition from train travel to automobile road tripping that began in 1926. Then explore local gift stores, shop for Native American jewelry and souvenirs and enjoy some of the region’s award-winning craft beers. Make sure to visit the Museum Club, a Route 66 landmark that used to be Arizona’s largest log cabin; it’s now a premier country music venue that hosts national acts as well as regional bands, with a large wood dance floor and two full-service bars. Just outside of town, the Little America Hotel is a cozy and welcoming place to spend the night.

End of the Trail: Santa Monica, CA

After more than 2,400 miles of driving, it’s no wonder early travelers viewed the city of Santa Monica — with its mild weather, white-sand beaches and stunning views of the Pacific Ocean — as the promised land. It’s also known as the “End of the Trail” for Route 66 because it’s the place where the Mother Road meets the Pacific. Visit the Santa Monica Pier to celebrate the end of an epic journey, take a selfie by the historic “End of the Trail” sign, ride the world’s only solar-powered Ferris wheel or bicycle down scenic Ocean Avenue. Cap off your visit with a cocktail at The Living Room, the beachside lounge of Shutters on the Beach hotel.

Have you ever driven the Mother Road? Let us know in the comments below.