The All-American Road Trip: A Journey Down Route 66

Start: Chicago, Illinois

Kick-off at the "Windy City."
Route 66 begins its epic journey at the corner of Adams Street and Michigan Avenue in Chicago. Before you hit the road, indulge in deep-dish pizza at Lou Malnati’s or grab a classic Chicago-style hot dog. A quick detour to Millennium Park to snap a selfie with "The Bean" is almost mandatory. For a nostalgic start, visit the Art Institute of Chicago or hop on a vintage trolley tour.

Pontiac, Illinois: Murals and Museums

Small-town charm meets big artistic vibes.
Just a couple of hours into your journey, Pontiac welcomes you with its colorful murals and the Route 66 Hall of Fame Museum. The museum is a treasure trove of vintage signs, photos, and stories from the heyday of the highway. Don't miss the life-size mural depicting a classic '66 road scene — it’s Instagram gold.

St. Louis, Missouri: The Gateway to the West

Barbecue and beer with a side of history.
Cross the Mississippi River into Missouri and you’ll land in St. Louis, home to the iconic Gateway Arch. Take the tram to the top for stunning views, then reward yourself with some local barbecue. Pappy’s Smokehouse ribs are legendary, and a frosty beer at Schlafly Brewery is the perfect pairing. While here, swing by Ted Drewes for their frozen custard – a Route 66 tradition.

Carthage, Missouri: The Route 66 Drive-In

A retro detour under the stars.
Head further west to Carthage, where you’ll find the 66 Drive-In Theatre, a functioning drive-in that harks back to the golden age of cinema. Grab some popcorn, settle into your car, and let the glow of the big screen transport you.

Tulsa, Oklahoma: Oil Boomtown

Art Deco delights and cowboy culture.
Tulsa boasts one of the most well-preserved stretches of Route 66, complete with vintage motels and neon signs. Dive into its Art Deco heritage by visiting the Philcade Building or the Boston Avenue Methodist Church. For a taste of cowboy culture, check out the Gilcrease Museum, or get hands-on with some live music at the historic Cain's Ballroom.

Amarillo, Texas: Bigger Is Better

The Lone Star State does it big.
Amarillo offers a mix of kitsch and cowboy. Start at Cadillac Ranch, where you can spray-paint graffiti on upturned cars — an evolving art installation that’s pure Texan quirk. Hungry? The Big Texan Steak Ranch dares you to tackle its 72-ounce steak challenge. If you’re not up for it, their regular menu is just as satisfying.

Santa Fe, New Mexico: Southwest Splendor

Artistic soul and adobe charm.
Detour off the main route to visit Santa Fe, a mecca for art and culture. The Georgia O’Keeffe Museum is a must-see, and the city’s Pueblo-style architecture provides endless photo opportunities. Wind down at the Santa Fe Plaza with some local tamales or green chile stew.

Flagstaff, Arizona: Gateway to the Grand Canyon

Stars above and wonder below.
Flagstaff is a hub for outdoor enthusiasts and stargazers alike. Take a day trip to the Grand Canyon or explore the nearby Meteor Crater. In town, the Lowell Observatory offers guided stargazing events that are out of this world. Don’t leave without trying some local Navajo tacos.

Kingman, Arizona: Route 66 Museum

Dive into the highway’s history.
Kingman is a love letter to Route 66. The Arizona Route 66 Museum here showcases the road’s storied past, from Dust Bowl migrations to its status as a pop culture icon. It’s a great place to reflect on how far you’ve traveled.

Santa Monica, California: Journey’s End

Where the road meets the ocean.
Your adventure culminates at the Santa Monica Pier, where the "End of the Trail" sign proudly stands. Dip your toes in the Pacific Ocean, grab a churro, and ride the Ferris wheel to celebrate completing this epic journey. The bustling pier and nearby Third Street Promenade are perfect for a leisurely end to your trip.

Tips for the Road

• Timing is everything: Spring and fall offer the best weather, with fewer crowds and cooler temperatures.

• Stay flexible: Some attractions may require detours, so build extra time into your schedule.

• Fuel up frequently: Gas stations can be sparse in some stretches, so don’t let your tank drop below half.

• Soak it in: The beauty of Route 66 lies in its surprises — quirky roadside stops, breathtaking landscapes, and friendly locals. Take your time and savor every mile.

Route 66 is more than a road; it’s a rite of passage. Whether you’re chasing nostalgia or simply exploring America’s heart and soul, this journey promises memories that will last a lifetime. So, start your engines and let the Mother Road guide you to adventure.