Route 66 Road Trip Guide: Insider Tips on Where to Go, What to See and How to Plan

Article summary:    

This article follows AAA Employee and Members John and Karen Ribbing, as they drive all 2,448 miles of historic Route 66. The feature highlights their cross-country journey from Chicago to Santa Monica, showcasing classic Americana along the Mother Road.

Key highlights from the article include:

• Iconic stops along Route 66: Neon-lit diners, vintage motels and quirky roadside attractions.
• Off-the-beaten-path discoveries: Meramec Caverns in Missouri, the Barbed Wire Museum in Kansas and Blue Hole in New Mexico.
• Insider travel tips: How to navigate the route using travel apps, maps and AAA travel resources.
• AAA Member benefits: Access to AAA Diamond-designated hotels, car rental deals and 24/7 roadside assistance.
• 2026 Centennial of Route 66: Celebrations marking 100 years of America’s “Main Street.”

Navigating America’s “Main Street”

Route 66 begins in Chicago at the corner of Adams Street and Michigan Avenue and stretches across eight states to the sun-soaked shores of Santa Monica Pier.

Based north of Detroit, the Ribbings set off with two close friends, renting a one-way car for the four-and-a-half-hour drive to Chicago.

“We did the entire Route 66 in 11 days—a rush version,” Karen laughs. “It’s recommended to take at least two weeks, but we still hit many highlights.” Their adventure began at the iconic “Begin Route 66” sign in downtown Chicago. “We ran out, took a quick photo—we were double-parked—and then hit the open road.”

As the miles rolled by, the couple marveled at America’s ever-changing landscape. “Starting with Illinois and its cornfields, the scenery slowly shifted to more earthy browns,” John recalls. “It was so cool to see how each state transformed.” Their journey took them through Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and finally California—each stretch offering a unique slice of Americana.

Karen planned nearly every detail herself, relying on travel blogs, maps and the specialized Route 66 Navigation app for real-time guidance. “The app was essential,” she says. “Whenever we used a regular GPS, it tried to reroute us onto the freeway instead of the historic path.” With offline navigation and more than 900 points of interest, the app kept them on track, even through remote areas with limited signal.

The route’s historic hotels

Synonymous with glowing neon signs, mid-century architecture and classic Americana charm, Route 66 is dotted with vintage roadside motels that have become destinations in their own right. For John and Karen Ribbing, these motor lodges were more than a place to rest—they were a chance to step back in time and experience the spirit of the Mother Road firsthand. “I wanted to stay in authentic Route 66 hotels—that was important to me,” Karen says. Together, they crafted an itinerary centered around historic properties that offered a glimpse of what motoring across America felt like in its heyday.

El Rancho Hotel, Gallup, New Mexico

A relic of 1930s glamour, the El Rancho Hotel blends Old Hollywood allure with Southwestern spirit. A favorite of film stars traveling Route 66, the hotel has been carefully renovated, preserving its historic character while offering modern comfort. The Ribbings ended their evening with a nightcap at the hotel’s storied 49er Lounge, soaking in the classic speakeasy ambiance.

Boots Court Motel, Carthage, Missouri

One of the best-preserved motor courts along Route 66, Boots Court Motel radiates 1940s charm. Once famous for its slogan, “A radio in every room,” the lovingly restored property still welcomes guests with that signature touch. “It felt like stepping into the 1940s, with an AM radio playing when you walked in,” Karen recalls. “It was the little details that made you feel like you went back in time.”

Roadrunner Lodge Motel, Tucumcari, New Mexico

At the Roadrunner Lodge Motel, the Ribbings discovered a stylish throwback to the 1960s. Each room features vintage-inspired décor and a custom radio station playing hits and jingles from the ’50s and ’60s—an immersive touch that keeps the nostalgia humming.

Whether chasing neon signs or historic charm, these stops make the Mother Road feel like a journey back in time—without sacrificing modern comforts.

Must-See Detours and Roadside Wonders

When planning their cross-country drive, Karen Ribbing spent hours mapping out detours worth the extra mileage. Her instincts paid off. From underground wonders to quirky roadside museums, the couple’s favorite stops reveal the magic found just off Route 66’s main path.

Meramec Caverns, Missouri

As the Ribbings drove through Missouri, they couldn’t miss the vintage barn ads for Meramec Caverns—a Route 66 icon. Curiosity won and they were glad it did. The guided cave tour offered an awe-inspiring look at vast limestone formations sculpted over millions of years. “It was incredible to see nature’s artistry up close,” says John.

Barbed Wire Museum, Kansas

One of the couple’s most surprising discoveries was the Barbed Wire Museum in La Crosse, Kansas. “We thought it was funny that there was a museum just for barbed wire,” Karen laughs. “But we ended up spending more than an hour there—it was fascinating.” They met a local volunteer in her 90s who shared stories from the museum and Route 66’s past. “You meet these people along the way who carry such incredible history,” Karen adds. “It slows you down and reminds you why the journey matters.”

Blue Hole, New Mexico

A vivid gem in the desert, the Blue Hole in Santa Rosa offered a refreshing pause in the New Mexico heat. “The water was cold—but we all jumped in!” John recalls. “It became a top highlight of our trip.” This deep, spring-fed pool is a popular spot for swimming and diving, known for its crystal-clear water and brilliant blue hue.

Cadillac Ranch, Texas

A bold burst of color on the flat Texas plains, Cadillac Ranch is a must-see stop for anyone traveling Route 66. This whimsical art installation features a row of half-buried Cadillacs, tilted at playful angles, their surfaces layered with ever-changing graffiti. Visitors are invited to bring their own spray paint and add to the ever-evolving canvas that has grown since the installation’s debut in 1974. Cadillac Ranch perfectly captures the free-spirited, quirky charm of the Mother Road, offering a memorable pause and soak in a true piece of roadside Americana.

Discovering the people who make Route 66 unforgettable

Perhaps the most unexpected part of the Ribbings’ Route 66 adventure was the sense of community they discovered along the way. “You’d see the same groups of travelers at the same stops and it was really special to keep connecting and sharing tips and stories,” Karen recalls.

For the couple, the people they met became a highlight of the journey. From service station owners and shop clerks to servers at roadside diners, each encounter offered a glimpse into the unique, storied history of life along America’s legendary highway. “It felt like stepping back in time to an era when striking up a conversation with a stranger was easy and natural,” Karen adds.

These moments of connection brought Route 66 to life, turning each stop into more than just a place to refuel—it was a chance to share stories, laughter and memories that only a road trip on the Mother Road can create.

Miles turned into memories

After 11 days winding through small towns, deserts and neon-lit diners, John and Karen Ribbing finally reached the Santa Monica Pier, greeted by the iconic “End of the Trail” sign. The sense of accomplishment was palpable—not just for the miles they’d traveled, but for the moments along the way.

“Everyone forgot their worries and focused on enjoying the time out there and each other,” says John, a web developer and lifelong road-trip enthusiast. Karen, a small business owner, recalls the thrill of stepping into a bygone world. “It was incredible to see our country like this—so vast, so beautiful. We don’t always stop to admire it enough.” From vintage gas stations and quirky roadside attractions to sweeping vistas of the open plains and desert, the couple savored every turn, every stop, every shared laugh.

Looking ahead to the 2026 Route 66 Centennial, the fun is just beginning. Springfield, Missouri, will kick off the celebrations on April 30, 2026, with a lively festival, followed by a year of commemorative events honoring 100 years of America’s most iconic highway. Start planning your own adventure and experience the magic of Route 66, where the journey truly is the destination.