When it comes to iconic road trips, it doesn’t get any better than Route 66. Or so I’d hoped when my husband and I packed up our three teenagers in a rented Suburban and drove over 5,000 miles from our home in Ohio across the country to California and back via the Mother Road. Where else can you find more roadside attractions, diners and mom and pop motels dotting the landscape than you can count?

Visiting Roadside Attractions along Route 66 with Teens

Photo Credit: Tonya Prater / Ohio TravelingMom

Exploring Roadside Attractions and more along Route 66 with Teens

Will Rogers Highway. Main Street America. The Mother Road. I don’t care what name you know it as, exploring Route 66 had been on my bucket list for as long as I could remember. When my family decided to make a trek from Ohio to Hollywood, California, I knew my opportunity to explore the historic highway had finally arrived.
I imagined an epic road trip where we’d get our kicks on Route 66, and spend the days viewing fun and quirky roadside attractions, eating at old time diners and resting our heads at mom and pop motels. My family had something else in mind.

With five days set aside to reach our target destination, we didn’t have time to fully explore all the sights and towns along Historic Route 66, so we picked up the route outside St. Louis instead of Chicago. Even though we missed a portion of the highway, the closest we got to eating at a diner was at Denny’s in a truck stop, and I could not convince my family to sleep at a mom and pop motel until we were no longer on the Mother Road, we did manage to see some amazing sights and roadside attractions. Oh the roadside attractions! So many to see and yet so little time, of which my family was thankful. Try as I might, my affinity for the fun and quirky attractions has yet to rub off on my offspring.

Getting Started along Route 66

A quick stop at the Visitors’ Center of the Route 66 State Park just outside St. Louis will arm you with brochures and ideas of places to stop along the route. There is also a free museum with memorabilia and information on the history of Route 66 and if you need to stretch your legs, you’ll find hiking trails to explore.

You'll find plenty of roadside attractions along Route 66 like this one in Missouri that was once the world's largest rocking chair.

Photo Credit: Tonya Prater / Ohio TravelingMom


Our first official roadside attraction was The World’s Largest Rocking Chair in Cuba, Missouri was fun, though my teens were disappointed that they weren’t allowed to rock in it. This attraction has now been dethroned, as a larger rocking chair has claimed the World’s Largest title in Casey, Illinois.

The Outdoor Symbolic Memorial at the Oklahoma City National Memorial is moving during the day and night.

Photo Credit: Tonya Prater / Ohio TravelingMom

The Oklahoma City National Memorial was an easy side trip and well worth the short detour from Route 66. We didn’t have time for the museum, preferring to linger at the Outdoor Symbolic Memorial. This is one attraction that you can stop at day or night, as the 168 chairs representing those who lost their lives in the bombing are illuminated after the sun sets and available for viewing 24 hours a day, 7 days a week except Thanksgiving and Christmas.

Texas-sized Roadside Attractions along Route 66

The Giant Cross in Groom, Texas, was once the largest in the United States until a nearly identical one was constructed in Effingham, Illinois. Surrounding the base of the cross are a series of bronze statues depicting Jesus’ last days on Earth. There is also a gift shop and a fountain where you can reflect and pray.

The Leaning Water Tower Roadside Attraction in Groom Texas

Photo Credit: Tonya Prater / Ohio TravelingMom

Nearby, you’ll see The Leaning Water tower, also in Groom. It isn’t a stop that requires a great deal of time, but it is fun to see and if you’re one of those families that loves fun photo ops, you could easily take a photo of a member of the family pretending to push the water tower over.

My teens really wanted to try to eat a 72 oz. steak at the Big Texan in Amarillo, but the only roadside attraction we managed to see in this town was Cadillac Ranch. Believe me when I tell you they weren’t at all thrilled by this stop, even though we were armed with spray paint ready to leave our mark on the attraction. Where else is it legal to actually deface someone else’s property?

The Conoco Station roadside attraction is located in Shamrock Texas

Photo Credit: Tonya Prater / Ohio TravelingMom

We passed through many other small towns, stopped at more roadside attractions and finally made our way to the Conoco Station in Shamrock, Texas.  If you’ve watched Disney’s “Cars,” then you probably know why I felt a stop at this icon was important.

To get a break from roadside attractions, we stopped at the Petrified Forest to stretch our legs.

Photo Credit: Tonya Prater / Ohio TravelingMom

Take a Break from Roadside Attractions along Route 66 to Stretch your Legs

The Painted Dessert and Petrified Forest not only offered spectacular views, but a great stop for my teens to burn off some pent up energy after our long road trip.
I had originally planned to sleep in a teepee at the Wigwam Motel in Holbrook, Arizona, but just didn’t time things right. Instead, we continued on to another detour — this time heading to the Grand Canyon.

The Grand Canyon was amazing and though it was not originally on the list of places that we would see on our trip out west, it easily became a favorite stop for my entire family.

Our journey along Route 66 came to an end at the Santa Monica Pier in Los Angeles, but that’s only the beginning for this traveling family. This year my husband and I hope to visit the rest of the U.S. via road trips and I wouldn’t be disappointed if one of those trips lead us back to Main Street of America.

Roadside Attractions along Route 66 that are fun to explore with teens.