For many, traveling Route 66 was a bucket-list trip, and I’d dreamed of hitting the Mother Road for many years. I was thrilled to be turning my dream into a reality when my brother-in-law and I signed up for a guided Route 66 car caravan with Two Lane America in 2020, the same year I turned 66.

Now that I was signed up for the trip of a lifetime, I knew I needed the perfect car: comfortable, reliable, and fun. Having been a Mopar fan since I was 19, I knew what I wanted and found it: a bright red 2016 Hemi Challenger with a white and black interior.

With the perfect car in my grasp, I couldn’t wait until our trip. Then, of course, COVID happened. Instead of 66, I spent two summers falling in love with my Challenger driving around town. Some of the options I really liked were the air conditioned seats, the quiet cabin (even at high speeds), and the “speed lady” who reminds you when you are exceeding the speed limit by a certain amount.

That all left me itching to get the car on Route 66. Fast forward to September 2022; we met up in Chicago, with about 20 other enthusiasts, and you could feel the excitement as we went to our welcome dinner at the Exchequer Pub, known for Chicago Style Pizza and at one time frequently visited by Al Capone. I even got my picture holding Al’s “Tommy gun.” Pretty cool.

We all retrieved our vehicles for an 8 o’clock start, even though it was raining, big smiles all around as our adventure began. As we made our way out of Chicago I knew this was going to be a great experience. At our first stop, an old dinner, I noticed a 2009 Challenger in the parking lot. It turns out they were joining us, another Mopar buddy! We spent many hours over the trip discussing our cars and how reliable they were.

It would take too much time to tell you every place we saw on the Mother Road in our 13-day adventure. One thing for sure is Route 66 is packed full of amazing photo opportunities, especially if you have a good looking car. From restored filling stations dating back to the 1920s to quaint roadside attractions and murals to vintage brick sections of Route 66, the whole trip feels like a big photoshoot.

Some of my favorite spots were going to the top of the Gateway Arch, spray painting the cars at Cadillac Ranch, touring Santa Fe, the town of Oatman (where wild burros roam free), the detour to the Grand Canyon, and the Santa Monica Pier. For us, driving Route 66 was only part of the fun. Meeting the people that own the mom and pop places along the way and hearing their stories of working to revitalize Route 66 were truly inspiring.

Another added bonus was meeting the people in our guided caravan group, many of whom we are still in touch with today.

Not only were you experiencing amazing sites and experiences, you were experiencing it with newfound friends, a major perk of doing the trip with a guided caravan company.

Compared to planning the trip on our own, Two Lane America also made sure we saw a slew of things we probably wouldn’t have seen on our own like the Oklahoma City Bombing Memorial or the Devil’s Rope Barbed Wire Museum.

The tour company even arranged for us to have lunch on stage at an opulent Route 66 theater in Miami, OK, a true hidden-gem.

All we had to do each day was hop in, put our foot on the gas, and have a great time. The hotels, many of the meals, and all the experiences, whether it be a visit to an old diner or a national park, were taken care of.

The Challenger, of course, performed flawlessly. It had plenty of space for the huge number of souvenirs we bought, was comfortable, and even averaged 30 MPG over the course of not only the 2,400 miles of 66 but the over 6,600 total miles we put on it driving across the US that fall.

Speaking of souvenirs… If you do a trip like this, plan on buying plenty! Our group alone bought over 50 t-shirts, 20-plus hats, 40 license plates, 5 shot glasses, and 3 flags, all to support 66 in a small way. In the end, my guided Route 66 tour was everything I’d hoped it would be and more, especially since I was in the perfect car for it.

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