How to Plan a Fly by the Seat of Your Pants Road Trip

In October I embarked on a cross country road trip with my dad. This Southern California girl was moving to Upstate New York (WAY upstate, Frances Houseman vacationing at Kellerman’s upstate) for a year to invest in a relationship with my dad, who I met in October 2012. In the weeks leading up to this adventure, we barely had a plan for the route. In reality, ‘barely had a plan’ is a generous exaggeration. There was a nebulous concept of Los Angeles to New York that never quite seemed to flesh itself out despite countless brainstorms in the months leading to departure day.

Road Trip | Route 66My typical approach to traveling involves purchasing at least two travel guides, then poring over them with color coded highlighting and matching post-it tabs. This compulsive planning instinct (e.g., my approach to packing) was nonexistent. I suppose I was distracted and focused on other aspects of the move (saying goodbye to friends, finding an apartment, sorting through ceramic roosters, booking a moving company, and packing) that I never quite got around to perhaps the most important piece: how I would get myself from here to there. What I discovered is that a little adventure and spontaneity allowed for a memorable, once in a lifetime opportunity to travel Route 66 with my dad.

Google to the Rescue

As the panic began to descend I fled to the warm embrace of Google, which rarely fails me. I stumbled upon the beyond helpful Road Trip USA and its detailed descriptions of a bunch of classic cross country travel routes (like the Oregon Trail, Appalachian Trail and Pacific Coast).

Route 66, among the options described, is a road trip by which I’ve always been fascinated. Growing up, my mom daydreamed about driving Route 66, and went so far as to get AAA TripTik maps created. I remember spending many hours with her, studying the maps and planning our pretend Route 66 journey. These memories, combined with Route 66’s rich history, seemed like a perfect inspiration for this journey with my dad. Route 66 wouldn’t get us all the way to New York, but would get us at least to St. Louis or Chicago. We were on to something… Route 66 it was!

Is There an App for That?

With just two days until departure, there was no time to browse through book stores, place an online order, or visit AAA for comprehensive travel information about Route 66. I needed something quick and easy!

Road Trip | Route 66 AppI hunted through the App Store and discovered Road Trip 66 and at just $0.99 it was perfect! The app covered all the roadside attractions, ghost towns, history, landmarks, restaurants, and hotels along the way. Plus it included turn by turn directions and maps, and allows you to bookmark sites of interest along the way. With the app downloaded, away we went!

Roadside Discoveries

With few concrete stops planned, we meandered across the country with the Route 66 app ensuring that we didn’t get too lost. We explored the country slowly, while stopping at anything that looked interesting. It was truly a fly by the seat of our pants road trip, and I can’t imagine having done it any other way. Here are some highlights of our roadside discoveries.

Roy’s Motel and Cafe

Roy’s, in the ghost town of Amboy, California, was a favorite stop for its perseverance and googie architecture. Opened in 1938, Roy’s typifies the steady decline experienced by the towns along Route 66 as they were bypassed by more developed highways. While you can get gas here, the cafe and motel are long closed. In 2005, the entire town of Amboy was bought by one guy who enthusiastically hopes to preserve this section of Route 66. This is no easy task. On the history page of Roy’s website, the lone 2006 accomplishment simply states, “Roy’s is selling bottled water again.” Despite its failed Kickstarter campaign, perhaps one day that sign will be restored to its 1959 glory!

Road Trip | RoysNeon Signs

Neon signs served as attention getters for businesses along along Route 66, particularly in California, Arizona and New Mexico. Some have fallen into disrepair while others have been lovingly restored. Check out some of the amazing neon signs along Route 66, some in better shape than others:

Road Trip | Route 66 Neon SignsCars of Route 66

While I was most fascinated by the midcentury neon, my dad knew every car on the trip and taught me all about the various cars we saw along the way. It was a great opportunity for us to share our passions.

Road Trip | Cars of Route 6

Map of Many Visitors

Map inside the Hackberry General Store, a Route 66 souvenir shop and convenience store, pinpointing the many places from which visitors travelled.

Road Trip | MapWigwam Village

Wigwam Village #6, built in 1937, is one of the many reasons I find Route 66 so fascinating. An embarrassing example of cultural appropriation, Wigwam Village is also a uniquely midcentury roadside attraction. While shaped like teepees, the architect liked the sound of the word wigwam better and built seven of them in Kentucky, Alabama, Arizona, Louisiana, Florida and California.

Road Trip | WigwamCadillac Ranch

Cadillac Ranch, one of the strangest sights along Route 66, consists of 10 Cadillacs that were buried in a cow pasture as an art installation in 1974. Each car has dozens of layers of bubbly thick paint, along with a stream of visitors bringing more spray paint to add to the graffiti. Unfortunately, people leave the paint cans strewn around the field.

Road Trip | Car with Spray PaintSt. Louis

St. Louis was our last Route 66 stop before heading east to avoid a Chicago snow storm. We were so busy checking out the scenery, I only managed to get one pic with my dad during the entire trip. Here we are below the St. Louis Gateway Arch. As a side note, If you are ever in St. Louis be sure to stop by The Future Antiques for a mind blowing selection of midcentury furniture and accessories.

Road Trip | St. Louis

Open Road

Despite so many fun road side attractions to check out, some of our favorite memories involved taking in the scenery of the open road.
Road Trip | Open Road

Happy road tripping!

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