Over the decades, the highway has attracted American Dreamers of various circumstances and exigencies. In the first half of the 20th century, they piled their families into jalopies to escape the Dust Bowl or to find work during the Great Depression. During World War II, soldiers followed the road in the name of service and duty. In the mid-century, liberated motorists embraced the car culture, and later the counterculture. More recently, nostalgia-seekers have boarded Route 66 to travel back in time.

This year marks two significant anniversaries: The Mother Road turns 90 and Bobby Troup’s anthem, “(Get Your Kicks on) Route 66,” which Nat King Cole recorded, adds a 70th candle to its cake.

[Route 66 road trip: A real-life remix of where to ‘get your kicks’]

What do you get a road that once had everything? A card and a cupcake seemed uninspired. Instead, I opted for a grander gesture: I packed up my birthday wishes and spent two weeks in July driving the route from Illinois to California. In addition, I wrote a remix of Troup’s song, updating the locations in the original with towns that are more than just rhyming devices. The new destinations better represent, and honor, the Main Street of America. Because unless I needed a frozen burrito from a Shell station, I could forget Winona.

I thought I was prepared, but the road quickly dispelled my delusions.

From pre-trip research, I knew that Route 66 was not a straight line; it wriggles and curves like spiral pasta. Highway planners had realigned the road several times between 1926 and 1985, the year it was decommissioned and replaced with five interstates across eight states. Approximately 80 percent of the original road still exists, but signage is spotty. Because of its patchwork condition, I would have to flit between old and new segments, some smooth, others choppy. In addition, distances would take twice as long to cover. Or, in my case, multiply by four: For instance, it took me five hours to travel the 70 miles from Oklahoma City to the Cherokee Trading Post in Geary. The trouble started when I missed a right turn and ended up on the interstate headed eastbound, toward the morning’s starting point. When I finally arrived at the Western store, I beelined for the shoe department and released my frustrations by stomping around in cowboy boots.