The reason I have an eBay account is because of Route 66. One day about half my life ago, I went to the three-year-old auction site to look for an authentic highway sign from the decommissioned Mother Road.

I had just come off my first cross-country adventure, a six-week post-graduate course of my own design that took me from New Jersey to California on a southern route and back on a mid-continent trek. None of that trip was on Route 66, but I think the high from the adventure was still with me. I was living at home and working for the local newspaper in my first job, but I wanted to be back out on the road. I figured driving Route 66 would be a trip of its own, at some undetermined time in the future.

Twenty-one years later, that time has come.

Why now? Well, why not, for one thing. It’s always been a dream to cruise the old highway. But the main reason is the calendar. I work in baseball, and with Thanksgiving on November 28, it offers one of the longest stretches between the end of the World Series and the holiday, which seemed like a good target date for our arrival in Southern California.

I’ve read that retracing Route 66 from Chicago to L.A. can be done in two weeks, but three weeks is considered the bare minimum to allow for a more leisurely pace to see the sights, take a few detours and spend more than one night in a town or city along the way. And that’s just what we have planned.

Casey and I—a generous portion of it done by Casey—have mapped out a daily itinerary that begins with a 10-hour, 686-mile haul to South Bend, Indiana, to stay with friends. The next morning, we’ll head off early to Chicago to pick up Route 66 at the sign on Adams across from the Art Institute of Chicago.

From there, our tour involves no more than four-and-a-half hours, or about 200 miles, of driving Route 66 in any one day.

We’ll spend two days in Illinois, then two in Missouri. Kansas—all 13 miles of it!—will take a few hours to visit a few sites. Oklahoma will cover three days. The Texas panhandle gets two.

We’ll devote nearly a week to New Mexico: parts of six days, with a full day dedicated to exploring Santa Fe (and involving very little driving). Arizona gets five days, one of which will be spent on a train up and back to the Grand Canyon.

Then it’s the final five days to get across California, with a two-day detour to Joshua Tree National Park and a plan to roll into Santa Monica on the Sunday before Thanksgiving.

We have a deadline to return the rental campervan the next morning, and then we’ll spend the rest of the week with friends around L.A. before flying home. If all goes well.

There is so much to see and do. We’ve been reading, scouring maps and planning for months. Our itinerary is packed, and we know we won’t get to everything. Some days may drag on, and we won’t get to a town in time to visit the museum or stop at a particular cafe. We may need to sleep in one day. It may snow in the mountains. Who knows what the road holds?

There’s also this feeling that the history is disappearing. Route 66 was decommissioned by the federal government in 1984, but it started to fade long before that as towns were bypassed by I-44 and I-40.

A lot of what we’ll be seeing as we’re driving Route 66 are ruins—abandoned gas stations and motor courts, ghost towns—or restored sites freshened up with new paint, signs and other details that serve as reminders … or as museums. I think seven of the eight states—maybe not Kansas—has a dedicated Route 66 museum. I don’t know how many of the motels, businesses and eateries we’ll encounter are authentic, continuously operating remnants of the road’s heyday.

This desire to see things before they’re gone — a fear of missing out — goes back to 1990, when I read about the last season of Chicago’s Comiskey Park. I never got there (my travel budget in eighth grade was limited), but I still wish I had lobbied for a family vacation to the Windy City.

Nine years later, I made sure not to miss Tiger Stadium in its final season, and last year we traveled to Dry Tortugas and Glacier National Parks, conscious of the effects climate change (rising seas for Dry Tortugas, melting glaciers in Montana) may have on the landscape.

Much of Route 66 has been crumbling for 35 years —or more—and the ranks of those who remember traveling on it are dwindling. They’re the ones who have saved what’s left, but how dedicated will later generations be to preserve these relics?

So we’ll go and “see what’s out there,” as James Earl Jones as Terrence Mann said of the corn in “Field of Dreams.” We’ll drive Route 66 “because it’s there,” as George Mallory replied when asked why he wanted to climb Mount Everest.

But one thing I don’t expect we’ll see is a truly authentic U.S. highway shield with the number 66, at least not one outside of a museum. As I discovered on eBay back in ’98, the reproductions are much more plentiful than anything seen by displaced Dust Bowl farmers or postwar baby boomers on a family vacation.

Which is just as well. One of those would be hell to fit into a suitcase for the flight home.