2026 Route 66 100 year anniversary - potential tour?

Well, as for an “idea”, I was under the impression Route 66 is historically and technically starting in Chicago and ending in Santa Monica, hence should be driven/traveled from east to west ?

Also, you might want to research the actual routing, etc of it.
My best friend & his wife drove east-to-west following it several years ago, using a +/-20 year old guide booklet about it and various attractions & sites along it, but according to their discoveries, almost half of the attractions/sites no longer existed, not to mention large sections of the original road no longer exist or some that do, are if not impossible, at least difficult to access for any reasonable sense of coherence.
IIRC, they spent 7 or 10 days and she took +/-10K photos between start & finish.

Might be one of those romantic ideas that often sound better on keyboard or paper than in practice.

 

I will be doing some of Route 66 in May 2026. Starting in Carlsbad and heading east to about Oklahoma. I'll be driving my little Boxster to an event in the Smoky Mountains. Should be fun.

 

If you get traction on putting this event together, would love to be a participant

 

As someone with a few hundred thousand miles behind the wheels of countless vintage cars, including numerous multi-thousand mile drives/road trips all around the continental U.S. in past 40+ years, I agree that (interesting) cars, especially older ones are best enjoyed by driving them extensively & as often as possible and while I wholeheartedly hope you’ll be able to do and enjoy your Route 66 experience, I just wanted to offer comments & suggestions based on aforementioned personal experiences, both mine & my friends.

For example, some here may not be aware that literal driving the historic Route 66 from one end to another, regardless of direction of travel, is or will be pretty much impossible today as vast sections of it has been either erased, redirected or replaced with conveyor belts known as Interstate* highways, bypassing some of the few still existing attractions, cities, towns, places of interest, etc associated with the original Route 66.

As for “compelling reasons” to drive vintage cars, I’ve never had a problem to come up with them easily (please see my first paragraph), but I prefer to do mine alone, especially long distance travel, so I can be free of any constraint's group touring/travel can present. I learned that the hard way during my first across the U.S. (3000+ mile) road trip 41 years ago, driving/traveling with two friends, each of us in our own vintage cars we had bought just a couple of weeks earlier.

In fact, just a couple of days ago, my wife & I finished yet another wonderful 10-day, 1500+ mile road trip adventure around southern & central California, reaching nearly 8000 ft. elevations, experienced temperature changes from mid-30’s to mid-80’s and weather ranging from pouring rain storms to scorching sun, etc, but thanks to the navigation & preliminary planning by my wife, managed to do most of it on scenic back country roads & secondary highways on the coast, desert, farmlands, forests, mountains, etc while driving a 93 year old open wheel Roadster with +/-75 year old drivetrain & general technology (allowing for relatively “comfortable” 65-70 MPH highway speeds), 6V electrical system with no heater, side windows or other creature comforts, etc.

*I don’t know about others here, but I’ve always found Interstate highways along with Belt-, Free-, Tollways & Turnpikes, etc intended for commercial and commuter traffic to be the most boring way to travel in any road going vehicle, especially in ones designed and/or intended for enjoyment & pleasures of driving.

 

Then it sounds like this isn’t the trip for you.

Carry on…