Old Route 66

My understanding is that the lore of Route 66 was born before the interstate highway system was built. Afterwards, it became run down and terribly cheesy.

However, it could still be interesting for those reasons.

I lived on it in Waynesville, MO right in the middle of the route you are talking about for more years than I cared to admit. The owner of a company I used to work for did all of ole 66. I personally wouldn't do it just for the "route 66" thing, but here are some other things to do and see like Meramec Caverns.

In most places the fact that they are route 66 is either forgotten or as someone mentioned tourist traps. Very little remains of the historical aspect from what I have experienced. Some town have things like "old settlers day" and the like if you can find some of those it might be ok.

Never done it myself.

Billy Connolly did a TV series where he drives Route 66 from Chicago to LA on his motorcycle

Watch on YouTube

Did Chicago to LA in 2014 over 17 days. For the stretch you're speaking of we did Chain of rocks bridge, gateway arch, Ted drewes frozen custard, Route 66 state park, Meramec caverns, stayed at Wagon wheel in Cuba. Saw the worlds largest rocking chair. Passed by the munger moss motel, Hookers cut and devils elbow. I think there are some old souvenir shops in that stretch too.

LINK