Where is Route 66 in St. Louis? Two Missouri highways, 366 and 100, claim to be the old Route 66. Why? Because it changed over the years. Both have legitimate claims to Route 66 heritage, so let’s talk about the history, how far apart the roads are, and what makes both of them interesting.
There were at multiple alignments of Route 66 through St. Louis from 1926 to 1975, so no wonder it’s complicated. The two major ones are the 1926-32 version, along the modern MO-100, and the post-1932 version, which is approximately MO-366. There was also a bypass route, which served approximately the same function as the modern I-270/I-255 outerbelt today, but it was closer to the city, and all on the Missouri side.
Where is Route 66 in St Louis?
If you want to use the current interstate system for a road trip to approximate the Mother Road that ran from Chicago to Los Angeles, you can take I-55 south from Chicago (or any point in Illinois) across the Mississippi river past the Gateway Arch to I-44 west through St Louis and the rest of its metro area. That route is about halfway between the two routes that the real Route 66 ran through St Louis, and as such, it misses a lot of the remaining interesting things along what used to be the mother road through St. Louis city and county.
There’s some interesting stuff along I-44 southwest of St. Louis, and that tends to get more attention than what’s left of the mother road closer to the St. Louis metro area. There’s a Route 66 state park and visitor center on the site of what used to be Times Beach, near Eureka, along the Meramec River. Keep going southwest to Stanton, and a number of classic roadside attractions still exist, including Meramec Caverns, which bills itself as Jesse James’ hideout and the largest of Missouri’s many caves. It can make for a fun day trip. But if you live in St. Louis, don’t underestimate what’s on the earlier alignments of Route 66.
What is Route 66 called in St. Louis? The Manchester vs Watson controversy
I always heard that the modern Missouri 366, which is called Chippewa Street in the city and changes names to Watson Road at the St. Louis County line, is the old Route 66.
Then, a few years ago, Route 66 signs started popping up along Missouri 100, which is Manchester Road in St. Louis County and much of St. Louis City, before changing names to Chouteau.
Local news stations even ran stories on the controversy. Which one is the real Route 66?
Both.
Route 366 held the Route 66 designation for a longer period of time, around 40 years. But the modern Route 100 was the original Route 66, before the road we now call 366 was built.
Which one looks like Historic Route 66? It’s debatable. You may want to cruise both and decide for yourself. To explore both, I recommend you check out 366 first, then when it dumps into I-44, stay right to take I-270 north. Take I-270 north to Manchester, then go west on Manchester. Be patient. As you get closer to the city, you see less modern suburbia and more nostalgic things. And a lot of the nostalgic stuff is on the south side of the street, so going east puts you in a position to park or turn right on a side street.
The Case for Route 366
In the county at least, Route 366 looks more like the old Route 66. Much of what once lined that road has been torn down to make way for suburbia “progress,” including the Route 66 Park In Theater and the Coral Courts Motel. But some of the other old motels are still there and still look the way they did in the 1960s. A few other attractions are still along 366, especially once you get into the city. Ted Drewes Frozen Custard, for one. The original location for Cardinals Hall of Famer Stan Musial’s restaurant was along this road, but it’s just a doctor’s office now.
Once you get further into the county, you see more and more strip malls where classic Americana once stood, but in the city, you can still get a feel for what the highway was like, with fewer interruptions.
Courtesy Diner, at the intersection of Watson and Laclede Station Road, looks the part of the classic mother road roadside diner. But that location was built in the 2010s. But if you want classic diner food on the mother road, it’s probably your best option in St. Louis County.
The Case for Route 100
Route 100 has its moments but has lost much of what it once was to urban renewal, especially on the stretch named Chouteau, and while parts of Maplewood are delightful, once you get much west of there, it turns into positively generic suburbia. Now, if you’re going to check out Maplewood, when you get to the intersection of Manchester and Big Bend, at least look south. Kalb Electric, just south of Raising Cane’s Chicken Fingers, has been there since 1909. There aren’t many survivors that old along Route 66 through St. Louis. There was a time when all of St. Louis looked like that.
The south side of Route 100 through Maplewood looks more authentic than the north side. For some traditional nostalgic food, check out Tiffany’s Diner and Strange Donuts, both at the intersection of Sutton and Manchester.
Once you get into the city, Chouteau is still an interesting road. Sadly, the iconic Brains 25 cents sign is long gone, but that was on Chouteau. The 1950s-era fighter jet at Chouteau and Cardinal has a story, even if it hasn’t always been there. You won’t miss it. And deeper into the city, there’s the late, great Eat-Rite diner, which is almost as old as Route 66 itself. By the time you read this, a diner may be operating there again. I hope so.
If you want to go the other direction, Route 100 runs to Gray Summit, where it runs into I-44, where you can pick up Route 66 to Springfield, or Oklahoma, or points beyond.
David Farquhar is a computer security professional, entrepreneur, and author. He started his career as a part-time computer technician in 1994, worked his way up to system administrator by 1997, and has specialized in vulnerability management since 2013. He invests in real estate on the side and his hobbies include O gauge trains, baseball cards, and retro computers and video games. A University of Missouri graduate, he holds CISSP and Security+ certifications. He lives in St. Louis with his family.