A honeymoon on the historic Route 66: Chicago to St. Louis!

A traveling honeymoon!

Route 66. Chances are you have traveled on America’s first iconic highway at some point in your life. Along the path of this beautiful & long road, you will find asphalt, gravel and even the original brick.  From Chicago, IL. to the Santa Monica Pier in Southern California, buckle up. This is going to be the first of a series about hidden gems you will come across when you travel along this historic national treasure.

Illinois alone has 400+ miles of Route 66, with a mix of diners, lots of restored gas stations, museums, and murals. Take your time on this drive. It’s worth it.

We start with Chicago, IL. Why? Because that’s where Mother Road starts, it only makes sense.
If you want to drive the entire thing – go for it! Maybe it’s on your bucket list or maybe your (grand)parents did it and you want to recreate it. Do it!! I have met lots of couples that have enjoyed the journey.  Just remember the one rule: Take pics!
Now let’s get into it!

There are so many things I could put on this list. But, for the sake of small blog, I will try to limit it.
From Chicago to Joliet:
1. Chicago is clearly the 1st point to start at, as this is home of the “Route 66 Begin” sign.  It is located at The Art Institute of Chicago, between Adams St. and Michigan Ave. It’s easily accessible for photos, but don’t miss it. It may be a bit hard to find. The last I knew, it was covered in stickers. Add your own, responsibly of course.
Before you start your journey, eat at Lou Mitchells. It’s a classic old school- diner; nothing fancy, but it’s covered with black and white photos of the route 66 travelers, and the photos tell the stories.

2. There are other stops in the Chicago area, but if you want to get on the road and start your journey, start with the Route 66 Park & Route 66 Experience (Joliet) – Signage, murals, and maps. Even the web address for this attraction is super helpful. From site maps and travel tips to state-by-state attractions and itineraries!
https://route66roadmap.com/attractions/route-66-park-in-joliet-illinois/

From Wilmington to Pontiac:
3. Polk-a-Dot Drive-In (Braidwood) – Fun 1950s-style diner with Elvis, Marilyn Monroe, and Blues Brothers statues. Just knowing there is a 50s-style diner out there with an Elvis statue should make you want to stop. But if that’s not your thing, maybe their famous chili cheese fries will make you stop. Make sure to take a picture using their payphone that still hangs on the wall.

Now, let this be the time in the story that I remind you there are a ton of retro Route 66 gas stations along the road as well. You will find several between the points of Chicago and California. I will highlight the great ones.

4. Pontiac Route 66 Hall of Fame & Museum (Pontiac) – Huge collection of memorabilia, plus the world’s largest Route 66 shield mural. Plainly, if you are going to take the trip, then stop and take the pictures.  The mural is huge and takes up the entire side of an old brick building.



From Bloomington to Lincoln:
5. Keep heading south – you’re going to hit Dixie Truckers Home (McLean) – One of the first truck stops on Route 66, open since 1928. If you’re looking for cheap, good homestyle meals, this is the place.  I went there a lot as a child, but the last two times I have been was when dad took me in 1999 and when I took a friend there in 2010. Both times it looked the same from the 80s, and I really doubt it has changed much, if at all.

6. Just 15 more minutes from the truck stop and you’re in Lincoln, IL. If you are interested in “World’s Largest” then here is your chance to stop and see the Railsplitter Covered Wagon (Lincoln) – The world’s largest covered wagon, with an Abe Lincoln statue reading a law book inside.

Springfield:
7. Starting off strong with my town’s Cozy Dog Drive-In – Birthplace of the corn dog on a stick. More commonly referred to as Corn Dogs now, the battered hot dog can’t get any better than it does here. And unlike Chicago, it’s perfectly acceptable to put catsup on your dog. No one will judge! And, on a side note, one member of this famous family turned down the Pixar film “Cars”, when he was offered the role as the Volkswagen.

8. Next up, Route 66 Drive-In Theater – A restored 1950s drive-in still showing movies! No speakers next to the car (at this drive in), but no problem! All you have to do is tune into the radio station and viola – there’s the sound!! Don’t forget your concessions and let the kids burn off some energy in the little playground they have. It’s a perfect nostalgic night.

9. Now, just next to the Route 66 drive in is my very own Pole Barn Chic Events! I can’t not add this – the coincidence is just too good! The old highway stops at my mailbox. Literally. Located on the historic Stonegate Farms, the PBC Venue is a stunning wedding venue that welcomes everybody. Look us up – not only are the grounds amazing, but our photo areas are beautiful, and the staff is great! Stop by anytime 8-4. We can guarantee you’ve never seen a pole barn like this! Pictures does NOT do this venue justice. Trust me.


Springfield to St. Louis:
10. Though I have never seen it, the reason behind it is nice. If your fancy is tickled, make time to stop at Our Lady of the Highways Shrine (Raymond) – A roadside shrine erected for traveler safety.

11. And I will end the “Chicago to St. Louis” blog with this last stop in Litchfield, IL.  Ariston Café (Litchfield) – One of the oldest restaurants on Route 66, family-run since 1924. This restaurant has changed ownership thru the years, but one thing has always remained the same. That old restaurant feeling. Not old as in ran down, but old as in an old school restaurant that makes you think of meatloaf. And bonus -- still has a salad bar!


Pole Barn Chic is locally owned and operated. We hope to encourage engaged couples to consider choosing a locally owned wedding venue. We go to great lengths to exceed expectations, and you will find that locally owned wedding venues have far less turnover and that leads to better communication! We love shouting out and supporting our locally owned wedding venue and wedding business colleagues. Here are a few locally owned wedding venues across the US:

Events by Bliss Barn – eventsbyblissbarn.com
Talula Mesa – talulamesa.com
Green Clover Farm – greencloverfarmohio.com
The Venue at Murphy Lane – thevenueatmurphylane.com
Notting Hill Farm – nottinghillfarm.com

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10 Midwest Roadside Attractions to Visit