5 Must-Stop Midwest Roadside Restaurants
We understand why globetrotters are always busy boarding planes, but to explore the Midwest, it pays to get in a car and drive. Of course, you’ll need to eat, so we put together some of our favorite just-off-the-highway establishments for you to visit when you find yourself both hungry and nearby! Then visit us on Facebook and let us know what you think!
The first recommendation, Cafe on the Route, comes to us via a vocal traveler, Theresa Carter a.k.a. The Local Tourist, based in Chicago, Ill. Carter has traveled Route 66 personally and professionally, and is a well-known travel personality in the Midwest.

Cafe on the Route
1101 Military Ave. | Baxter Springs, Kansas 66713 | 620-856-5646
This restaurant in Baxter Springs, Kan., comes dripping with history back to and including a supposed 1876 bank heist perpetrated by none other than Jesse James. The menu is distinctly American, if wide-ranging: from grilled salmon to frog legs to a well-filled selection of steaks. Chef Richard Sanell studied at the renowned Culinary Institute of America, so expect good things here—a real treat.
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The Port Drive-In
419 Calumet Rd. | Chesterton, Indiana 46304 | 219-926-3500
They make their own root beer at this spot in Chesterton, Ind., just off the shores of Lake Michigan and about an hour outside of Chicago. Founded in 1953, it’s changed hands, but continues to be known for hot dogs, burgers and other goodies that come off the always-filled grill here. Per that house-made root beer, get the root beer float. Then, maybe, take a walk?
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Dixie Saloon
401 East Central Ave. | Mackinaw City, Michigan 49701 | 231-436-5449
There’s good food AND a really good story behind this restaurant in Mackinaw City, Mich. Originally built in 1890, age doesn’t keep this from having a nightlife angle to it, including nightly dancing. Located right across from Shepler’s Mackinac Island Ferry, this place has a lot going for it, including tasty ribs, steaks and more.
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Lynn’s Paradise Cafe
984 Barret Ave. | Louisville, Kentucky | 502-583-3447
Down in Louisville, Kentucky, not far off I-65, you’ll find this gem of a breakfast/brunch place both quirky and just downright good. From adaptations of Southern favorites like fried green tomatoes to the ultra-out-there decor that includes a huge number of randomly distributed kitsch, mostly from the 1960’s and 70’s. It’s Southern cooking with an edge and Southern hospitality in abundance at Lynn’s Paradise Cafe.
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Shapiro’s Downtown
808 S. Meridian St. | Indianapolis, Indiana 46225 | 317-631-4041
This well-run deli in Indianapolis, Ind., has been in operation since 1905 and the locals make it a regular stop and the first place they take visitors to town. It’s run like an old-school cafeteria, so pick and choose with strong consideration going to the corned beef sandwich, which is legendary and deservedly so. Also, the desserts. You must try the desserts…and it’s probably a good idea to share—or not.
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