Cruise back to the 50s at the Midwest’s best drive-in diners

Get lost in the 50s at these classic drive-in restaurants…

When the car-craze hit the United States after World War II, no part of the country came down with the car-crazies more than the midwest. After all, this was where those big steel beauties were being built. It should be no surprise then that some of the very coolest drive-in restaurants are in the midwest, many operating just as they did 60 years ago. Here are 5 of our favorites…

Arnold's "Fabulous Fifties" Drive-In (Decatur, Ind.)

We hope you like 1950s music because you’ll get a dose of it at Arnold's Drive-in in Decatur, IN. Arnold’s hosts everything from cruise-ins to Elvis-impersonator nights, so if you’re looking for an escape to the 1950s and 60s, this place with do it for you.


Dari-ette Drive-In (Saint Paul, Minn.)


When you’re in a place like Saint Paul, Minnesota, summer seems to come and go rather quickly… You’d think it would be tough to run a little drive-in up here, but the Dari-Ette Drive In is a 60 year institution up there. Folks mark the opening and closing days on their calendar and the place quickly fills up with families, old cars, and poodle skirts as soon as they turn on the gorgeous neon sign for the season.


Rudy's Drive-In (La Crosse, Wis.)


To appreciate Rudy’s Drive-In, you have to know a little of the 80+ year history of this family-owned business:

Grandpa (Wm.) Rudy opened his first A&W Root Beer stand in Chippewa Falls, Wisconsin in 1933. Four years later, in 1937, he bought an existing root beer stand on the corner of 4th and Vine, which is now the new County Building parking lot. In 1938, he built another root beer stand on the Causeway, which is now the site of Peking Restaurant. The Causeway store was closed in 1945 due to war rationing. In 1939, a root beer/popcorn stand was opened on the corner of 4th and Main street across from the Rivoli Theater.

Grandpa William Rudy was succeeded in business by son Dale who had worked in the restaurants since childhood. In 1979, Dale had the honor of being the first fast food operator to be presented the Wisconsin Restaurateur of the Year Award.

The drive-in at 10th and La Crosse Streets was built in 1966 and remains the last drive-in owned and operated by the Rudy family. The tradition continues, three generations later...with grandson, Gary.

That tradition also includes so many cruise-ins, car shows, and special events, most benefiting charities, that it’s hard to imagine Rudy's Drive In not packed with sweet old cars or motorcycles every night of the summer.


The Drive-In (Taylor Falls, MN)


There’s nothing about The Drive-In that doesn’t scream 1950s. “You'll find carhops in poodle skirts, homemade root beer and old fashioned, hand-packed burgers!” No wonder the Drive-In in Taylor Falls, MN is consistently getting press as being not only one of the best of the midwest, but of the entire country. Their sister location in Grantsburg, WI is just as charming as well. Weekly cruise-ins keep that location filled with classic cars and just the right retro vibe.

Gene’s Root Beer (Anderson, IN)

From the 1950s until the 1990s, Anderson and Muncie Indiana were hotspots for American auto manufacturing with both cities pumping out electronics and transmissions for the “Big 3.” No surprise then, one of the best drive-ins is in Anderson: Gene's Root Beer. Despite the auto business leaving the city gutted, Gene’s has survived as a sweet reminder of a time when the people of the city built parts for Chevrolet then drove their own Chevys down to Gene’s on Friday nights.

Places explored in this article:

This was originally written for Roadtrippers, a great resource for anyone interested in travel.
Want more articles by Austin Coop? Find them here!