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Midwest Time-Warp Trips

Enjoy a fun blast from the past at the region's best diners, drive-ins and other spots that celebrate a more carefree era.
  • Retro in the Midwest

    The decades seem to dissolve at places throughout the Midwest: diners with doo-wop on the jukebox, soda fountains with chrome fixtures, theaters that show two movies for less than $10.

    We go to these retro spots for the charm. We go for the history. But mostly we go in search of a feeling we thought we'd lost. And we find it--in the sweet mingling of root beer and vanilla ice cream, in the sparkling smile of a waitress on roller skates, or in the silvery flicker of a movie in an open field on a hot summer night.

    Click ahead for our picks of Midwest drive-in theaters, drive-in restaurants, soda fountains, diners and other spots where you can turn back the clock.

  • Favorite Midwest drive-in theaters

    Valle Drive-In, Newton, Iowa: Surrounded by corn, Valle (left) feels like the movie-theater version of Field of Dreams. Vintage ads play during intermission. (641) 792-3558; valledrive-in.com

    Cherry Bowl Drive-In Theatre, Honor, Michigan: Caramel corn and a strict no-smooching policy give this drive-in near Traverse City a wholesome vibe. For a laugh, call the hotline to hear the owner shout the upcoming features. (231) 325-3413; cherrybowldrivein.com

    Midway Drive-In and Diner, Sterling, Illinois: The parking lot at Illinois' longest continually operating drive-in (open since 1950) fits 500, but the first three rows are reserved for small cars. (847) 647-3124; themidwaydrivein.net

    Boulevard Drive-In, Kansas City, Kansas: A fabulous marquee and Labor Day car show add retro flair, and the digital sound system (first in the world for a drive-in) is fantastic. (913) 262-2414; boulevarddrivein.com

  • Favorite Midwest diners

    Mickey's Dining Car, Saint Paul: It might not be the cleanest place ever, but you can't beat the time-capsule spirit (or the bean soup) at this classic diner (left). (651) 222-5633; mickeysdiningcar.com

    Dawson And Stevens Classic 50's Diner, Grayling, Michigan: Coke memorabilia fills the old pharmacy cabinets at this former drugstore. Try the American Pie, a grilled-cheese with apple pie filling. (989) 348-2111; bottlecapmuseum.com

    Nu Grille, Fort Scott, Kansas: Locals talk up the hamburgers with grilled onions, but don't miss the chocolate shakes at this 1946 small-town diner. (620) 223-9949

    Cindy's Diner, Fort Wayne, Indiana: Expect to rub elbows with other diners (all 15 of 'em) at this tiny, cash-only lunch counter, where regulars order an egg scramble called The Garbage. (260) 422-1957

  • Favorite Midwest soda fountains

    Crown Candy Kitchen, St. Louis (Left): Try the 14 percent butterfat ice cream in a butterscotch malt or pecan-topped Crown Sundae. See reviews and ratings. (314) 621-9650; crowncandykitchen.net

    Bauder Pharmacy, Des Moines: A secret even to many locals, this nothin'-fancy drugstore and soda fountain serves luscious homemade ice cream. See reviews and ratings. (515) 255-1124; bauderpharmacy.com

    Wilson's Restaurant and Ice Cream Parlor, Ephraim, Wisconsin: Many booths at this Door County standby have a jukebox, and cones come with a jelly bean at the bottom to stop the drips. Open seasonally. See reviews and ratings. (920) 854-2041; wilsonsicecream.com

    Lagomarcino's Confectionery, Moline, Illinois: Sundaes come with a little pitcher of hot fudge at this beautiful, turn-of-the-century soda shop, complete with marble tabletops and Tiffany-style lamps. See reviews and ratings. (309) 764-1814; lagomarcinos.com

  • Favorite Midwest drive-in restaurants

    Rudy's Drive-In, La Crosse, Wisconsin (Left): Roller-skating carhops don poodle skirts for classic-car nights, and the menu includes a vegetarian walnut burger. Open seasonally. (608) 782-2200; rudysdrivein.com

    Lakeview Drive Inn, Winona, Minnesota: Open since 1938, Lakeview hosts weekly cruise nights and serves sweet-potato fries and a surprising variety of burgers (beef, elk or buffalo). Open seasonally. (507) 454-3723; lakeviewdriveinn.com

    Original Root Beer Stand, Culver, Indiana: Remember that little tray that attaches to your window? They've got 'em. Ask for a frosty mug to savor the root beer. Open seasonally. (574) 842-2122; Original Root Beer Stand on Facebook

    Sumburger Drive-in, Chillicothe, Ohio: Eat in your car or order from tableside phones indoors. The signature burger is big, halved and topped with a tangy sauce. (740) 772-1055; sumburger.com

  • Midwest retro destinations

    Woodward Dream Cruise, Detroit: The World's Largest Car Event (left) stretches over 16 miles and attracts more than 1.5 million people and 40,000 vehicles. Pack a lawn chair and water. August 16, 2014.  woodwarddreamcruise.com

    Surf Ballroom, Clear Lake, Iowa: Buddy Holly, Ritchie Valens and the Big Bopper played their last show here. A small museum recalls "the day the music died," and the Winter Dance Party sells out. (641) 357-6151; surfballroom.com

    Back To The 50's Weekend, Saint Paul: Owners love to brag on their "babies" at this huge car show (June 20-22, 2014) with fun extras such as cover bands. msra.com

    Boondocks, Deadwood, South Dakota: Families dig the vintage carnival rides, authentic diner and classic cars at this retro fun park. (605) 578-1186; fiftiesfun.com

    (A version of this story appeared in Midwest Living® March/April 2011.)

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