If you love Wisconsin road trips, you probably love Wisconsin drive-ins. The American classic place to pull in, order tasty fare - often from a car hop, sometimes on skates - and eat in your car off a tray hanging on your window or at a picnic table with tasty burgers, fries, onion rings, ice cream or custard, malts, shakes, and whatnot. Thousands upon thousands of drive-ins populated the country in their heyday, and Wisconsin had many. A&W Root Beer stands were popular and still love on in various towns across the country, while the Sonic chain has brought the concept back in many other locales.
But here in Wisconsin, we love the independent drive-ins that survive, many of which are family-owned businesses going back generations. While the warm weather still lasts, here are 17 Wisconsin Drive-Ins across the state to try. Included are the classic Leon's and Kitt's in Milwaukee, The Kiltie (an Oconomowoc classic), Wayne's Drive-In in Cedarburg, and, well, a bunch of others from NW Wisconsin to Washington Island and from La Crosse to Kenosha!
Here are three of them to start with:
Chester’s Drive-In, Plymouth
1504 Eastern Avenue (County C, old Highway 23)
Plymouth, WI 53073
Chester’s Drive-In, an addition to our original article, deserves to be among the top! A family business since the 1970s, Chester’s Drive-In has friendly car hops and a nice variety on their menu, which is tucked into the top of the metal roof that cars park (partially) under. They’re known for great cheeseburgers - the bakery buns hold all the toppings in nicely - as well as their root beer. On a visit, we went for the malt and it was fantastic. They offer fries, rings, and a variety of sides – including fried mushrooms, which just seemed to hit the spot that day. Chester’s is open April through October. You’ll find it right along County C/Eastern Avenue on the east side of Plymouth just west of Highway 57, about an hour north of Milwaukee.
Wayne’s wasn’t around in the 1950s & 60s, but it sure seems like it. The building is 12-sided – technically a dodecagon – and dates back to the early 70s. The building previously served as a snowmobile shop, a storage facility, and a furniture refinishing shop before it became one of our favorite Wisconsin drive-ins, becoming Wayne’s Drive-In in 1998. The classic burgers and shakes, ice cream, skating car hops, and overall vibe draw people from all over SE Wisconsin. Corvette Cruise Nights run select Wednesdays, Classic Cruise Nights run select Thursdays. Wayne’s is open every day from 11am to 9pm during the season, which generally runs from early April through early November.
The Kiltie, Oconomowoc
N48W36154 Wisconsin Avenue (Historic U.S. 16)
Oconomowoc, WI 53066
A classic since 1948 with post-war architecture, the smiling Scotsman logo, and car hops in plaid Scottish skirts, The Kiltie keeps bringing customers – and employees – back decade after decade. Their classic burgers, onion rings, sundaes, malts and other essentials are second to none, in part because everything seems to taste better when served on an aluminum tray. You want custard? Your choices are simple: chocolate, vanilla, or a twist of the two; no flavors of the day here. The car hops like to have fun, too: some refresh people with water guns on hot days, and when business is slow frisbees may fly around the parking lot.
Located along old U.S. 16 on the east end of Oconomowoc, The Kiltie also nestles up against the current Highway 16 freeway, easily accessible via the County P exit a little bit east of Highway 67. The neon signs that mark this classic are visible from either road and beckon you to the numerous pull-in spots for your car so the hops can get your order. The Kiltie is open from April through October.