Drive-in Dining

Illustration by Ali Bachmann

A NOSTALGIC ANSWER FOR EATING OUT DURING PANDEMIC TIMES

BY SUSAN HARPT GRIMES

In this age of social distancing, our primary dining “out” experiences have mostly been limited to delivery, curb-side and drive-thru. Thankfully there is another option, one that isn’t limited to summer, but definitely enhanced by longer, warmer days: drive-in restaurants. A sort of communal dining experience is created at drive-ins, but close proximity is unnecessary.

For some, drive-ins may conjure up childhood memories of piling into the back seat of Dad’s car for a late night custard run—or bring nostalgia for gathering with friends on a hot summer night to flirt over burgers and fries. The truth about the success of today’s drive-in may be more about our desire for good food, served simply. The following represent just a few of the great drive-ins in our area.

NITE OWL

830 E. Layton Ave.

414-483-2524 | niteowlmke.com

Since 1948, the Nite Owl Drive-in, owned and operated by the Roepke family, has been turning out some of the best burgers Milwaukee has to offer. Handmade patties of the freshest beef, sets a limit on the number of burgers they can serve in a day, so come early to ensure you get yours. A few other sandwiches, crispy fries and onion rings, along with luxuriously creamy shakes, malts, and ice cream sundaes round out the menu. The Nite Owl diverges from many other drive-ins in that they use ice cream, not custard, for their frozen treats. Place orders at the window and remember to bring cash as the Nite Owl doesn’t take cards. Some limited indoor seating is available. Open seasonally from roughly mid-March to November.

LEON’S FROZEN CUSTARD DRIVE-IN

3131 S. 27th St.

414-383-1784 | www.leonsfrozencustard.us

Leon’s is the gold standard for drive-ins in our area. Owned by the same family since it opened in 1942, generations of Milwaukeeans have flocked to Leon’s for their fantastic chili dogs, incredibly rich custard-based shakes and sundaes, as well as their tasty old-fashioned soda fountain flavors. Order at the outdoor counter and make note that while they used to be cash only, Leon’s does take plastic these days. Happily, Leon’s is open year round, so you can get your drive-in fix anytime.

WAYNE’S

1331 Covered Bridge Road, Cedarburg

262-375-9999 | waynesdrivein.com

For nearly 25 years, Wayne’s has been delighting North Shore diners with their buttery burgers, deep fried tots, and silky smooth shakes. In addition to burgers, a few sandwiches, hot dogs, and an excellent Friday fish fry round out the menu. Traditionally, Wayne’s has Classic Car Nights, Corvette Nights, and other themed events for family fun. Wayne’s uses locally made Cedar Crest ice cream, instead of custard for their frozen refreshments. Plan to order at the indoor counter, or outdoor window when open. For those who don’t care to eat in their car, limited indoor seating and outdoor picnic tables are available. Cash and cards accepted. Open seasonally from April to November.

THE KILTIE

N48W36154 E Wisconsin Ave., Oconomowoc

262-567-2648 | kiltie-drive-in.business.site

Dating back to the 1940’s, The Kiltie offers a very classic drive-in experience as they still maintain car hop service. Simply drive up to an empty spot under the canopy, stay in your car to order, and one of the hardworking servers will bring your food right to your car window. The Kiltie goes beyond burgers and fries with their food offerings, branching out with full chicken, shrimp, and fish dinners, as well as several sandwiches and a long list of fried goodies for sides. Decadent frozen custard malts, shakes, and floats go great with your meal, or go just for dessert alone as the sundaes, and cones are excellent. Also, don’t forget your cash as plastic isn’t accepted at the Kiltie. Open seasonally, typically April thru mid-September.

THE SPOT

2117 75th St., Kenosha

262-654-9294 | spotdrivein.com

Like so many of the drive-ins featured here, The Spot has its origin story begin in the 1940s. Operated by the same family for generations, ownership changed hands in 2019. While so much has stayed the same at this historic establishment, like their phenomenal burgers, outstanding homemade root beer, and dynamite ice cream based treats, it’s some of the new developments that set them apart. The new owners have thoughtfully added vegetarian burgers and wings, as well as adding online ordering for take away orders. On-site, the car hops will still take your orders, and dining is limited to your car, all year-round. Only cash is accepted, but there is an ATM available. Also, they are a legitimate late night dining destination, as they don’t close until 2 a.m.

Susan Harpt-Grimes writes about Milwaukee food and culture for the Shepherd Express.