My childhood “drive-in” was a place in Shorewood called Pig ’N Whistle. It was mainly a sit-down joint serving casual, conventional American food. It also had a walk-up window in the rear that was all carryout – burgers and a fountain menu.
It was known, affectionately, as the “back of the Pig.” We’d roll into the parking lot (one of my brothers driving my mom’s car) on a sticky summer night for what to me was the fast food burger to end all. The Pig was an institution, but it was no drive-in.
It’s time to pick your Milwaukee favorites for the year!
At the true drive-in of yesteryear, you stayed in your car. A server (maybe on roller skates) would take your order at your car window, then deliver the food to you, attaching a serving tray to your window.
These days, the classic 1950s nostalgia drive-in is often more loosely defined, trading the carhop service for diner-like inside seating. But the spirit – the carefree-summer fun – of the originals is all there.
These seven Wisconsin drive-ins, a mix of true oldies and more modern counterparts, serve up a classic (or classic-inspired) experience, building memories one burger at a time.
1. The Kiltie
N48 W36154 E. WISCONSIN AVE., OCONOMOWOC
You haven’t really done the time-warp unless you’ve pulled in under the canopy of this 1940s-era institution in Lake Country. (The giant, beacon-like neon sign is an appetite stimulant.) Young carhop servers clad in short kilts keep the orders moving.
Though the burger here isn’t my favorite, they make excellent onion rings (thick, sweet slices coated in crisp breading), and the frozen custard creations are just great. I’m a sucker for a vanilla-chocolate twist cone, but if I’m feeling self-indulgent, it’s the Fudge Royal sundae. $4-$20. Cash only. Open April-Sept. Daily 10 a.m.-9 p.m.
2. Wayne’s
1331 COVERED BRIDGE RD., CEDARBURG
In 1998, Harley-Davidson dealer Wayne Houpt realized a long-held dream to open a diner/drive-in, repurposing a 1960s octagon-shaped building. With a sign that rises out of the cupola like an antenna, the drive-in looks like it came from the set of American Graffiti. Houpt, who passed away in 2021, was a man of simple culinary taste, preferring a burger and fries to a “five-star restaurant,” says Todd Berlin, who operates Wayne’s.
This place – with inside and patio seating, plus a convenient walk-up window – keeps it simple. I’m more drawn to the atmosphere than the food, though I’d never turn down a thick, rich chocolate shake. $4-$16. Open April-Nov. Tues-Sun 11 a.m.-8 p.m.
3. Big Star
1500 WASHINGTON RD., KENOSHA
A Big Star fan Facebook group makes the bold claim that this is “quite possibly the best drive-in in the world.” Who’s to say it’s not, right? Honestly, they had me at the big red sign, a bubble-lighted arrow capped by a star that guides you to fast food ecstasy.
Owner Chuck Laferney says he hasn’t changed much since his grandfather opened the paragon in 1954. The double cheeseburger is their signature – two patties, two slices of Velveeta, plus onions, ketchup and mustard on a grilled bun. It’s not old-school perfection, but darn-near close. Cash only. $1-$10. Open March 1-Aug. 31. Daily 11 a.m.-10 p.m.
4. Gus’s
3131 MAIN ST., EAST TROY
Despite a vintage 1960s Muffler Man statue looming in front of the restaurant, Gus’s is young – just 22 years old. Yet it looks like 1955 inside. It’s a sit-down joint with counter service and no carhops, but with the whole kit and caboodle of retro decor.
The menu, with gyros and broasted chicken, is more diner than drive-in, and I can’t say that the burger is worth the trip to East Troy. But the throwback fun of it all is, capped off by a slushie or frozen custard drink called a “screamer.” Order the orange one, close your eyes and take a sip, and you’re back on summer vacay from school, licking that prized Dreamsicle. $3-$16. Tues-Thurs 11 a.m.-8:30 p.m.; Fri-Sat 11 a.m.-9 p.m.
5. Ardy & Ed’s
2413 S. MAIN ST., OSHKOSH
This 77-year-old gives me flashbacks of pilgrimages to A&W stands in my dad’s ’73 Plymouth Satellite station wagon. Across the street is Lake Winnebago, so you know this place is packed in the summer. Our young carhop is a pro, steering us to the ground steak sandwich (one-third pound Black Angus) over the regular hamburger. This souped-up burger is straight-up Americana: juicy, tasting like a flat-top grill that’s seasoned well and often.
The fried perch sandwich is just the way I like it, the breading golden and hot and the fish moist and flaky. The perfect vehicle for tartar sauce. But what thrills me the most is the draft root beer, served in a frosted glass mug. It tastes better than I ever remember root beer tasting, and we manage to keep the mug from slipping off the tray attached to our car window. $4-$19. Open March-Dec. Daily 11 a.m.-8 p.m.
6. Leon’s Frozen Custard
121 W. MURDOCK AVE., OSHKOSH
Another Oshkosh drive-in legend, Leon’s Frozen Custard (no relation to the Milwaukee stand) is just a 10-minute drive from A & E’s and serves the best malts and hot fudge sundaes in the vicinity, no lie. Daily 11 a.m.-9 p.m.
7. The Spot
2117 75TH ST., KENOSHA
It’s been said that in Kenosha, the drive-in locals tend to patronize depends where they live – Big Star if they’re on the north side, and The Spot if they’re on the south. That doesn’t mean one is better than the other. Each has its assets. Open since 1945, The Spot has evolved to meet demand. The original teeny brick structure was torn down, rebuilt and expanded in the ’60s.
The menu grew larger; the hours extended, and it shifted from a seasonal business to year-round. You can even place a food order online. Whatever – it still breathes the same air as Fats Domino. You can’t go wrong with the drive-in’s holy grail – a cheeseburger delivered hot, fresh and delicious by your carhop. The soft bun fuses to the gooey cheese while that beef patty breaks through with its caramelized crust.
The crispy fried green beans with ranch dressing are worth ditching the fries for. And do not resist getting a “whirl” – a root beer float (the soda made in-house) whipped into a shake. $3-$13. Daily 11 a.m.-2 a.m.
