Chester's, one of our favorite Wisconsin Drive-Ins.

17+ Wisconsin Drive-Ins To Try Across the State

Wisconsin Drive-Ins: Dick's in KaukaunaWisconsin Drive-Ins mean some delicious treats on a tray or at a picnic table

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. Some will be closing as we go through September, some will stay open well into autumn and beyond. Here are 17 (okay now 18 and perhaps more coming soon) Wisconsin Drive-Ins across the state to try!



 

Chester’s Drive-In, Plymouth

1504 Eastern Avenue (County C, old Highway 23)
Plymouth, WI 53073
(920) 892-7722
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Chester's, one of our favorite Wisconsin Drive-Ins.

Chester’s cheeseburger, fried mushrooms, and a chocolate malt. It immediately became one of our favorites.

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) and 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. This is the “old” Highway 23, with Highway 57 less than a mile to the east, the current Highway 23 expressway less than a mile to the north, and Highway 67 less than a mile to the west in downtown.

Chester's Drive-In, Plymouth

Wisconsin Drive-Ins: The Drive-In, GrantsburgThe Drive-In Restaurant, Grantsburg

133 Highway 70 (at Hwys 48 & 87)
Grantsburg, WI 54840
(715) 463-2056
Website

Complete with 45rpm records and memorabilia adorning the walls, the Drive-In in Grantsburg opened in 1956 and continues its heritage with signs like its root beer float along Highway 70. Their burgers and grilled sandwiches, crinkle-cut fries and onion rings, fried cheese curds, milkshakes, and root beer are among the tops in NW Wisconsin; it’s also a popular draw for Twin Cities travelers and car culture enthusiasts. Dine-in service is available all year, with the outdoor drive-in bays open seasonally. Discover Wisconsin featured The Drive-In on an episode exploring drive-ins in the state. And being right near the state line, it’s one of the more popular Wisconsin drive-ins for Minnesotans to come try. You’ll find The Drive-In in Grantsburg along Highway 70 in Burnett County, within sight of where Highways 48 and 87 end (it’s as if all roads in the area lead to it!)

Hager Heights Drive-In, Hager Heights

7866 170th Avenue (U.S. 63 & Highway 35)
Hager City, WI 54014
(715) 792-2118
Facebook page

Wisconsin Drive-Ins: Hager Heights

Famous particularly for broasted chicken, Hager Heights draws in people from nearby Red Wing, MN, Ellsworth, Twin Cities area travelers, and people heading up and down the Great River Road. This drive-in is perched right where U.S. 63 and Highway 35 meet, about a mile east of the Mississippi River in Wisconsin’s beautiful Driftless Area. Hager Heights Drive-In is open from early April to the end of September (give or take) and has a series of bays for cars, bikes, and trucks to park under while being served their signature items. Along with the broasted chicken (a large fiberglass chicken out front should make the entrance easy to spot), Hager Heights does up the quintessential burgers, fries, rings, shakes, and more for hungry travelers.

Milty Wilty Drive-In, Wautoma

W7411 Highway 73
Wautoma, WI 54982
(920) 787-2300
Website

Milty Wilty, one of our favorite Wisconsin drive-ins

Opened on June 11, 1947, the Milty Wilty serves up classic fare indoors and out during the warm weather months (generally May-September) along Highways 21 & 73 approaching Wautoma. Still a family business and now in its 4th generation, the milkshake machines hum, cones fill with ice cream and custard, and burgers sizzle. The Milty Wilty also introduced the “pizza pie” to the area when it first opened, and the pizza burger is one of their most popular items. Dine in, or pull to a space and get served by a car hop; you can even enjoy some mini-golf on their adjacent course. They offer “Cruise Nights” on Thursdays if you want to admire some true classic cars and street rods, a popular feature at many of the classic Wisconsin drive-ins.

Mullin’s Short Stop, Columbus

641 N. Ludington Street (Highway 73/historic US 151)
Columbus, WI 53925
(920) 623-2080
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Wisconsin Drive-Ins: Mullins Short Stop in Columbus along Highway 73

Mullins Short Stop along Highway 73 (photo credit: TripAdvisor user DuaneB.)

Mullin’s Short Stop opened as Brown’s Drive-In during the 1950s, when this stretch was not only Highway 73 but also part of U.S. 151, the main road from SW to NE Wisconsin. A bypass around Columbus completed in 1976 cut traffic a bit, but the Drive-In held on thanks to loyal customers from in and around the town. Brown’s became Mullin’s around that time and continues to delight burgers, fries, and shakes lovers to this day. Mullin’s is open from mid-May through Labor Day.




Ardy & Ed’s Drive-In, Oshkosh

2413 S. Main Street (U.S. 45)
Oshkosh, WI 54902
(920) 231-5455
Website

Ardy & Ed's Drive-In, Oshkosh

Roller skating car hops and food on a tray with a view of Lake Winnebago and 50s & 60s tunes playing outside. That, along with delicious classic American food, has been drawing people to here since 1948 – some of whom arrive by boat. Located right along U.S. 45 on the south side of Oshkosh, Ardy & Ed’s began as an A&W stand and went independent in 1972 with its new name. Being one of the oldest Wisconsin drive-ins, Ardy & Ed’s celebrated its 70th anniversary in 2018. They have a jingle too; you can hear that and see more here:

Leon's Frozen Custard, Milwaukee

Wisconsin Drive-Ins: Leon's Frozen Custard along Historic 27th Street in MilwaukeeLeon’s Frozen Custard, Milwaukee

3131 S. 27th Street (Highway 241, Historic U.S. 41)
Milwaukee, WI 53215
(414) 383-1784
Website

Considered by many to be the quintessential American drive-in, and perhaps part of the inspiration for Mel’s Drive-In in American Graffiti and Arnold’s in Happy Days, Leon’s has been in operation since 1942. An early 1950s remodel adding the fluorescent lights and neon signs gave Leon’s its current look. To this day, Leon’s serves some of the highest-rated frozen custard in the country along great malts, shakes, floats, and sundaes. They don’t have car hops and they don’t serve burgers (although Mazo’s across the street dates back to 1934 and has awesome ones), but Leon’s does serve tasty hot dogs, chili dogs, and a Spanish hamburger, which like a spicy sloppy joe. On a warm summer night, expect quite a crowd in line and in the parking lot along this 27th Street location. It’s currently Wisconsin Highway 241, but was once U.S. 41 and the main road in from Chicago – one of the reasons Leon’s drew so much traffic and became so widely known.

Kitt’s Frozen Custard & Burgers, Milwaukee

7000 W. Capitol Drive (Highway 190)
Milwaukee, WI 53216
(414) 461-1400
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Kitt's Frozen Custard along Highway 190/Capitol Drive

Kitt’s opened in 1950 along Milwaukee’s Capitol Drive, the main east-west thoroughfare across the city’s north side. Long known for jumbo burgers and frozen custard, Kitt’s has held on through plenty of changes and continues to serve sundaes, shakes, burgers, onion rings, and fries. The classic neon sign and 50s feel continues to charm. Kitt’s is open from 11am – Midnight most days, and they’re open year ’round. You order at the walk-up counter, there are no car hops.

Wayne’s Drive-In, Cedarburg

1331 Covered Bridge Road (Highways 60 & 181)
Cedarburg, WI
(262) 375-9999
Website

Wayne's Drive-In, Cedarburg

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.

Wisconsin Drive-Ins: Classic Car Show at Wayne's in Cedarburg

Wisconsin Drive-Ins: classic car show at Wayne's in Cedarburg

The Kiltie, Oconomowoc

N48W36154 Wisconsin Avenue (Historic U.S. 16)
Oconomowoc, WI 53066
(262) 567-2648
Facebook page

The Kiltie, one of Wisconsin's best drive-ins

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.
The Kiltie original sign

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.

Wisconsin Drive-Ins, The Kiltie Burger (with onion)

A Kiltie Burger, clearly with onions, in Oconomowoc along Highway 16.

The Spot, Kenosha

2117 75th Street
Kenosha, WI 53143
(262) 654-9294
Website

Opening on July 4, 1945, The Spot is a true classic. It’s one of the oldest surviving drive-ins in the country, and certainly one of the oldest of the Wisconsin drive-ins. They still make their own homemade root beer and have been hitting home runs with burgers, fries, onion rings, and shakes since World War II (in fact, one of their big challenges was getting supplies, since the war was still going on.) Their menu is much larger now, including mini-tacos, perch, chicken wings, and cheesecake, but the traditions hold true with car hops and the iconic neon sign on the corner.

The Spot was once also the intersection of Highways 50 & what used to be Highway 174, which came in from the south for Chicago travelers, making it once a primary intersection in Kenosha for travelers looking to head downtown. Today, it’s a little quieter traffic-wise but The Spot still serves as a big draw for any fans of classic drive-ins and fantastic burgers.

Andy’s Drive-In, Kenosha

2929 Roosevelt Avenue (Highway 50)
Kenosha, WI 53143
(262) 658-2067
Website

Wisconsin Drive-Ins: Andy's in Kenosha

Andy’s in Kenosha. The “A” on the top is reminiscent of “Arnold’s”, the fictional drive-in from the TV show “Happy Days.”

Andy’s is a classic drive-in that dates back far into Kenosha’s history, which has always been big on car culture, competing with The Spot nearby. Their Cruise Nights are still immensely popular. Along with serving traditional burgers, fries, shakes, and other drive-in fare, Andy’s dishes up well-loved breakfasts too, and opens early: 6am Monday-Friday and 7am on weekends. It’s right along Roosevelt Road/Highway 50 in Kenosha.

Gus’ Drive-In, East Troy

3131 Main Street, County ES/Historic Highway 15
East Troy, WI 53120
(262) 642-2929
Website

Wisconsin Drive-Ins: Burger and rings at Gus' in East Troy

Located along Historic Highway 15 – the main road from Beloit to Milwaukee before I-43 came along – Gus’ Drive-In in East Troy dates back to 2002 but offers the full 1950s vibe. Home of the “Heavy Chevy” Burger, Gus’s is close to Alpine Valley, the East Troy Railroad, and is only minutes from I-43 or Highways 20 and 120. Gus’ features frozen custard – with flavors of the day on their Facebook page – rather than ice cream with a different flavor-of-the-day everyday. They also specialize in Greek gyros and Italian meatballs on top of the classic, where they’re often in the running for “best burger.” Gus’ also features regular Cruisin’ Nights on Saturdays. This is definitely a place to bring your street rod and immerse yourself in that time! In season, Gus’ is open every day from 11am-8pm.

Wisconsin Drive-Ins: Gus' in East Troy




Wisconsin Drive-Ins: Rudy's in La Crosse along Highway 16Rudy’s Drive-In, La Crosse

1004 La Crosse Street (Highway 16)
La Crosse, WI 54601
(608) 782-2200
Website

Rudy’s Drive-In, Sparta

514 S. Water Street (Highways 16 & 21)
Sparta, WI 54656
(608) 269-2011
Website

Rudy’s Drive-In opened in La Crosse in 1966, but origins of Rudy go back to an A&W Root Beer stand in Chippewa Falls in 1933. The La Crosse location, and the newer Sparta one, are still owned by the Rudy family. We’re consolidating these two locations into one entry!

Rudy’s features a bright roof to shelter at least part of your vehicle and car hops bringing you the tray of tasty treats. They’re one of the few drive-ins offering gluten-free buns and even some healthy choices like a Turkey Burger and their Historic Trempealeau Hotel Walnut Burger, which we’ve had at the Trempealeau Hotel. It’s a seasoned walnut & cheese patty with lettuce, tomato, pickle and honey mustard on a whole wheat kaiser bun. Not your traditional drive-in food, but it’s certainly a good option for many! On select Cruisin’ Nights, showing up in a classic car or on a classic bike gets you a free root beer float.

Charlie’s Drive-In, Hortonville

806 W. Main Street (Highway 15)
Hortonville, WI 54944
(920) 779-6753
Website
Facebook page

Wisconsin Drive-Ins: Charlie's in Hortonville

A family business since 1965, Charlie’s Drive-In keeps it “homespun,” as they like to say. Tuesday nights are for classic cars (a “Collector” license plate gets you a free mug of root beer), and they have a tributes to Elvis every year on the anniversary week of his passing. Plenty of tunes and a classic menu with a busy fryer keeps things fun and happy at Charlie’s. They are generally open from mid-March through the end of September. You’ll find Charlie’s along Highway 15 (formerly U.S. 45) in Hortonville, about 15 minutes northwest of Appleton.

Dick’s Drive-In, Kaukauna

1718 Crooks Avenue (Highway 55)
Kaukauna, WI 54130
(920) 766-3511
Facebook page

Wisconsin Drive-Ins: Dick's in Kaukauna

Home of the “Maxi Burger,” Dick’s Drive-In opened in 1955 along Highway 55 and is open from March 1st – November 30th, which is pretty long season given the weather rarely cooperates for several of those months. However, they generally don’t have car hops – you go inside the little area in front to place your order. You’re welcome to enjoy it in your car in the lot, at a picnic table in the back, or of course to bring it home or eat it on the run. Broiled burgers (the neon is there to remind you of their broiling process), a variety of sandwiches, sides, shakes, slushies, floats, and flurries are all part of their popular menu. To help with flashing back, the interior of Dick’s has stayed essentially the same since the 1950s, keeping it one of the most original of our Wisconsin drive-ins!

The Albatross Drive-In, Washington Island

777 Main Road
Washington Island, WI 54246
(920) 847-2203
Website

Wisconsin Drive-Ins: Albatross on Washington Island

This is the only one of our Wisconsin drive-ins that requires a boat ride first. Once you reach the end of Highway 42 at the tip of the Door County Peninsula, the Washington Island Ferry will take you to County W on Washington Island, where a short ride lets you adjust to “island time” and prep your tummy for a tasty Alby Burger, fries, rings, cheese curds, or ice cream. They make it a point at The Albatross to note that they’re “not fast…but we’re good!” And they definitely are. It’s been around since the 1970s, although the current building only dates back to 2002, a rebuild after a fire. The Albatross generally doesn’t serve you “car hop” style, but you’re welcome to eat in your car in the lot, on the bike you rented on the island, or at the tables outside – some of which are under cover. It’s definitely a nice, relaxed setting where the food is fantastic and nobody is in a hurry… hopefully.

Albatross Drive-In sign for Illinois visitors.

The Albatross sets some ground rules as you prepare to order.

What’s your favorite of the Wisconsin drive-ins?

And there you go: 18 of our favorite drive-ins in Wisconsin as we road trip around the state. Did we miss one of your favorites? We know that’s quite possible, and that’s cool… because the more great drive-ins we can all know about, the better! It’s why we added Chester’s in Plymouth to our original 17 (totally an oversight on our part, we fully admit!) Let us know in the Comments below, and we’ll be happy to pay your favorite place a State Trunk Tour visit!




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7 Responses to "17+ Wisconsin Drive-Ins To Try Across the State"

  1. Jeff Thomas
    Jeff Thomas 1 month ago .Reply

    You missed BIG STARE in Kenosha Wi.

  2. Jim
    Jim 1 month ago .Reply

    Rumble seats in spring green.

    • Eric Paulsen
      Eric Paulsen 1 month ago .Reply

      AH, along U.S. 14. Yes! Haven’t stopped in and tried it but we did get a picture. We’ll add it to the next one, or if we get there soon, add it to this article. Thanks, Jim!

  3. Penny Gneiser
    Penny Gneiser 1 month ago .Reply

    John’s Drive In – Waukesha, WI. Open all year long. They make their own Root Beer.

  4. Penny Gneiser
    Penny Gneiser 1 month ago .Reply

    John’s Drive In – Waukesha WI. Open all year long. They make their own Root Beer.

  5. Ilsa Lermenn
    Ilsa Lermenn 3 weeks ago .Reply

    Hamburger Haus Dundee , Mickey Lu’s BBQ Marnette and Chesters Plymouth

    • Eric Paulsen
      Eric Paulsen 3 weeks ago .Reply

      Hi Ilsa, we’ll have to explore Hamburger Haus and see if it qualifies as a “drive-in” like the others, and Mickey-Lu is one of our favorites but it’s not technically a drive-in. But Chester’s in Plymouth – YESSSS! That was a miss on the first try, so we’ve added it and updated the article. Thank you! 🙂

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