Worth the Drive: Drive-In Restaurants 

Posted on July 9, 2020 by Alisa Lewis

These drive-in restaurants just beyond the Fox Cities offer a dose of nostalgia for hungry roadtrippers. You’ll be sure to find a community-oriented atmosphere in any of these popular spots. Many of these drive-ins have been staples of their towns for decades, and are beloved by locals and visitors alike. 

Milty Wilty, Wautoma 

Milty Wilty is a well known drive-in located in the quaint city of Wautoma. Best known for their custard and famous malts, the drive-in has become a staple in the Wautoma community and beyond. Owner Cynthia Sommer shares that Milty Wilty has a loyal following, with people driving long distances to experience the vintage restaurant. The restaurant even boasts a Facebook fan page, composed of over 900 enthusiastic members, who post pictures of their visits and share memories of their time spent there. And lots of memories there are. Milty Wilty was first started in 1947, by Sommer’s father, Milton, as a custard stand. Since then, the restaurant has expanded to offer a dining room, outdoor seating and a mini-golf course. The drive-in offers pizza, burgers, fish and chicken dinners, but the most popular menu items are their famous frozen custard, sundaes and malts. The drive-in has increased safety practices due to COVID-19 and offers window service, as well as new outdoor seating options. 

The Well, Winneconne 

The Well in Winneconne is another example of a drive-in that is a long-standing community staple. This adorable window service restaurant has been open since 1954 and is dripping with ‘50s and ‘60s nostalgia from the moment you walk up and order. Part owner and manager Jeff Weber, who has owned and operated the restaurant with his wife Judy since 2001, explains that the restaurant is community-based to the core. “We’ve seen third-generation customers come to the restaurant, many mentioning how they used to come as a child with their grandparents and made sure to stop by even when they have moved out of the area,” he says. Along with the family aspect of the drive-in, Weber notes that the drive-in’s cult following includes locals as well as those who have vacation homes in the area. “There are always so many stories to listen to about people who have been customers for years,” he says. Despite the pandemic, this mom-and-pop walk up eatery has been able to operate fairly normally, as the window service provides almost no contact. However, the picnic tables for eating on the premises are currently closed. Along with increased sanitizing procedures and online ordering, business has been fairly average during the pandemic, Weber explains. The Well offers a quality menu with popular items including ice cream, burgers and roast chicken. One of their biggest draws is their Friday fish fry, which Weber says is fantastic and a great-seller. 

Timberlea Drive In, Abrams 

With a scenic location on the ninth hole of the Pine Acres Golf Course along the Pensaukee River, Timberlea Drive In is a must visit restaurant. Coreen and Luke Lemorande have owned and operated Timberlea for the past 25 summers, but the restaurant has stood since the late 1950s. The drive-in sells the most classic ice cream cones, in either cake or waffle cones. Coreen explains that their pistachio ice cream is a customer favorite. “The Timberlea is unique because of the high quality of our custard that is sourced locally,” she says. Timberlea’s family-oriented atmosphere is created by generations of families for whom a stop at the drive-in is tradition. “They love to tell us about stopping on the way to or from their cottage every weekend or coming in after every baseball game,” Coreen says. “They watch for the [ice cream] flavors to change and make a special stop to enjoy it.” The drive-in is focusing on keeping their employees and customers safe by following health department guidelines, maintaining social distancing standards, as well as enforcing disinfectant regimens.  

Rudy’s Drive-In, Sparta

A drive-in dating back to 1933, Rudy’s Drive-In is a vintage tradition in La Crosse and Sparta. The drive-in is best known for its old school charm, complete with roller-skating carhops. The restaurant has been owned by the Rudy family for generations, most recently being owned by Gary Rudy. Rudy says the restaurant is unique in the fact that not only has it been family owned for 87 years, but the restaurant has grown in versatility, offering “many choices of where to eat, inside, outside at picnic tables, in your car, or as takeout.” Not only is the restaurant strong in location, they offer a range of food options to appeal to everyone. Rudy explains that their most popular items include chili dogs and Flavor Burst cones with “several ice cream flavors mixed together.” He says that his restaurant attempts to cater to many, offering gluten-free and vegetarian options. The drive-in also offers freshly brewed root beer, originating from the restaurant’s roots as a root beer stand nearly 90 years ago. During the pandemic, Rudy has continued to serve the community through a take-out format, but will be opening the premises shortly to those who want to eat near the restaurant.   

Shepard’s Drive-In, Berlin

Shepard’s Drive-In, a traditional drive-in located in Berlin, has been family owned since its beginning in the 1960s. Owner Ron Ross explains that he and his wife Arielle have a collective “39 seasons of experience” working at the restaurant and plans to “continue the ‘Berlin area tradition’ for a long time to come.” Shepard’s offers an extensive menu to complement the family-oriented atmosphere. “We have so many options that everyone can find something that they love, be it a unique ice cream treat or combo, or any of our delicious food offerings,” Ross says. “We pride ourselves on the speed of service, menu options, customer service, and the general small-town good feeling [customers] get by supporting our business.” Ross began his journey as an employee himself and enjoys witnessing the legacy a drive-in can create. “We have a great loyal customer base. Regulars that I’ve seen over my 24 years at the drive-in are now coming in with their kids or grand kids. It’s something that you pass on from generation to generation,” he says. One the food front, Shepard’s offers many popular choices, from their signature Shepard’s deluxe burger, pizza burger and their number one selling side, cheese curds. Ross suggests coupling any entree with one of the homemade side offerings such as the famous potato salad or coleslaw. Ross says the efforts of his employees have paid off as they work through changes due to COVID-19. “We were able to adapt to COVID-19 because we are known for great take out and customers seem to be responding very well to our efforts of delivering the food to their vehicles which keeps our employees safe as well as our customers,” he says. Currently, the restaurant offers take-out and outdoor seating, altering their approach as needed. 


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Food & Dining, Worth the Drive

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