Chester’s Drive-In

Chester’s Drive-In in Plymouth, Wisconsin, is a beloved retro-style eatery known for classic American comfort food and an authentic drive-in experience. With a stellar 4.7 average rating from over 1,300 reviews, this local favorite offers nostalgic curbside service and a menu filled with burgers, fries, shakes, and more. Its welcoming atmosphere and efficient service make it a must-visit spot for families, travelers, and anyone craving a taste of Americana.

Local Tips

• Arrive early during peak lunch and dinner hours to avoid longer wait times.
• Try their house-made root beer float—a customer favorite.
• Classic car enthusiasts often gather here in the evenings for an impromptu show.
• Most seating is in your vehicle, but limited picnic tables are available.

Cost Range

• Burgers and sandwiches: $4–$8
• Fries and sides: $2–$4
• Shakes and floats: $3–$5
• Family meal combos: $15–$25

Parking Advice

• Plenty of designated drive-in parking spots are available for curbside service.
• During busy summer weekends, overflow parking may be needed on nearby streets.
• Staff will come to your car to take your order and deliver your food.

Frequently Asked Questions

• What are Chester’s Drive-In’s most popular menu items? The cheeseburgers, homemade root beer, and classic milkshakes are top favorites among regulars.
• Is Chester’s Drive-In open year-round? No, Chester’s Drive-In is typically open seasonally from spring through fall.
• Do they accept credit cards? Yes, both cash and major credit cards are accepted for payment.
• Are there vegetarian or gluten-free options? The menu primarily features classic diner fare, but some vegetarian options like grilled cheese and fries are available. Gluten-free choices may be limited.
• Is seating available outside of your vehicle? Limited outdoor picnic tables are available, but most guests enjoy their meals in their cars.
• Can I place an order ahead of time? Chester’s Drive-In mainly operates on a first-come, first-served basis at your car, with no standard call-ahead ordering.
• Is Chester’s Drive-In family-friendly? Absolutely! It’s a popular spot for families, with kid-friendly menu options and a fun atmosphere.
• Are pets allowed? Well-behaved pets are welcome in your vehicle, but are not permitted at picnic tables or inside service areas.
• Is there a kid’s menu? Yes, there are smaller portions and simple meals available for children.
• Do they host or participate in special events? Occasionally, Chester’s Drive-In participates in local car shows and community events—check their social media for updates.
• Is there a wait during peak times? Yes, evenings and weekends can be busy, so arriving early or visiting on weekdays can help you avoid longer waits.

Chester’s Drive-In

Sheboygan
Wisconsin

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Chester’s Drive-In
Chester’s Drive-In, 1504 Eastern Ave, Plymouth, WI 53073
(920) 892-7722
Rating: 4.7 average from 1318 reviews.

Read Reviews
Chester’s Drive-In website