Chester's Drive-In

10/06/2026

Please note: Posts on this page are for the Plymouth Location, 1504 Eastern Ave only! If you would like information on the Sheboygan location, please follow Chester’s Waterfront !

10/02/2026

10/01/2026

🍁Happy fall everyone!🍁

The wait is officially over—Our Caramel Apple Sundaes are officially back on the menu starting today.🍏✨
Nothing says fall like crisp apples and warm, gooey caramel layered over creamy ice cream. Come get yours exactly the way you love it:
🥜 With peanuts
🚫 Without peanuts
Hurry in and kick off the cozy season with a spoonful of fall! 🍦🍂

09/24/2026

Say hello to Isabelle, who is doing her Youth Apprenticeship here this fall! 👋✨ We are so glad she is here and learning all the different positions here! 😊🎓🎉

Meet Isabelle, a student at Elkhart Lake-Glenbeulah School District and Youth Apprentice at Chester's Drive-In! 🍦

Isabelle shared:

“I enjoy working at Chester's Drive-In because I get to work with different people and be part of a fun environment. I have learned how to communicate with customers, work as part of a team, and handle different responsibilities. The YA program has given me the opportunity to gain real work experience while still in high school and learn skills that I can use in the future. I am thankful for the experience because it has helped me become more confident and responsible in the workplace.”

Isabelle, thriving in a fast-paced team setting takes real adaptability, and it's wonderful to see how much your confidence and self-reliance have grown. You’ve turned your high school apprenticeship into a powerful personal launchpad for whatever path you choose next!

👉 If you're interested in learning more about Youth Apprenticeship opportunities for Elkhart Lake-Glenbeulah students, connect with NEWYA School-Based Coach Angela Heinz at [email protected] today!

09/21/2026

Back for a limited time, our mushroom and swiss! Try it with a steak! Also, don't forget our pickle fry special is ending soon so stop by before it's gone!

09/14/2026

We have a new, limited time special! Come try the Chipotle burger, made with bacon, gouda cheese, and Chipotle mayo! 🌶😋

Also don't forget to stop in today, September 14th, from 11-2 and support Emma and MHA, in honor of Aaron's memory! 💜🩵

09/09/2026

🎃🍂PUMPKIN CHEESECAKE FLURRY!!!🍂🎃

Fall flavors are here! 😍 Try one of our delicious pumpkin treats:
🥤 Pumpkin Shake or Malt
🍰 Pumpkin Cheesecake Flurry

Come get your pumpkin fix while you can! 🎃🤎🧡

09/07/2026

🇺🇸❤️ Happy Labor Day! ❤️🇺🇸

We’re OPEN ALL DAY TODAY! 🎉🍔🍦

Make the most of your long weekend and stop by for all your Chester’s favorites! 😋🧡 We’ll be here all day serving up good food, sweet treats, and Labor Day smiles! 🇺🇸

Send a message to learn more

09/04/2026

Stop in this holiday weekend and get a cotton candy flurry and pickle fries for a limited time! 🥒🍬