I love drive ins, but this is the very bottom of my list. I don't mind that they only take cash, and it seems to be busy quite often. My problem is the the three time I have went the order was wrong two out of three times and it is the tasteless, seasoning free food ever! Bland as a cardboard box! Three strikes and I am done! I would rather drive to Oshkosh to Ardy and Ed's, for the real drive in experience read more

Best burgers!!! I crave a good Chester burger!! Nothing compares to it!!! Can't leave without a root beer or a freeze for dessert!!!

I've been eating her my entire life! The food is always amazing. I love the cheese burger the most and the root beer is top tier! The service is always very friendly and speedy, even when busy they keep up with orders. It's such a unique place with the eating outside. I love it so much! read more

Chester's Drive-In - Cheese burger with ketchup, mustard, and pickles - Burgers Near Me - Plymouth, Wisconsin

If I could give this place 6 stars I would. Nestled in the heart of Plymouth Wisconsin, you can drive up and enjoy your food in your car or go to the walk up window and sit and relax at a table in the front. Chesters welcomes you to enjoy amazing root beer and amazing burgers and the friendliest servers. I recommend a rootbeer float, papa burger with bacon and extra butter and mayo with a French fry. The prices are great and the service is fast. I hope they never close. read more

Nice waitress, old school ordering no cards only take cash! Really good fried mushrooms, cheese curds, the burger was really good reminded me of White Castle buns. The shake I ordered def didn't taste like Raspberry. We enjoyed the Lemonaid read more

I love the food at Chester's! I always get the chicken sandwich. I love their root beer!!! Buy some to take home. I enjoy the drive-in atmosphere. It takes you back to the good old days. Make sure you get there at least one or two times a summer. read more

Food: 4/5 Service: 5/5 After visiting this place, I have learned how long they have been running and what they do in the off season. It's amazing that small town places like this still thrive and how amazing the food is. The root beer for me was the real treat, it tasted just like I remembered as a kid and was delicious. Can't wait to come back many more times and try the ice cream. read more

Chester's Drive-In - Papa Burger with Bacon! - Burgers Near Me - Plymouth, Wisconsin

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Excellent food and walk up order window! Chester's is a great place that serves up delicious sandwiches and ice cream in Plymouth Wisconsin. I ordered the pork tenderloin sandwich and the papa burger with everything on it. There's a lot going on at this iconic drive up restaurant and the servers keep it moving for sure. Lots of happy families with kids, couples out for dinner and some old timers too. Seems like everybody loves Chester s food and great service read more

Good food good service and over all a good workplace if I could give this 6 stars, I would .

Good food good service. The only thing that doesn't make sense is you can't pay with a card only cash or check .

Chester's is a must for old-fashioned drive-up fun! This has been a summer tradition for us since our children were small! Now we enjoy bringing our grandkids here. We also enjoy Chester's without our kids & grandkids. Great burgers, fries, root beer & especially their orange & white twist cones! We love Chester's!!! read more

Chester's Drive-In - Enormous and delicious orange & white twist cones!! Our Family Favorite!! - Burgers Near Me - Plymouth, Wisconsin

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For the taste of the food, 5-stars...but for the slowness of the service, 3-stars, thus the 4-star rating...got a cheeseburger, which was amazing, sloppy but amazing (seems the sloppier the better they taste as far as burgers go). Kids liked their food as well. It took 37 minutes front the time we ordered to when we got our food. worth it if you've got the time... read more

Gotta love an old school drive-in, especially one with very low prices. My sister had heard about this place from locals so while in the area we made a special trip to eat here. Car service (but no squawk boxes) - nice. This old A&W still had many of their traditional items. The food was solid including the mini corn dogs. The root beer in the glass mug was smooth. Just like we remembered. And their malts were top notch for just $3! If I lived nearby I would be here a lot in season. And my doctor would not be pleased! read more

Favorite summer spot! We love eating in our car & having the car hops come to take our order. Our favorites are the papa burger, chicken sandwich & mozzarella sticks. And of course a root beer! Make sure you plan accordingly because the lot fills up quick! read more

I have been all over the USA . There is no better drive in Cheese Burger than Chester's. The ingredients are the best available and the service is spectacular. Put down your phone and go there!! ‼‼‼‼‼‼‼‼ read more

Throwback to the days of Root Beer Drive-In restaurants. Only thing missing are the roller-skates! Glass mugged Root Beer hit the spot for this late night dinner meal. It was unusually warm for an October night in Wisconsin. T-Shirt and shorts weather at night in Wisconsin.... Unthinkable! Sure sign of global warming! Anyhow, waitress/car hop was super nice and actually saved me some $ when I told her to "keep the change" as a tip. She could have easily walked away happy, but she made sure I new it was a $50 that a gave her... Not a $20..... Like I thought it was! I'm a nice guy in all, but not that nice! Now to the food. Onion rings and fries were good but unfortunately our burgers were pretty rare in the middle. I ate mine because I'm a man and that's what we do... But the other burger went to waste. Too bad, because I could tell that this was a good burger, even though it was very pink in the middle. The bun and the toppings were what seemed to be perfect. I will go back because I believe this was just a cooking error not a common theme with the food. That's why I'm still giving them a 4 star rating... Because I know that they are better than tonight's burgers, Should have sent them back but we didn't.... read more

We really enjoyed the cold root beers served in mugs to our car window. The order takers were very attentive and friendly. We visited Chester's several times while in Plymouth...it was that good! read more

Chester's Drive-In - two mugs of coffee on the dashboard of a car - Burgers Near Me - Plymouth, Wisconsin

If you are anywhere in the area, you need to stop at Chester's. My boyfriend who has been coming here since he was a wee child brought me to this 1950's throw back and I could not have been happier to stuff my face with its fried, buttery, cheesy goodness. So by Drive-In, they mean you park in one of about 15 spots where a waitress comes out to your car to take your order. She will probably take her sweet time, so don't head to Cherster's in a hurry. Once you order from a menu posted down the middle of the drive-thru, she brings out a interesting contraption that rests on your window as you rest your beverage on the tray and bring the rest of the food into the car for in lap consumption. I hear the burgers are amazing, but as a vegetarian, I ordered the grilled cheese, fries, fried cheese curds and mozzarella sticks! Impressively after all that I had room for dessert -- which is NOT to be missed. Vanilla and Orange Sherbet combo for the win! It tastes like those popsicles you used to eat when you were younger :) While obviously NOT your healthiest meal, its well worth the calories! And don't forget to use your car time to spy on the interesting characters around you. read more

After a long and tiring fourth of July weekend, my Hubby said that he was hungry for a great juicy and greasy burger. Needless to say, I agreed with him. We scoured the interweb for some great local places and Babe had overhead some of his co-workers talking about Chester's Drive-In. We located some pictures and thought "why not?!!?" So we went on Sunday night. Not surprisingly, we pulled into a full lot. We could barely find a spot!!! The waitress was quick to come to the window. When I say window, I mean car window. This is a drive in after all!! The waitresses were young and very nice, but Babe and I both agreed that they should be on rollerskates. Either way, they were very quick and courteous. After browsing through the extensive menu, Babe decided to order the "Teen Burger." We confirmed with the car hop that these are NOT just for teens. They're for all ages, and thank goodness, because this thing was DELICIOUS with a capital D. I decided to go with the standard cheeseburger. I was not disappointed. It had that charbroiled taste and was just dripped in butter. Like seriously here folks. When I tipped the burger to my mouth it was like a dripping faucet of butter-just how I like it. That brings me to another point. While we received a number of napkins, the stack simply wasn't enough to satisfy our dirty mouths. We had to ask for more!! We tried to get a picture of my root beer float for you all to drool over, but as it was a hot day, the ice cream on top just refused to stay frozen and afloat. It was dripping all over Babe's SUV (luckily he was too busy with his Teen Burger to glance over at me). I wasn't able to get a good shot of it, but as it turns out, someone else was able to snap a picture for the Yelp site, so be sure to check that out if you're interested in seeing what this glass of heaven looks like!!! When we were all done, the car hop came back to pick up our butter-soaked napkins and we praised her for her special service. She walked away with a pretty hefty tip for taking such good care of us (Babe usually tips pretty well when he has a belly full of greasy goodness). When we tried to pull out of the lot, there were so many other vehicles trying to pull in. We almost got rear ended!!! Thankfully Babe used his mirrors and we avoided a catastrophe. We made it out safely and there were no buzz kills to ruin our full stomachs. Here's one last story. Right before we turned back onto the main road, I let out a HUGE belch. read more

Stopped in last night for dinner...per yelp... Not a rootbeer fan, but it was pretty tasty! Just had the Chester's Special, with ketchup & mustard... The fries were great and too many! :) The burger.....meh....ok....wasn't anything Fantastic, but definitely wasn't bad. read more

Chester's is one of the coolest places to eat in Sheboygan County, they are one of the very few drive in eateries we have around the area and the food is simple yet delicious. Hands down the best steak sandwich you can find! read more

Maybe it's a nostalgia thing, maybe it's a small town thing......maybe it's just because there are not a lot of options in Plymouth, but Chester's just wasn't good. It might be good for desserts or root beer floats, but there has to be dozens of better food options in Plymouth. Greasy, small burger patties, cold fries, and too many toppings made this a disastrous choice for dinner. If there isn't a better option in Plymouth, I'll have to make the journey into the big city of Sheboygan for my next meal up there. read more

Had lunch here while on our honeymoon. Great burgers and fries, but the root beer float was the best! read more

Chester's Drive-In - Burgers Near Me - Plymouth, Wisconsin

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Authentic drive in food. I like the teen burger, which is loaded with everything including bacon. I just love it because it's flavorful and fresh. My husband doesn't like it so much because they serve the hamburgers on chewy kaiser rolls, not in the usual soft hamburger rolls like at fast food restaurants. The onion rings are great and so are the fries. If you like root beer, theirs is made at the restaurant. They serve their root beer float comes in a frosty mug. This place is busy, busy, busy in the summer. CASH ONLY! Also, you should tip your car hop. :-) read more

Some of the best burgers and food around. Old time drive in with great service. A must stop if in the area.

Second time here this year and we took the food to go. Both times French fries were extremely soggy, no thanks.

Mediocre food. Server was kind of not good at her job. Wouldn't give us all our food till we paid and then forgot to give us our fourth thing of fries then charged us for them. Didn't apologize just tried to agrue. read more

The burgers here are excellent and the root beer is very good. I also really liked the onion rings. Typically I prefer battered to breaded onion rings but these breaded ones were really good and had lots of onion in each ring. The prices here were also very fair. No credit cards so don't forget you cash. read more

***Revised review. Great prices for excellent food and service. A staple of Plymouth!

If you are in Sheboygan County, Wisconsin and you don't stop at Chester's... Shame on you. The best drive-in I have ever been to. I often crave Chester's and living 1000 miles away in Charlotte, NC, that is a bad thing. It is locally owned and always delivers great food. Is it good for you? Well, it is Wisconsin and burgers, brats, cheese and beer rule. My favorite is the Teen Burger. For a drink/dessert, the Root Beer Freeze - It is incredible and so refreshing. The staff is great and is typically students from Plymouth High but there are many returning vets that come back annually during the summer months when Chester's is open. Do yourself a favor and put this on your list of must visits! read more

Cute little drive in diner. Reminds me of the old A&W drive ins. Great cheese curds and good burgers. Fast food and courteous waitstaff.

Always the best drive-in around. Got the dub bacon cheeseburger American goodness, breaded mushrooms and a chocolate malt! Fantastic! Obviously I recommend this place, only open I think 7 months out of the year and March is about the start of it. Get ya some!!! read more

Family owned and run for decades - Chester's (formerly know as A&W) is an icon in the small town of Plymouth. People have been know to take a Sunday drive in the summer from Chicago to have a burger for lunch. A great example of a "Sheboygan Style" butter burger - thin, grilled (not fried) burger on a sheboygan style hard roll topped with butter. No, that is not mayo on your sandwich - it's wonderful butter that will drip onto the waxed paper wrapper. The rootbeer is served in chilled mugs and made special for the restuarant. Don't forget to tip your carhops - especially on the cold and hot days! read more

If there is any place to go in sheboygan county for a drive in its here! Great malts and burgers with the classic feel of a drive in restaurant make Chester's a great place to eat read more

It's a great drive in experience. Not many places like this anymore. My son wanted burgers as we traveled through town. Great onion rings and crispy fries. Burgers only rated fair. Thin meat and a chewy bun. Make sure to get a great root beer in a frosted mug. read more

Had a deluxe burger which was over loaded with toppings that the very thin burger taste was unrecognizable. The cheese curds were offensive to an self respecting wisconsinite, didn't finish half. Order a steak and cheese was good, excellent rolls. Strawberry and banana shake was good. Novelty of drive in their strongest sell point. Won't be a regular that is surely the truth read more

You CANNOT beat Chester's. Can you find a better burger... maybe. But it's the cheese curds and the root beer that sell it for me! And the feel of driving up to the window. This is one of my all-time favourites. HIGHLY recommend. read more

If you want a a good buttery no frill burger this is your spot. The fries are good and you get plenty. It is a true drive in and only open in summer. A musr stop. read more

It's good, it's definitely not some amazing hidden gem in Plymouth, WI. yet to be discovered by tourists. The place can get crowded, you eat in your car or grab a bench out front. The ice cream is very weak, the prices are okay, and you wind up tipping the servers. So, it's not your cheapest option. The burgers taste really good and the expensive root beer tastes like a fine root beer. I don't like dealing with the hustle and bustle of this place, while the majority of traffic is funneled up and down Eastern Ave out front. It's obnoxious at times; last second turns, braking, accelerating out of the lot, stacking up at the red light in a little 8,500 population town. Not somewhere I have frequented in over a decade. read more

The best cheeseburgers in the world. Start with a Sheboygan County hard roll -- also the best in the world -- then top the burger with ooey-gooey cheese and dripping greasy butter and you have nirvana-in-a-basket. Even the paper it comes wrapped in is worth a lick if not an outright nibble. These burgers will make you whimper, moan and beg for more. read more