Kenosha's streetcars

Couples Getaway – 2 day Itinerary for a trip to Kenosha, WI!

After seeing my Kenosha adventures and pictures, several people have requested itinerary suggestions to plan their own visit!  So I will be giving my suggestions in itinerary style for: Couples Getaway, Girls Weekend, and Family Fun daytrip.  See below for the 2 day Couples Getaway itinerary!

Kenosha is a city in Southeastern Wisconsin with a population of roughly 100,000.  It is located:

45 minutes from Milwaukee
1 hour & 10 minutes from Chicago
2 hours from Madison 
2 hours & 30 minutes from Green Bay

*This is the itinerary that my husband and I followed when we were in Kenosha.  We kept things pretty busy, but if you’re looking for a little more chill time, it’s easy to skip some of the suggestions and stay longer somewhere else!

Couples Getaway (2 days & 1 night)

Day 1

Jelly Belly Visitor Center (Pleasant Prairie)

A stop at the Jelly Belly Visitor Center is fun for any age, and I consider this a MUST VISIT when you’re in the area!  They recently opened a new exhibit, and improved the free train ride through the warehouse.  You get to learn all about how the famous candy is made, and the history of the Jelly Belly Candy Company.  Plus, there is a sample station in the Candy store, so you can be sure to know which flavors to buy for later!  Or, you can get a bag of “Belly Flops” which are awesome.  They are the Jelly Belly jelly beans that didn’t make the final cut.  Some of these candies are stuck together, or not the right shape, but they all still have the amazing flavors that we know and love!

Jelly Belly Visitor Center - Candy Shop
Stocked up on Belly Flops!


Lunch at Waterfront Warehouse

Fun atmosphere and delicious food!  We ordered the Tijuana Rolls for an appetizer, which were amazing.  I tried the flatbread with goat cheese for my meal, and it was so tasty.  There were a lot of other amazing choices on the menu, it was hard to choose what to order.

Waterfront Warehouse - Kenosha, WI


Visit The Civil War Museum 

This museum is very well done and has multiple exhibits.  Be sure to plan your visit so that you can catch the 360 degree movie “Seeing the Elephant” which is played on the hour.

Civil War Museum - Kenosha, WI


Shopping at Mars Cheese Castle

Sample cheese, and shop for Wisconsin merchandise such as cheese, wine, and beer, as well as clothing and accessories.  Also, be sure to try a famous grilled cheese sandwich!  You get to pick what type of bread, and TWO types of cheese for the sandwich.  It also comes with a choice of potato for a side, and a pickle spear.  The cheese curds are amazing too.

Mars Cheese Castle - Kenosha, WI

Hang out at PUBLIC Craft Brewing Co.

PUBLIC Craft Brewing Co. was one of our favorite places we visited in Kenosha.  Very chill environment and great beer, it’s a nice place to hang out and relax!  We loved playing shuffleboard, and just hanging out.  They had a lot of board games, and even a giant Jenga up front.

PUBLIC Craft Brewing Co.

Dinner at House of Gerhard

This restaurant opened in 1964, and is known for its excellent German-American Cuisine.  I ordered the “German Platter” which was on special the night we went, and also a German beer.  Everything was amazing, and there was SO MUCH FOOD, which made for some great left-overs!  All dinners are served with muffins (these were my favorite), German hardrolls, as well as Garlic toasts& Liver Pate.  But wait!  There’s more…. also a relish salad, as well as a choice of soup or salad (I ordered the salad with the blood orange dressing), and a choice of potato!  Our waitress was very friendly and the atmosphere was nice.  It’s a great place for a nice date night dinner.

  • Closed on Sundays

House of Gerhard - Kenosha, WI pinterest   House of Gerhard - Kenosha, WI


Stay overnight at Double Tree by Hilton (right next to the outlet mall!)

We really enjoyed our stay at the Double Tree.  The room was very spacious, the bed & pillows were so comfortable, and I can’t even tell you how excited I was to use the hot tub!  The pool and hot tub area was very clean, and we were the only ones down there at the time.  There is also a nice exercise room (which has a window that looks into the pool room) that we didn’t end up using, but would have had we been at the hotel longer.

Double Tree by Hilton - Pleasant Prairie, WI


Day 2

Breakfast at Choo-Choo Charlie’s

This is a Train themed restaurant that is part of the train station!  Yes, kids love this place for obvious reasons, but it is still a lot of fun to eat at as an adult.  Everyone was very friendly, and it’s a unique restaurant because the meals are delivered in baskets behind a toy train!

Choo-Choo Charlie's train delivering food

Pleasant Prairie Premium Outlets

*This isn’t the most efficient order to do shopping at the outlet malls, since Choo-Choo Charlie’s is closer to the museums and afternoon activities.  But, since the outlet mall doesn’t open until 10:00am, if you want to shop there it requires a little extra driving.  If you have time to squeeze shopping in when you’re at the hotel anyways (even the night before) that’d be better.  Otherwise you could eat breakfast at the hotel (not included) and then go shopping at the outlets before checking out of the hotel and heading to the museums.

To me it was worth going to both Choo-Choo Charlie’s and the mall so we did a little extra driving to make it all work.  Since my husband was along, this was a very quick shopping trip!  It’s so close to the hotel, that it’s worth a visit, even if you only make it to a couple stores.


Visit the Kenosha Public Museum

Great exhibits, but especially cool to see the exhibit about the two mammoths that were excavated in Kenosha County!

  • Check out my adventures at the Kenosha Public Museum (& 3 other museums in Kenosha!)
  • *This museum is next door to The Civil War Museum, so you could rearrange and do the two together, if you aren’t on information overload.  I like to split up museums so I enjoy them more.  Personal preference though.

Kenosha Public Museum


Lunch at a drive-in

I love eating at a classic drive-in restaurant, and Kenosha has a few, one of which we tried, and the others listed I would like to try in the future

  • The Spot Drive-In
    • Cash only
    • Food was classic for a drive-in, and very tasty.  Great root beer and banana splits (big enough to share) but service felt rushed so I’d be curious to try one of the other drive-in’s on my next visit to Kenosha.

The Spot Drive-In

Ride the Electric Streetcar

Did you know that Kenosha has a running Electric Streetcar Circulator?  Seriously, how cool is that?  These restored streetcars (also known as trolleys) are an interesting way to experience a little bit of history as you ride along the 2-mile loop.  We got onto the Streetcar outside of the Joseph McCarthy Transit Center, and rode the full loop.  Not only is the streetcar ride entertaining on its own, the route it travels includes gorgeous views of Lake Michigan, and also passes by some of the Museums (among other things).  It’s a nice way to get another look at the beauty of Kenosha.

We rode on the streetcar midafternoon on a Wednesday, and were the only riders for all but one block of the loop.  But, it was pretty funny because as we were leaving the Dinosaur Discovery Museum a little while later we spotted the streetcar as it drove past and it looked nearly full!

Electric Streetcar - Kenosha, WI

Although riding the loop in a streetcar doesn’t take very long (it was about 10-15 minutes when we rode it), it is something you should do at least once!  Climbing onto the streetcar and sitting in the seats, it’s hard not to feel thrown back in time.  There is such charm to not only seeing a beautifully maintained streetcar, but it is a whole new world to hop onboard and ride one!

  • Hours vary by the season, and are greatly reduced in Winter (January & February)
  • Bring exact change for fare (at the time of this post: $1 per ride for those 13+, 50₵ per ride for those ages 5-12, and free for 4 years old & younger, but as always with tourist attractions prices are subject to change in the future)

Visit the Dinosaur Discovery Museum

This museum is fairly small, however they do a great job fitting a lot of information and displays into it.  Neat place to stop and look around, and it’s free(donations are appreciated).  Plan on maybe 20-30 minutes there unless you’re very into Dinosaurs.

Dinosaur Discovery Museum - Kenosha, WI

Explore & hike around Petrifying Springs Park (a 360 acre park with several trails)

This park was so beautiful to walk around.  We were there at the tail end of the fall colors, but everything was still so gorgeous (I can only imagine how stunning the area must be during its fall prime!).  There were so many bridges that were great for photographs.  While we were there, we saw a couple having a photo session in the park, what a great location!  The Pike River offers a great backdrop, not only for photos, but also for an afternoon picnic.  We hiked around for an hour or two in the park, but easily could have stayed longer.

Petrifying Springs Park - Kenosha, WI

Visit the Kenosha History Center

Another nicely done museum in Kenosha, where you can view artifacts up close and learn about the history of the city and the businesses that have contributed to Kenosha as it is today.

Kenosha History Center
Kenosha History Center

Shop at Modern Apothecary

A pharmacy with a wide variety of essential oils, bath products, and cute Kenosha & Wisconsin souvenirs.  Neat store to look around at, and a perfect place if you’re looking for a gift for someone.

  • Closed on Sundays

Modern Apothecary - Kenosha, WI

Dinner at Villa D’ Carlo

Open since 1957, Villa D’ Carlo is a family owned restaurant that is particularly famous for its thin crust pizza.  Although the pizza sounded delicious and tempting, the second I spotted Fettuccini Alfredo (with broccoli) on the menu I knew my order!  Our waitress was friendly and service was prompt.

Not long after placing our orders, a relish tray with a bean salad, and a pasta salad was brought out along with a basket of bread.  Both dishes were great, but I seriously could have eaten an entire meal of that pasta salad, it was amazing!  Next our soup/salad came out.  I ordered the soup of the day which was incredible.  Once our dinners came out we had already had a lot to eat so needless to say, I had some wonderful leftovers to take home.  We were told that the Tiramisu here is really good too, so I was hoping to have room for dessert but didn’t this time!  Looks like we’ll just have to go back again, and try the famous pizza and save room for some Tiramisu.

  • Closed on Tuesdays

Villa D' Carlo - Kenosha, WI


We had such an awesome time visiting Kenosha.  There is so much more to see and do in the area than I realized before planning this trip.  Hopefully you can use some of the information from our trip and the suggested itinerary to create your own amazing Kenosha adventures.  Happy planning!

Have you been to Kenosha?  What are your favorite things to do there?  Comment below!

Don’t forget to pin this for later:

Kenosha, WI 2-day itinerary for couples Kenosha, WI 2-day itinerary for couples


Disclaimer: Our visit to Kenosha was hosted by the Kenosha Area Convention and Visitors Bureau.  We received overnight accommodation, and gift cards for our meals and activities.  However, all opinions are my own.


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