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Midwest 7 Day Road Trip Itinerary – Chicago, Wisconsin, Minnesota

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In 2019 we embarked on a Midwest road trip from Omaha, Nebraska to Chicago, IL, to Sheboygan, WI to the North Shore of Minnesota. Today I’m sharing all the details with links to where we stayed, ate, and played.

Day 1-3: Chicago

Day 1: We hit the ground running and walked all over the city. We stayed at a Marriott and never moved our car. Walking or taking Uber everywhere was much easier.

We made our way to The Bean. We are suckers for the tourist pictures everyone takes.

For dinner we ate at Revival Food Hall where we met up with old friends. If you have followed my blog for a long, long time then you will recognize this face. Revival was so fun and perfect with food court type selections for everyone plus games and entertainment. A low cost meal option was nice too.

Day 2: Architecture Boat Tour River Cruise on Chicago’s First Lady. This was an absolute highlight of our trip. I have never taken so many pictures of buildings. The tour guide was fabulous and we learned things about these buildings and the history we wouldn’t have learned otherwise. I’m not one for group tours or anything guided. However, this was excellent, and I’m so glad we didn’t miss it!

Lunch was at Portillo’s. It was worth all the hype. Our boys loved eating hot dogs with all the unique toppings you don’t see often. Or ever.

The Field Museum was the next stop after lunch. If you love museums, you’d enjoy the Field Museum. We flew through it because none of us are big museum lovers. However, you could spend hours here, especially if you have younger children. I’m still glad we stopped in.

Navy Pier was next where we enjoyed a fun drink and snack at Bubba Gumps. It’s very touristy, but still a fun experience if you’ve never been. Both Navy Pier and Bubba Gumps! If you are a Forest Gump fan, you have to eat at Bubba Gumps at least once in your life. When you need service, you place a Stop Forest Stop sign on your table. If you are all good, keep the sign on Run Forest Run. The peel and eat shrimp soaked in garlic butter is our favorite.

You can’t visit Chicago without having pizza. Dinner was at Giordano’s South Loop.  It was everything you think a Chicago style pizza should be.

Day 3: Our final day in Chicago started with a walk to breakfast at Yolk. Breakfast might be our favorite meal so on each trip we try to find at least one or two great spots for a memorable meal. This picture would be the breakfast my middle son, Zachary, chose. Full of sugar.

We took in an afternoon Chicago Cubs game. I’ve never been more impressed by a stadium. Wrigley Field was so clean and had an old, classic look, yet felt so updated. I don’t even remember who they played, but I loved every second of being at that field.

We packed in everything we wanted with 3 days in Chicago. Next stop Sheboygan, WI.

Days 4-6: Sheboygan, WI

The drive from Chicago to Sheboygan is only a 3 hour drive. So we timed our drive in order to visit the Jelly Belly Factory on the way north. This was such a fun, quirky stop. I’ve recently learned this factory closed. So sad as it was so much fun!

Had we known how much we’d love the Airbnb and Sheboygan, we would’ve stayed more than 2 days. This was a nice change of pace from the city.

The house was spacious and spotless. The views of Lake Michigan were incredible. You walked right out the back door through the yard onto your own private beach. Lake Michigan is impressive. I describe it as a lake that behaves like the ocean.

The house was perfect for our family. My husband loved the record player and selection of vinyls. The boys loved the loft with binoculars and lots of board games, particularly Monopoly. I really dislike that game. They started a game that continued for the full 2 days we stayed here. My favorite part of the house was the backyard and beach. It was so nice to grill, sit around the fire, and watch the moon over the lake. This rental goes down as one of my favorites of all time.

Day 4 we simply enjoyed the home, grilled, and played at the beach.

Day 5 we explored Sheboygan. We walked the paths and enjoyed the views at Blue Harbor Resort. The South Pier District was so quaint! We played mini golf at Harbor Pointe, ate ice cream at South Pier Parlor, kayaked, and simply enjoyed the stroll along the pier.

Next we headed to Kohler State Park and raced up and down the dunes. It was an absolute blast.

Days 6-7: Lake Superior, Minnesota, and the North Shore

Day 6: We woke and began the 6 hour drive before dawn. We started our Minnesota portion exploring in Duluth, MN at the southern tip of Lake Superior. Our first stop was the Lake Superior Maritime Museum. This was informative and interactive. We all enjoyed it.

We stopped at pullouts along the drive enjoying the wildness of Lake Superior. We spent the night in Two Harbors. We wished we had not stopped here for the night. To do it over we would have driven straight up and stayed 2 nights at our final destination, Grand Marais.

Day 7: Gooseberry Falls State Park and Black Beach were both complete treats. We hiked through Gooseberry. It was beautiful. Black Beach was our favorite. We played in the sand and climbed rocks. We slowed down and took it all in.

We made it to Grand Marais, the most adorable harbor village. After checking into our hotel at The Best Western Plus Superior Inn (which we loved because the rooms came with incredible views of the lake), we hit the pavement once again to explore all the town had to offer. I quickly found an adorable bookstore, Drury Lane Books. I almost never travel without visiting a bookstore. Or several.

We ate dinner on the rooftop of one of the many restaurants and went back to the hotel for a good night’s sleep before driving home the next day.

This was a perfect 7 day road trip and I wouldn’t add or take away a single day. My only change to what we did is that I would skip staying in Two Harbor.

The fun is in the discovery and the exploration. The memories you make traveling with the people you love last a lifetime.

 

 

 

 

 

One blip of a moment that showed why simple traditions matter

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In our first year of marriage, Steve played on a church softball team. One crisp Friday night, I sat on the bleachers cheering him on. A group of teenagers surrounded me. They were discussing Friday night plans. We had no children yet, so naturally I leaned in to spy on their conversations.

Lighthearted laughter, bantering back and forth. I smiled. I hope my teens have sweet spirits like this one day, I thought. A girl called out to one of the guys. “Hey, we are all going out to grab something to eat tonight. Want to go with us?”

“Not tonight! It’s Friday. Chicken and rice Friday. I never miss mom’s chicken and rice.”

My heart melted right into those hard as a rock metal bleachers. A teenage boy declining a Friday night out to go home to his mom’s meal. Because that is what Friday nights held in their home.

That was a turning point moment for me as a not-yet-mama.

I saw what I wanted to create in our family. I wanted a connected family. One filled with simple, yet meaningful traditions.

Start with the end in mind.

When an architect draws up a house plan, they ask their client what it is they want. The client will tell them their dream home and what they envision. They may say things like “I want to host large parties. Entertaining is important to me.” And the architect will draw up a plan that includes a design fit for their dreams and ideas.

When building begins, the builder works from the plan. The plan lays out the steps needed to reach the end goal and final result. Each step is intentionally taken to create the vision cast by the client.

In the same way, creating a family culture and establishing connected relationships involves looking down the road and deciding what is most important. Then you make a plan. Not a perfect plan. But. A plan.

With our families, we start with the end in mind too.

 

Here are a few ideas:

  • read aloud together. Start early and keep going when you think they’ve outgrown it. We are never too old to listen to stories. Some of my favorite memories are around books we’ve read together as a family. We’ve laughed and cried and celebrated.  We have a collection of memories around stories. It’s a favorite summer tradition in particular.
  • a simple weekly meal – like chicken and rice Friday. Taco Tuesdays are pretty popular. It’s simply nice to have something to all look forward to together. It’s steady and sure. Taco Tuesday arrives each week without much hurrah. Just a regular meal everyone counts on in a world that often is filled with setbacks and disappointments.
  • family dinners – sitting together to eat is important to me. Creating schedules to make that a priority is hard but worth it. For some families this is exceptionally hard. Try for at least one night a week. Or 2 or 3. Just set what works and stick to it.
  • weekly family night- Pick a night of the week for some family activity. Game night. Movie night. Go get ice cream. Again it’s that repeated activity that everyone counts on and looks forward to.
  • holiday traditions – The simpler the better. You don’t have to consult Pinterest and go over the top. Kids are typically quite pleased with less than we adults realize. It really is about the little things.
  • birthday traditions – My motto is always simple. I have a birthday banner from Zachary’s 5th birthday I saved. I hang it for everyone’s birthday. They all expect to see it when they wake up.

We have so many traditions, but they are super simple. In fact, I’d go so far as to say they are so simple, my kids wouldn’t call them a “tradition”. But to me a tradition is something we repeat together and come to expect we will continue to repeat.

My almost 16 year old son was invited to something recently. When he told me, I quickly said, “Go! You should go.” He responded, “No mom, that night is the same one as our annual tradition. It’s a tradition. I don’t want to miss it.”

And my heart did that melting thing it did some 18-19 years ago as I eavesdropped on teens I didn’t know realizing that I wanted to be a mom who created simple moments and meaningful traditions to foster connected relationships.

Traditions are a reminder of belonging. They connect us one to another.

You may remember I wrote a Christmas devotion titled Seeking Christmas. The heart of the book was to provide families with simple family traditions tied to the true meaning of Christmas. While the book is no longer in circulation, the spirit of Seeking Christmas, along with the ornaments and hide and seek activity, are alive and well.

I created Seeking Christmas to counter the materialism and consumerism of Christmas, while simultaneously creating traditions centered completely around why we even celebrate. My kids rarely remembered a material gift from year to year, but they never forgot the simple moments we built into our holiday season.

It was the experiences and activities they asked for. Not the presents.

So here it is. A 7 day Christmas ornament hide and seek activity. 1 ornament a day you hide, let your kids find it. Then you open the Bible together and read the scripture. Over 7 days you unfold a small part of the Christmas story.

It’s simple. It’s effective. It’s a tradition. It’s for the busiest of busy families. It’s made to stand alone or build upon however you choose. It’s flexible. You don’t have to start on a certain Sunday or December 1st.

You can buy the download to create your own ornaments for $1. I will also be loading some printed, ready to ship ornament sheets on the shop so stay tuned for those. I only have a few sets leftover from my recent Pop-Up shop. So grab them while they are here.