Midwestern Road Trip: Chicago, Indiana Dunes National Park & Cuyahoga Valley National Park – 2023

While I prefer to be in nature when traveling, I do like exploring cities too! In 2018 Jarrett and I went to Chicago for a long week, primarily to cheer on our friend Colleen running the Chicago Marathon. In October 2023, she ran the Chicago Marathon for the 2nd time. Since we had enjoyed our trip there previously and still had more we wanted to check out, we decided we’d go again to support her at the race, but then spend some extra time in the area. If you’ve been following my blog or Instagram for the past few years, you’ll know that Jarrett and I are on a quest to visit all 63 U.S. National Parks and our vacations usually revolve around them. This visit to Chicago was no different. While we would be in the city part of the time, we decided to also include Indiana Dunes National Park and Cuyahoga Valley National Park in our trip.

Our trip started in Boston – we were on the same flight as Colleen, her husband (and Jarrett’s best friend) Brian and their two daughters. We were happy to lend an extra hand to them – traveling with kids is no joke! When we landed in Chicago, we parted ways for the day. Colleen had to do some race events and prep while Jarrett and I were heading out for our first adventure!

About an hour outside of Chicago lies Indiana Dunes National Park. While it isn’t the most remote or stunning, it is a pretty cool park! We tackled the Cowle’s Bog trail, which wasn’t that difficult (except for where you actually had to walk up the dunes) and it was pretty.



We put our feet in Lake Michigan (freezing) and had some snacks on the beach. It honestly felt like we were in a coastal location like Cape Cod or the Outer Banks. The only downside was that to both sides of us were industrial buildings, which hindered the views. We did love seeing the Chicago skyline in the distance across the lake though! After finishing our hike, we stopped by the visitor center for souvenirs and then returned to Chicago for the night. After freshening up, we walked down to the water to get dinner at Pinched on the River, a great Mediterranean restaurant.


Appetizer plate at Pinched on the River

The next morning, we woke up bright and early to meet up with Brian and the kids so we could find a good spot to cheer on Colleen. Chicago is such a beautiful city, and I always love admiring the architecture there. Colleen had an amazing race; she crushed her personal best by about 10 minutes – and this is after having two kids!! I’m always so impressed by her! Understandably she needed to relax and rest for a little bit but we agreed to meet up later for dinner.



Once we went our separate ways, Jarrett and I went somewhere I’ve been wanting to go for a long time – The Field Museum! Like many kids, growing up I had a big dinosaur phase and for a while I wanted to be a paleontologist, so I was very excited to go see their exhibition, including Sue the T-rex. We explored the Egyptian exhibit, which was also fascinating. I could’ve spend a whole day there, but sadly we only had a few hours.



To finish up our time in the city, we had dinner with our friends and then grabbed a post-dinner beer at Crushed by Giants Brewing Co. Chicago is so beautiful and walkable. I would definitely make another trip there in the future!



The next morning we hit the road early. We stopped at Indiana Dunes National Park to do another hike there – the Dune Succession Trail. It consisted mostly of wooden boardwalks and stairs but there were some sandy portions. The trail is supposedly haunted by the ghost of Alice Mabel Gray, otherwise known as Diana of the Dunes. Alice was an advocate for the dunes, lived on her own in a shanty there in the early 1900s and helped with the preservation of the dunes. Overall it was a pretty quick, easy hike and we were soon back on the road.



Our next stop was Spicer Lake Nature Reserve. I had never heard of this spot but my friends over at Black People Outside (@blk.people.outside on Instagram) posted about it and I thought it looked like a great place to stop. We saw lots of praying mantis and spent about an hour strolling the property. Afterwards, we headed to Crooked Ewe Brewing in South Bend. The beers and food were good but my favorite part was they promoted a local dog rescue and apparently hosted rescue events at the brewery!



We continued our journey to Toledo, Ohio, home of the minor league baseball team, the Mud Hens! Our hotel was overlooking the stadium. It was very quiet in town, and while the small city seemed very clean with many businesses, when we were there, it was almost like a ghost town! Besides grabbing dinner and staying at our motel, we didn’t explore the Toledo area at all. We hit the road early to get to the last place on our itinerary – Cuyahoga Valley National Park!



Cuyahoga Valley National Park is nestled between Akron and Cleveland and is a perfect escape to nature from urban settings. Cuyahoga is very quaint but again, like Indiana Dunes, isn’t as awe-inspiring as some of the other national parks. We did enjoy our time here though and did a few short hikes, my favorite being the Ledges Trail, which had so many beautiful and unique geological features. We spent a full day at the park, which was enough for multiple hikes but not enough time to do a bike ride, which is something I’d definitely be interested in doing if I’m ever back in the area. We left the following morning and while the trip was jam-packed with activities, we still felt like we had plenty of time to relax and explore.



I do feel like I will need to make another trip to the Windy City though so you may read about it again someday soon! If you’ve been to Chicago, tell me your favorite place in the city in the comments below.

📍I acknowledge the lands mentioned in this post are the ancestral lands of the Myaamia, Kaskaskia, Bodwéwadmi (Potawatomi), Kiikaapoi (Kickapoo), Očhéthi Šakówin, Peoria and Erie people.

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