Favorite Midwest Road Trips

I love the Midwest. I was born here, raised here, and it’s here where I gained my love for travel. My family has always had the travel bug, and we often explored towns closest to us as our family vacations. Once I started traveling and branching out on my own, naturally I chose to explore this region first. I haven’t been everywhere of note in the Midwest quite yet, but I have amassed a list of my favorite Midwest road trips that are tried and true. If you’re in the Midwest and are looking for a fantastic weekend trip, these destinations would fit the bill perfectly. Without further ado, here they are:

Milwaukee, WI – An easy hour and a half drive up Route 94 from Chicago, Milwaukee is the perfect place for a quick weekend getaway. Between the lakefront, the breweries and the amazing restaurants, you’re in for a treat. When we were there last summer, I fell in love with the Milwaukee Art Museum, Lakefront Brewery and the Milwaukee Public Market.
Warren Dunes, MI – The Warren Dunes (not to be confused with the Dunes in Indiana, which in my opinion are not as pretty) are a short-ish (2 hours) drive from Chicago. The State Park is beautifully maintained and makes for a lovely day at the beach. Bring a blanket and a picnic to make a day out of it, and if you want to spend the night, you can camp in the park as well.
Starved Rock/Matthiessen State Parks, IL – Speaking of camping, you can hike one or both of these parks in one weekend, especially if you camp near by like we did. Both parks are completely stunning, but Starved Rock offers a little more in terms of trails and lodging. Matthiessen State Park is a hiking wonderland filled with inventive bridges over streams and beautiful canyons. You can do either as a day trip as well, if you’re strapped for time.
Cedarburg, WI – Taking a trip to Cedarburg is like going back to a simpler time. It’s a super cute town just north of Milwaukee with super cute restaurants and shops. We visited this lovely destination after Kayaking the Milwaukee River and had fantastic burgers at Morton’s Wisconsin Restaurant. I’ve been trying to plan a weekend trip here ever since.
Grand Rapids, MI – It’s no secret that I love Grand Rapids; it’s one of my favorite cities in the U.S. It has all of my favorite things: breweries, antique stores and a great live music scene. I’ve been there twice in the past two years and each time we’ve found new reasons to love it. It’s an excellent choice for a fantastic weekend away.
St. Louis, MO – While St. Louis is a little bit longer of a haul from Chicago, it is definitely worth the trip. It has history, (more) breweries, baseball and beautiful parks. I had such fun time exploring this fun city, and I can’t wait to go again to hit the spots I missed. I would recommend going to a Cardinals Game, the City Museum, Delmar Loop and Four Hands brewery.
Galena, IL – Galena is wonderful. There’s no other way to put it. The city is nestled in between hills and the Galena River and has a rich history, being the home of Ulysses S. Grant. The Helluva Half Mile is a stretch of shops, restaurants and bars and runs right through downtown Galena. Pick any of the great B&Bs (I would recommend the Lamberson Guest House) in the area to stay for a weekend away and you’ll be in for a treat.
Lake Geneva, WI – Growing up, we spent many summer weekends cruising around Geneva Lake in Lake Geneva. Besides housing one of the best lakes in the Midwest for boating and swimming, the town of Lake Geneva also has some super cute hotels, restaurants and stores. Plus, it’s just an hour and a half drive from Chicago, which makes it a convenient weekend or day trip. My favorite part of the city is the trail around the lake, which is a peaceful walking path from which you can view all of the very large and very beautiful houses on the water.