10 fall road trips from Chicago

September 1, 2023

Fall road trip season is here, and it’s my favorite time to explore new Midwest towns! There are so many places under 4 hours from Chicago to visit for changing leaves, things to do, yummy food to eat, and places to see. Below is a list of my favorite road trips from Chicago and think are great this time of year!

Saugatuck, Michigan

One of my favorite road trips is to Saugatuck, Michigan! Maybe the best time of the year to visit is fall. In fact, it’s the only time we have been! It’s beautiful! It’s about 3 hours away from Chicago, and there is so much to do. There are dune rides (for slightly older kids), beaches, lots of great restaurants, ferry rides, shops, and art galleries! There’s Crane’s Orchard, where we apple-picked, went on small rides, did a corn maze, etc. We even hiked the Saugatuck Dunes with both kids, and the trails are pretty easy. I have two full blog posts here- for families or a couples trip to the area!

Galena, Illinois

Another favorite getaway is Galena, and it’s the perfect fall road trip. The town was founded in 1826, and all the history and nature set the perfect backdrop for autumn. Plus, Galena goes ALL OUT for Halloween! Their annual Halloween parade is the largest in the Midwest and will occur on October 28, 2023. We have done it, and it’s very fun! Oktoberfest is on September 30, and the Galena Country Fair is on October 7-8.

It’s an easy drive – just a little over 3 hours from Chicago with lots to do and see. We have stayed at an Airbnb or the townhomes at Eagle Ridge Resort, which is then a short drive to downtown. But they do have a shuttle service during Halloween weekend (or at least used to!).

Grab a coffee at one of the cafes on the main strip, like Trolley Depot Coffee, and take the trolley on a scenic, historical tour of Galena, where you’ll see many of the original early nineteenth-century buildings. You can do yoga with or take a walk with goats and then shop the small boutiques & cafes that line the main streets. I love Bread and Vine for breakfast, brunch, or lunch, Isabella Ltd for gifts and home decor, Bloody Marys at Fried Green Tomatoes, and Poopsies for toys and gifts. The last time we went, we had lunch at Durty Gurts Burger Joynt, and it was delicious with great service and so fun!

Rockford, Illinois

Rockford, Illinois, is just about 100 miles northwest of Chicago. We love to walk through and see the 12 acres of gardens, waterfalls, ponds, and tea house at the Anderson Japanese Gardens. This is BEAUTIFUL in the fall with the changing leaves. Perfect fall road trip. They do close on October 31st, so make sure you go before then!

When you’re ready to fill your belly, head over to The Norwegian, which is only a 3-minute drive from the Gardens. Don’t skip the Danish pancake balls and housemade jam! Walk off your meal and shop next door at the cutest midcentury modern shop, Rooted, for gifts and home decor. 

If The Norwegian’s menu isn’t kid-friendly enough, try Beef-a-Roo, a counter service small chain of restaurants serving burgers, chicken sandwiches, salads, and more. We also loved the fresh food at the American restaurant Magpie, and the coffee and vibes at Inzombia Coffee

If you’re traveling with kids, you can’t go wrong with the Discovery Center Museum. If you are a member of any Illinois children’s museums, you can get into this one for free! It’s especially great for ages 5-12, with lots of hands-on STEAM activities and an amazing gated outdoor play structure with views of the river!

Another super cool place to visit is the Midway Village Living History Museum! First, you’ll enter a huge warehouse full of fascinating Rockford and American history. Did you know that sock monkeys were invented in Rockford, and the largest sock monkey in the world is in this museum? Once you’ve navigated through the indoor section, head out into an actual village with early 1900s replicas of a general store, a one-room schoolhouse, a town jail, a doctor’s office (my kids couldn’t stop talking about the medical history they learned), and other buildings. In each of these buildings, a costumed volunteer provides more detail and answers questions. I honestly thought my kids would think it was super boring, but they LOVED it! We could have spent so much time there.

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is SO close to Chicago, which makes it such an easy fall road trip day! MKE serves up great restaurants with lots of shopping! You can brewery hop or walk around downtown. If it’s a cooler day, visit the Public Market for some wine while you shop for cheeses, breads, etc. Lakefront Brewery is also popular, and you can sit outside on their large patio. Visit Broadway Paper (paper and gift store) and MOD GEN (gorgeous plants), and then brunch at the popular and delicious Sweetdiner! This can be done in a day or stay for the weekend! I’ve taken the Amtrak there, and it’s such an easy ride!

Sawyer & Three Oaks, Michigan

Located just outside New Buffalo, MI, Sawyer and Three Oaks are such cute towns! You can do a whiskey tasting at Journeyman Distillery. We thoroughly enjoyed the full tour of the beautiful grounds. There are small pumpkin farms and bakeries along Arrowhead Highway (Swedish Bakery is so good!), and we love stopping at Sawyer Garden Center. It’s right next to Greenbush Brewery, which is great for tastings. We love their food, and they have an outdoor area! Either stop by Indiana Dunes or the Galien River County Park, which is pretty cool for taking long walks! The trees are just beautiful!

Starved Rock & Matthiessen Park, Illinois

I recently went to Starved Rock, Illinois, and had the best time! It’s about 2 hours away from Chicago and a pretty easy road trip! It’s great for hiking with or without the kids. I would recommend taking older kids, though, because part of the trail is pretty difficult. It took about one hour each way to complete one hike. Then, there’s a restaurant we grabbed lunch at on the top of Starved Rock. It was pretty good and had pretty views of the canyon!

I haven’t been to Matthiessen, but I had so many suggestions after I posted Starved Rock to check it out. It’s close to Starved Rock, apparently less crowded, and the trails are easier for kids!

You can also stop by the town of Utica on your way out, and it’s so cute! It’s small, but there are cute shops and wineries to check out.

I have stayed at Camp Aramoni, which is not far from Starved Rock. These are tents that are totally built up on the inside with several beds, air conditioning, a bathroom, and more! I would say this is much more of a luxurious type of trip and pricey. They do book up fast! I think it would make a fun girl’s trip to split a tent!

Holland, Michigan

Holland, Michigan, is just the cutest little town! There’s so much to see and do between the dunes, the beach, the tulips, and the windmills! It’s definitely an even better place to visit in the fall, too! Downtown Holland has many great restaurants and shops. Don’t miss Lemonjello’s for college shop vibes, coffee, and pastries, The Holland Peanut Store, an old-school candy shop, Neli’s Dutch Village, a Netherlands theme park with a great gift shop, and Deboer Bakery for amazing cronuts. For dinner, we love New Holland Brewery, Boatwerks (the only waterfront restaurant in town), and Beechwood.

Marquette County, Wisconsin

Manny and I did this trip together, and to our surprise, we really had such a great time! I worked with Travel Wisconsin on this project, and I am so thankful! This is a very, very small county in Wisconsin, about 3 hours away from Chicago, just outside of Madison. We stayed at Lake Arrowhead Campground. This is nothing fancy! You can tent or rent a trailer, ours was really nice! It’s in a completely wooded area close to water. There were wild turkeys, hens, deer, etc. In the fall, I bet it’s beautiful with all the changing leaves. Make campfires, go to Wisconsin Supper Clubs, check out Amish country (one of the best bakeries I’VE EVER BEEN TO was on this Amish farm!), and really unplug surrounded by nature.

Oregon, Illinois

We took a family road trip to Oregon, Illinois, a few years ago in September and stayed at the Pine Creek cabins. They are fairly big, come with a firepit and a grill, and sit on a pretty big area of land. These are log cabins across from White Pines State Park, and they are so pretty to hike among the changing leaves! There is a playground for kids, and there are different leveled trails from easy to difficult. Check out the Bison at Nachusa Grasslands, where you can see Bison roam free. It’s pretty cool! There’s really not much else to do but disconnect and be outside!

Hobart, Indiana

I am including Hobart, Indiana on the list for two reasons. There is an apple orchard (County Line Orchard) and a pumpkin patch/produce farm (Johnson’s Produce Farm). You could literally do all the fall activities in one day. We did Johnson’s Farm and then visited the town of Valparaiso, which is maybe 20 minutes away. It’s got cute shops and restaurants. There’s Four Father’s Brewery and a winery, too! You could totally spend a full day doing all of this.

Hopefully, some of these have inspired you to hit the road for fall road trip season! If you need other fall things to do, check out my fall bucket list here!


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