10 Fall Road Trips from Chicago

Fall road trip season is here, and it’s my favorite time to explore new Midwest towns! The weather can be great until mid-October! 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!

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!