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Seven Midwest Cities to Explore this Year

A new year brings new opportunities for exploration! One thing I continue to appreciate is that you don’t have to go far to escape.

Here are a few cities that are an easy drive from Chicago and offer lots of fun activities for a day of activities or weekend away.

St. Charles, Illinois

woman sitting on park bench on the Fox River
Downtown St. Charles, IL

Downtown St. Charles, Illinois, is a lively, vibrant urban oasis and offers many things I appreciate having easy access to in Chicago. There are beautiful parks, trails, great restaurants, breweries, entertainment, and water activities, all within walking distance.

St. Charles, Illinois, is located right on the scenic Fox River, about 35 miles outside Chicago. If you want to ditch the car you can hop on the Metra at the Ogilvie Transportation Center in Chicago. It’s a little under an hour trip to the Geneva Stop, which is only 2 miles from Downtown St. Charles, Illinois.

Milwaukee, Wisconsin

There’s more to Milwaukee than beer. It’s a vibrant city that’s good to visit at any time of year. Museums, art, lake activities, historic architecture, music festivals, incredible food, and more await.

We discovered an abundance of options while exploring the city. Even after several visits we’ve only scratched the surface.

Kalamazoo, Michigan

I lived for a brief time in Kalamazoo while a teenager. The city is far different from what I remember.

Kalamazoo, Michigan, has world-class brewing, dining, parks, music, art, theatre, and culture. The city has a heavy focus on arts and entertainment; evident in a downtown was abuzz with live theatre, music, craft markets for shopping, and maker’s spaces for classes and experiences. 

The city also has a rich history. There are 5 historic wards in Kalamazoo with landmarks, buildings, and stately homes showcasing various architectural styles along tree-lined streets. Kalamazoo county was a stop on Underground Railroad. The home that was a safe house, the Dr. Nathan Thomas House, is available for tours by appointment.

Saugatuck, Michigan

A two-hour ride from Chicago along the Lake Michigan coast sits the charming town of Saugatuck, Michigan. Named in the top 10 of Best Coastal Small Towns in 2019 by USA Today, Saugatuck is buzzing with gorgeous art galleries, fantastic eateries, eclectic shops, and beautiful beaches. Also, there’s an assortment of quaint Bed & Breakfasts and boutique hotels to enjoy a cozy and relaxing stay.

Hamilton, Indiana

Named after Alexander Hamilton, Hamilton County is about 30 minutes north of Indianapolis, Indiana. Its largest cities consist of Carmel, Noblesville, Fishers, and Westfield. The county as a whole and cities within have received numerous national accolades, including safest cities in America.

Within the cities of Hamilton County, visitors will find public art and galleries, hiking and bike trails, unique local shops, incredible food, museums, and lots of nature and outdoor activities such as golfing, kayaking, and boating.

LaCrosse, Wisconsin

My husband and I stopped in Lacrosse on our way home from a South Dakota roadtrip. I enjoyed our brief visit so much, I decided I was definitely returning. 18 years, later I made my way back and my visit did not disappoint.

Lacrosse sits on the banks of Mississippi river. The historic downtown offers unique shops, lively entertainment, museums and art galleries.

I suggest staying at the Charmant; a luxury boutique hotel in downtown La Crosse. The building is a renovated candy factory, constructed in 1898 and is on the site of the very first building in La Crosse. I also highly recommend dining at Lovechild, the food is phenomenal!

Three Oaks, Michigan

Three Oaks, Michigan, named after its massive oak trees, is around 52 miles from Chicago in Harbor Country.

Inside the city with a population of less than 2,500, you’ll find art galleries and studios, restaurants and bakeries, a range of shops, including a butcher shop that’s a National Historic Site, a distillery, and the Acorn and Vickers theatres. Plenty to enjoy a full day of activities.

Be sure to visit Froehlick’s bakery and restaurant for incredible food and sweet treats. There’s also wineries, breweries, and sandy beaches within close proximity to the city.

Have you visited any of these Midwest places? Let me know your thoughts in the comments.

This entry was posted in: Midwest

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