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September To Do in the Upper Midwest: A Guide to Exploring the Region

The Upper Midwest is known for its picturesque beauty, vibrant culture, and unparalleled outdoor recreational opportunities. September is an especially magical time of year in this region, as the leaves start to change colors and the air becomes crisp and cool. Whether you're a local looking for new adventures or a visitor eager to explore the area, there are countless activities and attractions to enjoy throughout the month of September.

1. Discover the Beauty of Northern Michigan

No trip to the Upper Midwest is complete without a visit to Northern Michigan. In September, the region's natural splendor truly shines. Take a drive along the Tunnel of Trees, a scenic route lined with colorful foliage, and stop by Mackinac Island for a taste of old-world charm. You can also explore the Sleeping Bear Dunes National Lakeshore, which offers stunning views of Lake Michigan and miles of sandy beaches.

2. Attend a Fall Festival

September is festival season in the Upper Midwest, and there are plenty of events to choose from. Head to Oktoberfest in La Crosse, Wisconsin, for beer, brats, and live music, or check out the Duluth Fall Festival in Minnesota for arts and crafts, carnival rides, and a parade. For a more unique experience, attend the Corn Palace Festival in Mitchell, South Dakota, where you'll see elaborate murals made entirely out of corn.

3. Explore Chicago's Cultural Scene

Chicago is a cultural hub, and September is an excellent time to experience the city's diverse offerings. Visit the Art Institute of Chicago to view works by iconic artists such as Vincent van Gogh and Pablo Picasso, or catch a show at one of the city's renowned theaters, like the Steppenwolf Theatre Company or the Chicago Shakespeare Theater. September is also the month when the Chicago Jazz Festival takes place, so be sure to check out some of the free performances in Millennium Park.

4. Go Apple Picking in Wisconsin

Wisconsin is famous for its apples, and September is prime apple-picking season. Visit one of the state's many orchards, such as Door Creek Orchard or Eplegaarden, to pick your own apples and enjoy other fall activities like hayrides and corn mazes. You can also indulge in apple cider donuts and other seasonal treats.

5. Take a Road Trip Through the Great Lakes Region

The Great Lakes region is home to some of the most beautiful scenery in the country, and September is the perfect time to take a leisurely road trip. Start in Cleveland, Ohio, and follow the coast of Lake Erie up through Michigan, stopping to admire lighthouses, visit charming small towns, and take in the stunning fall foliage. End your trip in Milwaukee, Wisconsin, where you can sample the city's famous cheese and beer.

A scenic view of the Tunnel of Trees in Northern Michigan
A scenic view of the Tunnel of Trees in Northern Michigan
A view of the Duluth Fall Festival in Minnesota
A view of the Duluth Fall Festival in Minnesota
A person picking apples at an orchard in Wisconsin
A person picking apples at an orchard in Wisconsin
Michigan's fall foliage, apple picking in Wisconsin, fall festivals in the Upper Midwest, exploring Chicago's cultural scene, road tripping through the Great Lakes region, September travel ideas

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