Best Midwest Fall Road Trips

Mary Korte
3076 days ago.

I love to travel and I really love to fly, except this time of year. In late September and October, it almost seems like a sin to fly. You miss all the gorgeous colors of the fall and the trees changing. Fall is undoubtedly my favorite time of the year and I am sure many of you concur! It is a great time to add a day or two of vacation to your weekend and get the heck out of dodge and take a road trip! Living in the Midwest, we have some great opportunities within a (fairly) short drive from St. Louis and Southern Illinois. Pack the weekend bag, fill up the gas tank, crank up your favorite road trip music, and let’s see what might be a cool weekend of fall color: lake 1

Lake of the Ozarks

This is a no brainer for all the St. Louis folks out there. Depending on when you go, this could be considered off peak season and you can get a great rate on a timeshare, house share, or a great hotel. Hate the outdoors? Hit the outlet mall or spas and get some serious therapy time, retail or otherwise.

Wine Trails

Whether you like Augusta, Hermann, or the Shawnee Hills Wine Trail, it all ends up with a good bottle of wine and some great music overlooking the countryside. Stay at a bed and breakfast or make it a day trip. Regardless, it is time well spent relaxing with friends. Check out more about the wine in Chrissy’s recent blog post.

Bike the Katy Trail

Amazing views, awesome B&B’s and wineries dot the landscape. You can hit it hard and power through as a test of your biking prowess, or rent a bike part way there and just take a leisurely ride. Heck, drive it if you want. Regardless of your preference, it’s beautiful scenery. Check out their website for organized rides or to plan your personal trip.

Some of my favorites are a bit more of a drive. Let’s start with the Illinois/Missouri border and move north from there:

The Great River Road

Head up to Alton and keep going north! Hike Pere Marquette Park, spend an afternoon at Fast Eddies Bon Air, or head north to Hannibal and hang out with Mark Twain and Becky Thatcher’s ghosts in Hannibal, MO. There isn’t a bad view any time of the year.



Always a favorite among the weekend getaway set! Stop in and see my friends at Massbach Ridge Winery’s tasting room on Main Street or at the vineyards. Need to get your antique on? Galena was voted part of the “10 Best Antiquing Towns In The US” by Fodor’s. Into history? Galena was a big deal back in the day and the height of society before Chicago. Take the guided trolley ride around town and find out where all the famous people lived! For more info, check out the visitor’s bureau website. or my previous blog about the homeland.

For a longer road trip, go hang with our friends in Wisconsin or Iowa:

Door County, Wisconsin

There are a few requirements for this trip. 1. Plan ahead to get a good hotel. 2. Book next year’s reservations before you leave. You will love it that much! Time on Lake Michigan doesn’t get much better if you like light houses, works by original artists, and a good fish boil every now and then.

Wisconsin Dells

Too cold to take the kids swimming but they are dying to go? Want adult fun and maybe some golf? Head up to the Dells! The resorts are full of indoor water parks where the price is included in your stay. Personal favorite?  Chula Vista Resort-great water park, fabulous golf course, tons of entertainment in the Dells! Chula Vista also offers amazing suites that can sleep up to 12 people complete with full kitchens, fireplaces, and hot tubs in each. The only one problem you’ll have if you stay there is that you will never want to leave!

Cranberry Harvest

Almost half of the nation’s cranberries are grown right in Wisconsin! Check out the Warrens Cranberry Festival the weekend of September 25th in Warrens, WI. I would probably stay in the Dells and drive up for the day. How many times do you get to stand in a cranberry bog?



Madison County, Iowa

Remember The Bridges of Madison County with Clint Eastwood and Meryl Streep? Check out the real bridges just south of Des Moines. It’s a romantic little ride from Columbia or St. Louis. A great place to try your hand at photography and creating your own artwork. Their 46th Annual Covered Bridge Festival is October 10-11 this year.

THE BRIDGES OF MADISON COUNTY -- NBC Theatrical -- Pictured: (l-r) Meryl Streep as Francesca Johnson, Clint Eastwood as Robert Kincaid -- Photo: Warner Bros.
THE BRIDGES OF MADISON COUNTY — NBC Theatrical — Pictured: (l-r) Meryl Streep as Francesca Johnson, Clint Eastwood as Robert Kincaid — Photo: Warner Bros.

Whatever your destination is during these lovely fall weekends, sit back and enjoy the ride and the beautiful scenery.

Photo credit: & Galena Visitor’s Bureau

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Mary Korte

Mary is a proud farm girl with some city attitude and mom of a sports dude in training. She loves travel, sports, food, wine and combining all of that with family and friends!

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