7 Best Midwest Road Trips in the US

Flyover country it is not. The Midwest offers a variety of landscapes, ripe for exploration with a classic road trip. From rolling vineyards to lush river valleys, high limestone bluffs to some pretty great lakes, this region of the United States is often overlooked. It’s time to change that, so cue up a playlist, pack your favorite snacks, and hit the road on one of these top Midwest road trips, which are sure to highlight the best of America’s pulsing, vibrant heartland.

Wisconsin’s Great River Road

Start: Prescott, WI
End: Kieler, WI
Length: 234 miles

The picturesque city of Prescott, situated where the St. Croix River meets the Mississippi River, makes for a great jumping-off point for this road trip. Start at the Great River Road Visitor & Learning Center and drive south along Wisconsin’s 250-mile stretch of the National Scenic Byway, which hugs the Mississippi’s curves and bluffs. In addition to pretty views, this area of Wisconsin offers unexpected culinary delights in tiny river towns. Bay City’s Chef Shack is worth a stop for its lovely back patio and two James Beard Award-nominated chefs at the helm.

Pepin, Wisconsin, located on the widest natural part of the river — the aptly named Lake Pepin — also deserves some attention. There, check out the Harbor View Cafe, which has been impressing visitors since 1980. Meanwhile, fans of the “Little House on the Prairie” books can visit the birthplace of writer Laura Ingalls Wilder, a roughly 10-minute journey inland from Lake Pepin. Continue along the beautiful highway past La Crosse, Wisconsin, then, consider cutting inward to Viroqua, Wisconsin, via State Highway 14. The rolling hills and pastureland of Vernon County are home to the highest concentration of organic farms in the state. Visit the Driftless Cafe, home to another James Beard Award nominee, for the best farm-to-table fare in the region.

Wine lovers should consider hitting some stops on the Great River Road Wine Trail, especially Danzinger Vineyards on the bluff in Alma. Those who prefer a hoppy beverage can stop at the Potosi Brewery near the end of this road trip. The Great River Road stretches beyond Wisconsin, but Kieler is the last stop before it crosses the border and continues on to Iowa’s pretty river city of Dubuque.

With a total driving time just under five hours, this trip could be done in a day, but most of the attractions are right at the start. A nice way to break it up into a two-day trip is with an overnight stay near the vineyards.

Indiana’s Natural Wonders and Small Towns

Start: Indiana Dunes National Park, IN
End: Bloomington, IN
Length: 288 miles

Begin at the 15,000-acre Indiana Dunes National Park in northwestern Indiana. Situated on Lake Michigan’s beautiful southern shore, this area is perfect for birding, beach time, and other activities in nature. From there, drive to the small lake town of Winona Lake to browse the little shops along the waterfront. For an upscale bite, stop into Cerulean, and for more laidback fare, consider the BoatHouse Restaurant. Spend the night two and a half hours south at The Alexander in downtown Indianapolis, both the capital and largest city in the state.

Explore the city using the Canal Walk, visit the acclaimed Indianapolis Children’s Museum, scope out some street art, and enjoy a meal at St. Elmo Steak House. For an extra dose of exercise in the city, check out the Monon Rail Trail, a former rail line that stretches from Indy to the northern suburbs. After your time in the capital city, head south to Bloomington, home to Indiana University. This college town offers both a picturesque campus and a walkable downtown area. Continue on to Brown County State Park, the largest in Indiana, which is open for picnicking, hiking, horseback riding, and more.

You’ll be on the road for at least five hours on this trip. Considering that you will want a day or two for exploring all Indianapolis has to offer, the trip should be broken up into two legs at least.