By Katy Spratte Joyce
June 14, 2020
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Editor’s Note: Travel might be complicated right now, but use our inspirational trip ideas to plan ahead for your next bucket list adventure.

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 Midwestern road trips, which are sure to highlight the best of America’s pulsing, vibrant heartland.

Great River Road, Wisconsin (Prescott to Kieler)

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The picturesque city of Prescott, situated where the pristine 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 the 250-mile-long 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, as it’s the brick-and-mortar location for James Beard Award nominee Lisa Carlson and her partner, Carrie Summer. If you can, sit outside on the lovely back patio.

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 for over four decades. Menu winners include the Alaskan halibut with black butter caper sauce and the flavorful roasted chicken that comes with nearly 20 full roasted garlic cloves. While there, try some of the famed Spotted Cow beer from Wisconsin’s own New Glarus Brewing Company (only available within the state). 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 southern terminus of the road. The Great River Road ends in small Kieler, Wisconsin, near Iowa’s pretty river city of Dubuque.

Best of Indiana (Lake Michigan to Brown County)

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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 laid-back fare, consider the Boathouse Restaurant. Spend the night just two hours south at The Alexander in downtown Indianapolis, both the capital and largest city in the state. Explore the city using the refurbished 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, rock climbing, and more.

Sandhills, Nebraska (Grand Island to Alliance)

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Begin your journey in Grand Island, an area that truly shines in the spring with the world’s largest sandhill crane migration. From there, follow State Highway 2 to Broken Bow, where you can access information on the route at the Sandhills Journey Scenic Byway Visitor Center. Thirsty travelers can imbibe at Kinkaider Brewing Company, which offers a taproom and restaurant in the gateway to the Sandhills. Then, continue on Highway 2 until you reach the town of Anselmo, where you’ll take a slight detour to Victoria Springs State Recreation Area, an oasis known for its healing mineral waters. Here, road-trippers can enjoy activities like paddleboarding, fishing, and picnicking at one of Nebraska’s oldest state recreation areas. In the summer season, the park’s log cabins make for a fun overnight option and can be reserved up to a year in advance. Pro tip: If you opt for an overnight, be sure to check out the stars without the usual light pollution interference. End at perhaps the quirkiest attraction on this list, Carhenge, a replica of England’s Stonehenge crafted with old cars. Bonus: For those who want a taste of the Oregon Trail, consider a journey to the Chimney Rock National Historic Site, less than an hour beyond Alliance.

Beginning of Route 66 (Chicago, Illinois, to St. Louis, Missouri)

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Route 66, which runs from Chicago, Illinois, to the Santa Monica Pier in Los Angeles, is a classic, and you can explore a portion of it in the Midwest. Start in the Windy City, after enjoying some of its famous deep-dish pizza. Additionally, you may want to stop for a photo op at the corner of Michigan and Adams, where the historic “Begin Route 66” sign stands. Then, head to nearby Wilmington to see one of the famed Muffler Men statues, the Gemini Giant, near the charming Launching Pad restaurant. From Wilmington, it’s a roughly two-hour drive to the Illinois capitol of Springfield, where history buffs will want to check out the numerous Abraham Lincoln sites. Highlights include the Lincoln Home, his Presidential Library and Museum, and the Lincoln Tomb. Next, journey onward to St. Louis. Travelers can stretch their legs at the famous Chain of Rocks Bridge, which has since been turned into part of the Route 66 Bikeway. The bridge is even on the National Register of Historic Places. End your intro to Route 66 in luxe fashion with an overnight stay at the surprisingly affordable Four Seasons Hotel St. Louis, just steps from Gateway Arch National Park. The property boasts a tasty eatery with a James Beard Award-winning chef as well as a full spa. Plus, it's close to another must-visit St. Louis attraction: the incomparable City Museum.

North Shore, Minnesota (Duluth to Grand Portage)

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This drive follows the scenic State Highway 61 for 150 miles along Lake Superior’s stunning, rocky shores. Part of the Arrowhead Region in northeast Minnesota, this drive belongs on any U.S. road trip bucket list. Begin in Duluth, Minnesota, which is famous for its breweries and native Bob Dylan, who was born in the city and raised in nearby Hibbing. Walk along Bob Dylan Way for a glimpse of the folk music legend. Consider sipping some artisan spirits at Vikre Distillery, which offers views of the famed Aerial Lift Bridge. To pay homage to the region’s Scandinavian roots, sample Vikre’s aquavit, also known as “Norwegian Everclear.” For an overnight stay, consider checking Airbnb options in pretty Two Harbors; this town is an excellent base for exploring Gooseberry Falls, Minnesota’s most visited state park, and Split Rock Lighthouse, one of the most photographed spots in the state. Road-trippers should also plan to fill up on pizza at longtime favorite Sven and Ole’s in Grand Marais. From roughly May to October, intrepid explorers can consider an extension to Michigan’s remote and gorgeous Isle Royale National Park. Daily ferry transport is available from Grand Portage, Minnesota, the scenic end point of this North Shore excursion.

South Dakota (Sioux Falls to Spearfish)

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Begin in the state’s largest city, Sioux Falls, with a walk around pretty Falls Park. Then, drive to nearby Mitchell, just over an hour away, to visit the quirky and fun attraction that is The World’s Only Corn Palace. From there, it’s a roughly four-hour trip to the Crazy Horse Memorial, which is the biggest mountain carving on Earth and has been under construction for decades. Outdoorsy types will also enjoy South Dakota’s largest state park, Custer State Park. Travel to the carved faces of Mount Rushmore, South Dakota’s most-visited attraction, on part of the infamous Peter Norbeck National Scenic Byway, then explore Badlands National Park before ending in Rapid City. Here, you can stop in the state’s oldest-operating brewery, Firehouse Brewing Company, for a cold beverage and live music. For those who want an additional taste of the winding road, consider some time on the Spearfish Canyon Scenic Byway. Plus, the ever-enchanting kitsch of historic Deadwood beckons travelers; even though it’s super-touristy, everyone should visit at least once. Additionally, visitors can see some gorgeous waterfalls, hiking paths, and rock ridges in Spearfish Canyon, which is actually more ancient than the better-known Grand Canyon. Pro tip: The back patio at Flanagan’s Irish Pub in downtown Spearfish is a relaxing way to end your road trip. Also, try the well-awarded brews at Spearfish Brewing Company.

Upper and Lower Peninsula, Michigan (Sault Sainte Marie to Leland)

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Begin in the small town of Sault Ste. Marie, perched between Lake Superior and Lake Huron and adjacent to its Canadian sister city of the same name. Be sure to sample the Laker Gold beer at Soo Brewing Company, shortened to Soo Brew by locals. Also check out the “lynchpin of the Great Lakes,” the Soo Locks, except from January through March, when they are closed for repairs.

Road-trippers should then head over to Michigan’s second-largest state park, Tahquamenon Falls State Park, which boasts over 40,000 acres of pristine wilderness, including one of the largest waterfalls east of the Mississippi. For an overnight option to break up this trip, stay at the historic Grand Hotel on carless Mackinac Island. Be sure to build in time to try some of this destination’s famous fudge, too. The charming island can be accessed via ferry from Mackinaw City (Lower Peninsula) or St. Ignace (Upper Peninsula). After experiencing some of the delights of the Upper Peninsula, cross the world’s third-longest suspension bridge, the Mackinac Bridge, to Michigan’s Lower Peninsula, which everyone calls "the mitten" for its shape.

Consider a nighttime visit to nearby Headlands International Dark Sky Park, where you just might catch a glimpse of the elusive northern lights. At the very least, enjoy a brilliant display of stars there. From the preserve, it’s just a two-hour winding lakefront drive to Traverse City, known as Michigan’s foodie capital, where you should stop and eat at the French-inspired Patisserie Amie. Sweet tooths, cap off your meal with a stop at the wildly popular Grand Traverse Pie Company. End your trip on the gorgeous Leelanau Peninsula, Michigan’s answer to Wisconsin’s storied Door County. Check out Leland’s Fishtown, take the ferry to the Manitou Islands (part of Sleeping Bear Dunes National Lakeshore), and imbibe at the wineries on the Leelanau Peninsula Wine Trail.