The Midwest may be called Flyover Country, but make no mistake, this region is gorgeous from the ground. Miles of sun-kissed farmland and crystal clear lakes frame the view out your dash while some of the slower scenic routes—from the rolling Flint Hills of Kansas and Ozark mountains in Missouri to the tranquil covered bridges of Indiana and thundering waterfalls in Minnesota—can be seen just off the exit ramp. No matter if it's a week-long journey around the rocky shores of Lake Superior or a quick day trip to a local state park, the United States' middle corridor has plenty to offer outdoors enthusiasts and backyard explorers alike. Here, the most magical Midwest road trips to get your wheels turning.
1 | Duluth to Grand Portage State Park, Minnesota
ShutterstockStart: Duluth, Minnesota
End: Grand Portage State Park, Minnesota
Distance: 145 miles
From Duluth, drive Highway 61 beside the rocky beach of America’s largest Great Lake, Lake Superior. The trip up Minnesota's North Shore is short—just under 150 miles—but there’s plenty to see. If it’s summer, explore the beaches with black sands (Black Beach) and pink pebbles (Iona’s Beach), or pull over at Gooseberry Falls State Park to take a dip in the pool at the base of a spectacular waterfall or hike the 18 miles of trails. There are several other panoramas along the way, including your last stop at Grand Portage State Park by Canada’s border—as well as gorgeous views via a two-mile gondola ride in Lutsen. Pro tip: The funky city of Grand Marais is a good place to bed down for the night.
2 | Badlands to Black Hills, South Dakota
ShutterstockStart: Badlands, South Dakota
End: Black Hills, South Dakota
Distance: 130 miles
The Badlands has an otherworldly feel to it thanks to its multicolored peaks and vast volcanic rock landscape. It's worth it to go slow and take your time meandering down the 40-mile scenic byway (SD 240), especially during dusk when the national park turns molten gold and dusty pink. From here, continue on to Rapid City for an overnight before exploring the Black Hills National Forest the next day. This 1.2 million-acre region is home to some of America's must-see sites—looking at you, Mount Rushmore and Crazy Horse Memorial. Further north beyond Sturgis, Bear Butte State Park is a beautiful place for a hike, and a sacred spot for Native Americans.
3 | Route 66, Illinois
ShutterstockStart: Chicago, Illinois
End: Collinsville, Illinois
Distance: 300 miles
Route 66 is one of the quintessential American road trips, and no chapter of it is so charming—and underrated—as its path through Illinois, where there’s enough retro kitsch to give you Instagram content for days. The Mother Road begins at the Route 66 sign on E. Jackson Boulevard in Chicago. You'll meander 300 miles south to St. Louis, passing 1940s diners, antique stores, gas stations, and drive-in movie theaters straight out of a vintage advertisement. Pro tip: Keep an eye out for the almost 30-foot-tall Gemini Giant in Wilmington, Illinois.
4 | Milwaukee to the Wisconsin Dells, Wisconsin
ShutterstockStart: Milwaukee, Wisconsin
End: Wisconsin Dells
Distance: 121 miles
Kick off the journey in Milwaukee, Wisconsin's brewing capital, where you can tour the MillerCoors Brewery and Pabst Mansion, the former 19th-century home of Pabst Brewing founder Captain Frederick Pabst. Then, three hours northwest, the Waterpark Capital of the World is the perfect family-friendly getaway. A few of the Wisconsin Dells parks merit superlatives: America’s largest outdoor water park (Noah’s Ark), America’s largest resort water park (Wilderness Waterpark Resort), and America’s largest wave pool (also at Wilderness Waterpark Resort) lie along your route. However, the outdoors activities in the area make it an autumn and spring destination, too: Be sure to stop by the Wisconsin Deer Park, where kids can feed Wasa crackers to free-roaming deer.
5 | Flint Hills, Kansas
ShutterstockStart: Flint Hills, Kansas
End: Wichita, Kansas
Distance: 190 miles
The 190-mile trip through the endless undulations of the Flint Hills is a spectacular sight almost any time of year, though spring and fall show the colors at their best. Soak up the scenery at the 11,000-acre Tallgrass Prairie National Preserve outside of Strong City, or take a detour on Rte. 901 to visit the 8,600-acre Konza Prairie research preserve. Head another two hours south to arrive in Wichita, Kansas’ largest city that features craft breweries, a Frank Lloyd Wright house museum, and striking street art in the Douglas Design District.
6 | Parke County, Indiana
ShutterstockStart: Tangier, Indiana
End: Bridgeton, Indiana
Distance: 55 miles
Indiana’s Parke County winds through 31 covered bridges, making it a spectacularly scenic drive—especially in October, when the Covered Bridge Festival draws local artisans, craftspeople, and farmers to showcase their produce and goods during peak fall foliage. Make sure to look out for the horse-drawn carriages frequently spotted in the countryside as well as the 19th-century general stores, mills, and log cabins in small towns like Mansfield and Bridgeton. For a quirky place to stay, head to the Old Jail Inn, where you can spend the night in a converted cell.
7 | Historic Hills Scenic Byway, Iowa
ShutterstockStart: Moravia, Iowa
End: Donnellson, Iowa
Distance: 110 miles
This route is full of historic sites, including Iowa’s oldest courthouse and the state’s only Civil War battlefield. But this area of Iowa also boasts three state parks, including a resort state park. It’s worth taking a couple days to drive the 110 miles of the highway, since there’s so much to do, from fishing on the River Water trail and canoeing in the Lacey-Keosauqua State Park to checking out the 100-plus Amish and Mennonite businesses around Drakesville and Bloomsfield.
8 | US 12 Heritage Trail, Michigan
ShutterstockStart: New Buffalo, Michigan
End: Detroit, Michigan
Distance: 180 miles
For one of the Midwest’s quirkier road trips, head to the US 12 Heritage Trail, a.k.a. “Michigan’s Largest Garage Sale.” Admittedly, you’ll have to time it right—the sale happens over a long weekend in August each year—but it’s worth clearing your calendar for. Over three days, vendors line a 180-mile stretch of highway from New Buffalo to Detroit selling everything from antiques to homegrown vegetables. And no, the “heritage trail” distinction has nothing to do with Americans’ love of a good bargain: It refers to the ancient Native American trail the highway now covers (even further back, it was a part of a mastodon corridor, which drew the indigenous people who hunted them).
9 | The Ozarks, Missouri
ShutterstockStart: Sullivan, Missouri
End: Lake Ozark, Missouri
Distance: 310 miles
With about 310 miles of routes and eye-popping side trips, Missouri’s beautiful Ozark mountains, forests, and lakes offer up a bounty of natural attractions. Explore the Onondaga Caves, the remnants of a sea that once covered the region, camp in the 1.5-million acre Mark Twain National Forest, or bear witness to history at the Indian Trail Conservation Area, which includes a stretch of the Trail of Tears.
10 | Minnesota River Valley Scenic Byway
ShutterstockStart: Blakely, Minnesota
End: Ortonville, Minnesota
Distance: 287 miles
This 287-mile trip is a highlight reel of Minnesota's rivers and waterfronts. You can see it from behind the steering wheel, or make a pitstop and hike the trails in the six state parks that intercept the byway. The area has a rich history as homeland to the Dakota people, whose name for the area is “Mni Sóta Maḳoce” (“the land where the water reflects the sky”); learn about their traditions and history at the Lower Sioux Agency. There are also farm museums, historical homes, and Minnesota’s oldest brewery, August Schell Brewing Company.
11 | Antique Alley, Indiana
ShutterstockStart: Richmond, Indiana
End: Knightstown or Portland, Indiana
Distance: 80 miles
Antique Roadshow lovers should make a beeline to the so-called “Antique Alley” of eastern Indiana, an 80-mile loop where more than 1,200 antique dealers have set up shop. The Historic Richmond Depot District, a thriving neighborhood in Richmond with some great restaurants, is worth an afternoon lunch stop to fuel up before the shopping spree. Choose from two different trails: Trail one takes you from Richmond west to Knightstown via the Historic National Road U.S. 40, then back to your starting point on SR 38. The star attraction: Cambridge City, with two blocks of shops including 13 antique stores. Trail two takes you north from Richmond to Portland on US 27, with 25 antiques shops dotting the roadside.
12 | Lake Superior Circle Tour
ShutterstockStart: Duluth, Minnesota
End: Sault Ste. Marie, Michigan
Distance: 1,300 miles
If you have a week or two of time, take the long way around Lake Superior on the Circle Tour, a 1,300-mile stretch of gorgeous shoreline in Wisconsin, Ontario, Minnesota, and Michigan. Mid-June is a great time to catch festivals before summer’s peak tourist season begins, but if you’re willing to risk a chill, late September is ideal for seeing the leaves change. Don’t have quite that long? Any of the individual state segments merit a vacation of their own.
