9 Midwest Destinations Perfect for Solo Travelers

When it comes to solo travel, the Midwest can satisfy just about every vacation craving imaginable. Are you looking for a diverse imaginative corridor filled with stimulating restaurants and art museums, or a laid-back beach oasis where you can stretch out your toes in the sand? Perhaps you’d prefer a balance of outdoor adventure and city fun. Your next great adventure begins at one of these enticing regional getaways.

Door County, Wisconsin

When you visit Door County, you get a twofer—a down-to-earth Midwestern feel combined with a low-key luxury dining and shopping scene. The area encompasses 70 miles of quaint beach towns on the Lake Michigan coastline, and it’s a getaway in its own right. Sip a glass of Wisconsin chardonnay, join in on a fish boil, visit the famed Cana Island Lighthouse, put on your cherry-picking overalls or kayak at Peninsula State Park.

Minneapolis

No matter what time of year you visit Minneapolis, the larger of the Twin Cities sets the stage for a memorable solo trip with a spectacular theater community, ample green spaces and culinary hotspots. Hop on one of the numerous biking and walking paths that hug the Mississippi and zip around to see the city from a novel perspective. During your stay, don’t miss a chance to grab a seat at the bar of Spoon and Stable and savor James Beard Award-winning chef Gavin Kaysen’s rustic Midwest cuisine. Get your arts fix at Walker Art Center and Guthrie Theater. Or watch the Minnesota Twins play at Target Field, one of the Midwest’s newest MLB parks.

Chicago

Chicago brims with cosmopolitan luxuries, and solo visitors can revel in a chock-full itinerary and still not run out of things to do. Hit up Chicago’s legendary foodie scene, take a walking tour of its local street art, shop at more than 460 stores on the Magnificent Mile, glimpse historic architecture on a 90-minute river cruise, or sip a cocktail ​​watching the steel-framed skyline sunset in a tower observation deck. We promise, you won’t be left wanting for entertainment in the Windy City.

Saugatuck, Michigan

It’s simple to find your place in this artsy little beach town along Michigan’s west coast. Saugatuck looks like the location of a summertime Hallmark movie, the sum total of flourishing galleries, a laid-back pace and grassy dunes off the scenic Blue Star Highway. It’s the sort of charming place that makes you want to dress like Diane Keaton and become a regular at the same restaurant several nights in a row. While you’re here, pick up a few souvenirs along Butler Street, explore Oval Beach or take a class at the Saugatuck Center for the Arts. Stay at one of the restored retro motels or motor lodges. Lake Shore Resort overlooking Lake Michigan puts yoga, bikes, kayaks and trails at solo travelers’ fingertips.

Kansas City, Missouri

Kansas City may be famed for its barbecue and bewildering name (it’s in Missouri, but shares a metro area with Kansas City, Kansas), but there’s so much more to discover. In this riverside metropolis, Midwest nice mingles with Southern charm, historic hotels like the Crossroads spoil guests in style, and comfort food is a staple (KCMO is home to a celebrated taco trail and, of course, plenty of burnt ends). Solo travelers will delight in a variety of cultural attractions, like the Nelson-Atkins Museum of Art, Crossroads Arts District and American Jazz Museum. And speaking of jazz, don’t miss the jazz clubs! Amble through the historic 18th and Vine Jazz District or make a reservation at the Green Lady Lounge, a jazz club with a 1920s speakeasy ambience.

Galena, Illinois

Tucked in the northwestern corner of Illinois just 10 minutes from Iowa and Wisconsin, Galena is a former mining town that’s become the state’s most nostalgic tourism destination. Downtown Galena feels like a scene straight out of the 1860s: more than 85 percent of the town is on the National Register of Historic Places, including the former home of Ulysses S. Grant. The old-world vibes abound, and you can take full advantage by perusing local wineries and distilleries (Blaum Brothers Distilling Company is a favorite), parks, gardens and historic landmarks without straying far from Main Street.

Milwaukee

Milwaukee is a city of confluence in so many ways. Perched on the shores of three rivers, it also serves as a junction of brew culture, outdoor adventure and German heritage. Solo travelers have their pick of waterscapes to explore on foot or by boat, a tough summer festival calendar and ways to enjoy a German brat (there are over 70 sausage varieties at Usinger’s, a fourth-generation local hotspot). Head to the historic Third Ward district for hip boutiques and galleries in 19th-century warehouses, tour Lakefront Brewery and stop by Bradford Beach for an ice cream cone at sunset.

Duluth, Minnesota

Set on the sparkling waters of Lake Superior, Minnesota’s crown jewel has a coastal Norwegian feel. Canal Park, Duluth’s revived warehouse district near the Aerial Lift Bridge, is peppered with shops, restaurants and maritime attractions, including the only all-freshwater aquarium in the nation. Solo travelers seeking green space will appreciate the city’s proximity to nature. Head to Enger Park—one of 100 parks in the city—for a great panoramic view, or stroll the Duluth Lakewalk along Lake Superior and stop to smell the roses at Leif Erikson Park.

Hocking Hills, Ohio

With its towering sandstone cliffs, carpets of wildflowers and hemlock forestscapes, this enchanting corner of Ohio caters to outdoor enthusiasts. Every pocket of this 10,000-acre region feels like a different sort of beauty. Though nature is the main attraction, the local chefs give the Appalachian gorges a run for their money. Stop by The Inn & Spa at Cedar Falls for an eyebrow-raising steak, JimBo’s for homemade pizza in a biker bar and Hocking Hills Moonshine distillery for a stiff drink that tastes like Granny Smith apples.