Small Towns
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Get Off the Beaten Path and Explore These 24 Underrated Small Towns in the Midwest

The quilt of the Midwest landscape is stitched with small cities and towns that are too often overlooked for the bigger stops, like St. Louis, Chicago, or Minneapolis. But a closer look at a map reveals a world of underrated small towns, each with its own unique allure.

I grew up in the Midwest in a St. Louis suburb. My mom didn’t like to fly, so our summer vacations and spring breaks took us to the nooks and crannies of the Midwest within driving distance.

Before I knew it, my adolescent eyerolls turned to excitement with each small town we approached. In fact, plotting out our next road trip was half the fun. Now, I get to do it with my own family.

Here are some family-friendly ideas for underrated Midwest towns to explore on your next getaway:

Grand Marais-Minnesota
Grand Marais | photo via johnny_myhers

New Ulm | Minnesota

Faster than you can say, “Sprechen sie Deutch?” you fall in love with the German heritage of New Ulm, Minnesota, just 90 minutes outside the Twin Cities. As the City of Festivals, there’s always something happening in New Ulm.

The Midwest is dotted with towns that “Willkommen” you, but New Ulm ups the ante by calling itself “The Most German Town in America.”

Follow the sound of the Glockenspiel clock to the historic downtown before or after dining on cheese curds, spaetzle, brats, or beer cheese at Rathskeller at Turner Hall. Flandrau State Park offers four seasons of outdoor fun, from a beachy swimming pond to winter cross-country skiing. Anglers will love the catfish and walleye found in area lakes.

Grand Marais | Minnesota

Grand Marais captivates with its natural beauty tucked between the north of Lake Superior and Superior National Forest’s Sawtooth Mountains.

The accolades for Grand Marais keep piling up; Budget Magazine named it one of America’s Coolest Small Towns, and Travel & Leisure tagged it as America’s Best Small Lake Town.

Grand Marais is one of the few towns with access to Isle Royale National Park, America’s most re-visited national park. Boundary Waters Canoe Area Wilderness beckons nearby too, and raging rivers and challenging trails fit the space between, with Outside Magazine ranking it as one of the Top 10 Beach Getaways.

Grand Marais is as much for outdoor lovers as it is for artists, with eclectic shops and scenic views along the shoreline.

Ashland | Wisconsin

Across Lake Superior near the Apostle Islands National Lakeshore, Ashland is another lakefront town oozing with charm and outdoor adventures. Visitors get the outdoor escape of their dreams while still being connected to the lively Ashland city scene on the shore of Chequamegon Bay.

Be sure to grab a gallon of pure aquifer water from the Maslowski Beach Artisan Well.

Each season brings a new filter in Ashland, from fall colors that pop to windsurfing on ice in winter through the long summer days of lakefront fun. Paddle the water or take a boat cruise, then lose those sealegs walking through the murals before soaking in the sunset.

Chippewa Falls | Wisconsin

If this name sounds familiar, it’s likely because Chippewa Falls was Jack Dawson’s hometown in Titanic. Summer brings out the crowds to Lake Wissota (which, coincidentally, wasn’t even created until five years after the Titanic sank) and the Irvine Park Zoo.

Walk the fall colors at Area 178, or wait a few months to go walking in a winter wonderland. Adrenaline seekers can even see the town from thousands of feet above with Skydive Wissota.

Enjoy the history of the area while checking out the local breweries and wineries. There’s a waterfront seat for you at one of several restaurants on the Chippewa River. Would you really be in the Midwest if you didn’t have the option of a Supper Club?

The holiday season lights up Irvine Park too with more than 100,000 holiday lights set among cross-country skiing trails.

Holland | Michigan

You don’t have to cross the pond to get a lakeside experience of Holland – just head to West Michigan. The city is right on Lake Macatawa, which connects to Lake Michigan. There’s even Windmill Island, which features the country’s only authentic working Dutch windmill.

Named for the Dutch heritage in town, spring blooms with millions of tulips and the annual award-winning Tulip Time Festival. Walk through an authentic Dutch village or the Holland Museum for an immersive history experience.

Don’t worry about the inconvenience of snow storms. Holland designed snow-free technology that helps clear the streets and sidewalks of winter weather while keeping the winter aesthetic.

Summer brings beach days on Lake Michigan, with the famous Holland “Big Red” Lighthouse standing out on the shoreline.

Sault Ste. Marie-SS
Sault Ste. Marie, Michigan I photo credit: Thomas Barrat / Shutterstock

Sault Ste. Marie | Michigan

Why settle for one small town getaway when you can have two on either side of the border? On the U.S. side is “The Soo” of Michigan’s Eastern Upper Peninsula. The northern edge is Sault Ste. Marie, Ontario, Canada.

The Soo brings a big city feel to a small town, with a technological prowess you can watch as the Soo Locks transition boats between Lake Superior and the lower Great Lakes. Never before has watching a 1,000-foot freighter been so mesmerizing. Several shipping museums tell the story of how the locks work too.

Downtown Sault Ste. Marie stakes its claim as the oldest Midwest city. The core of the historic district is downtown, and nearby Water Street offers a glimpse of historic homes. The peak tour is the Point Iroquois Lighthouse, open year-round with views 72 steps up.

Yellow Springs | Ohio

Visiting Yellow Springs, Ohio, is worth it for its vibrant arts scene, picturesque nature, and unique small-town charm. In fact, Budget Travel called Yellow Springs one of the 10 Coolest Small Towns. Plus, it’s home to Ohio’s oldest tavern at Ye Olde Tavern Trail.

With eclectic shops, cozy cafes, and colorful street art, it offers an inclusive atmosphere. Outdoor enthusiasts can explore Glen Helen Nature Preserve’s trails with several waterfalls, including the iron-filled location that led to the name Yellow Springs.

Civil rights activist Coretta Scott King attended Antioch College here, and the city has a strong connection to civil rights activism. Overall, Yellow Springs provides a refreshing escape full of culture, nature, and community spirit for visitors of all ages.

Waynesville | Ohio

Whether you’re hungry or like history, Waynesville has both things covered. It’s known as the “Home of the Ohio Sauerkraut Festival” and the “Antiques Capital of the Midwest.” Another bragging point for locals is that Waynesville pre-dates the creation of Ohio.

Walking through the quaint downtown, you get a dose of Americana meets an old English village where more than a dozen antique stores mix in with boutiques and restaurants.

Stretch your legs with a ride on the Little Miami Scenic Trail, or head to Ceasar Creek State Park, which has a lake and miles of trails, including one that goes through the gorge. The Ceasar Creek Nature Preserve and Wildlife Area is worth visiting too.

Waynesville is also tucked off the main highway between Dayton and Cincinnati, offering a great day getaway or an easy weekend escape from a big city.

Shipshewana | Indiana

The third largest Amish population lives in LaGrange County near Shipshewana which means you better arrive hungry. Amish farms surround this small town of less than 700 people.

If you’ve never enjoyed the homemade baking, crafts, and woodwork of the Amish and Mennonite communities, this is the place to immerse yourself in the culture. Enjoy scenic drives between locations and look for the barn quilts that dot the landscape. You can also hop on a bike down the Pumkinvine Trail to explore Elkhart, Goshen, and Middlebury.

When you work up an appetite, three stops on the Indiana Culinary Trail are right in Shipshewana.

NOTE: Respect the wishes of the Amish and Mennonite communities. Don’t take pictures of the people, either up close or from a distance. What a great reason to unplug for the entire trip!

Nashville | Indiana

More than 260 miles north of Nashville Tennessee, this iteration of Nashville is better known as an art colony than a musical city, but you’ll still hear sweet sounds emanating from businesses in the historic downtown.

Located in Brown County, “Little” Nashville is also referred to as the “Artist’s Colony of the Midwest” due to its numerous art galleries, studios, and craft shops. Famed artist T.C. Steele spent the latter part of his life here at his home — now a designated state historic site.

When you really want to get away, take the winding country roads to the Story Inn, touted as being “One Inconvenient Location Since 1851.”

Nearby, you can explore Charles C. Deam Wilderness, with more than 35 miles of trails and access to Monroe Lake. Remnants of buildings used by natives and settlers can be found throughout the landscape.

If the wilderness is a bit too remote, the “Little Smokies” can be explored at Brown County State Park. A leaf-peeping trip here in the fall competes with anything the Great Smoky Mountains offers without any of the crowds.

Galena Historic District-Galena, Illinois
Galena Historic District | photo via that_kwc

Galena | Illinois

It’s not too often that Illinois and “scenic views” are in the same sentence outside of Chicago, but Galena has a view over three states atop the Horseshoe Mound Preserve

The view from Main Street sparks nostalgia, with beautifully restored 19th-century buildings housing boutique shops, art galleries, restaurants, and charming bed and breakfasts.

Day trippers will love the convenience of the Galena Trolley, which wraps up all the major historical sites in one trip. One of those stops is the home of Ulysses S. Grant, a gift upon his return as a hero after the Civil War.

One of the best parts about visiting Galena is the truly unique experiences, from hiking with goats to carving your own spoon to custom-designing your own perfume. Galena is now on my summer bucket list for underrated small towns in the Midwest.

Oglesby | Illinois

When you can’t swing a trip to the Grand Canyon or the narrows of Zion National Park, check out Oglesby, Illinois, and nearby Starved Rock State Park. Nearly 20 canyons and 14 waterfalls form a rare collection in the Midwest — the result of a glacier flood about 15,000 years ago.

Rafting on the Vermillion River gives the same excitement as the Colorado River, with sharper curves than the larger river. It’s also one of the only rivers that flowers from south to north in the U.S. The waterfalls in this region fall from high above as if you were in a convertible cave.

Oglesby’s slogan is “Where Friends and Rivers Meet,” and this is a family-friendly destination with the putt-putt appeal you would find in Branson without the crowds.

Decorah | Iowa

Visiting the “Driftless Area” doesn’t sound exciting until you realize what that means. As a section of the country skipped by the Ice Age, its location and firm bedrock resisted any influence by glaciers. It also left behind an ice cave that is open at your own risk. Talk about a cool place — ice lasts into late summer!

The rolling hills and deep-cut rivers spark the outdoor lover in all of us, but more adventure unfolds, and not always in a way that connects dots. Travelers can visit one of the homes where Laura Ingalls Wilder lived or immerse themselves in the Norwegian culture.

Shop among more than 100 stores or belly up to the bar for a local brew. You might need a drink after looking at the pre-historic 6-foot scorpion fossil. Be sure to stand in the very spot where the Decorah Impact Crater slammed into Earth 465 million years ago.

On your way in or out, take a ride on the Driftless Area Scenic Byway, especially during fall.

Amana Colonies | Iowa

Join the communal history of seven colonies dating back to 1855 in eastern Iowa. German settlers escaped persecution to set up their hamlet of communities before turning to a for-profit business model that evolved into the Amana Corporation brand of household appliances.

Guided tours lead visitors to explore the different colonies and a visit to the Amana Heritage Society reveals more of the community’s history too. There’s a festival for every season and a 21-mile trail connecting four of the villages.

The Amana Colonies burst with artistic flair, including influences from Grant Wood, creator of American Gothic painting. Several wineries cross the landscape, with a colonial trend of sweet fruit wines to offer.

Meals lean heavily into German fare in the Amana Colonies, with options for family-style seatings or pub-style snacks and drinks.

Carthage, Missouri
Carthage, Missouri | photo via passenger.side.window

Ste. Genevieve | Missouri

With a strong European heritage, Ste. Genevieve (GEN-uh-veeve) claims its place on the Mississippi River — one of the oldest this side of the banks.

Ste. Genevieve National Historic Park preserves the history dating back to 1735. The buildings and homes are open for guided tours, but it’s the smell of the rose garden that lures you outside. Make sure to stop by the Centre for French Colonial Life for a further glimpse into the region’s history.

The Levee Trail is a great way to stretch your legs after a road trip, spanning 3.5 miles along the river and taking you back to the center of town. Ste. Genevieve is also known for its wineries, including one inside a cave.

Summer vacations in the Midwest are muggy, but River Rapids Waterpark offers a chance to cool off. The lazy river, the lap pool, or the long way down water slide keep everyone in the family busy.  While you’re in this historic town, don’t miss a meal at the Anvil Saloon & Restaurant, serving up specialties like country-fried steak and toasted ravioli.

Carthage | Missouri

While others head to the Ozarks or the crowds of Branson, take a detour in southwest Missouri to America’s Maple Leaf City in Carthage. You’ll find so much to learn here among the tree-lined streets with a lot of fun packed in.

Four national historic districts offer walking and driving tours, all available to do at your own pace. At night, take in a film under the stars at the 66 Drive-In Theatre, which opened in 1949. Stay in the historic Boots Court Motel (ask for #6 or #10 – Clark Gable stayed in both!)

Add this tour to your Route 66 100th anniversary celebration, as the Mother Road goes right through town. A few miles outside of town is Red Oak II, a community of restored buildings that is more art than history. The creator filled it with nostalgia dating back to the 1850s through the Route 66 era, and now the eight people who live here keep the dream alive.

Be sure to stop at the George Washington Carver National Monument, where you’ll go “nuts” for the history of the Peanut Man, who gave so much to science beyond his peanut fame.

Abilene | Kansas

The name Abilene might draw images of the Wild West and Texas tall hats, but the Kansas version is actually ranked as the Best Small Town to Visit in the U.S. for three years in a row!  You could even call it a field trip as one of the Best Historic Small Towns by 10Best.

FUN FACT: The Texas town was named after THIS Abilene.

With convenient access right off I-70, you can swing by the hometown of President Dwight Eisenhower, see the world’s largest belt buckle, and experience the Wild West at Old Abilene Town. Just be glad Wild Bill Hickock isn’t roaming these streets anymore!

Missing your dog on vacation? Visit the Greyhound Hall of Fame. Tired of driving? Let the engineer take you on a historic train tour. Top off the trip with a visit to one of the Eight Architectural Wonders of Kansas at the Seeyle Mansion.

Colby | Kansas

Known as the Oasis of the Plains, Colby, located in western Kansas, gives a nice break from the cries of “Are we there yet?” If I-70 didn’t run through Colby, you might never have heard about it. However, the location in northwest Kansas, near Colorado and Nebraska, makes a great HQ for regional stops.

In Colby, you can visit the Prairie Museum of Art & History, the newly remodeled B.R.O. Motorcycle Museum, or the visitor center built around a grain bin.

Less than 30 minutes away, explore the Buffalo Bill Cultural Center for more Wild West fun. The Fick Fossil & History Museum range from displays of pioneer’s sod houses to ancient shark’s teeth.

Add-on adventures include the Kit Carson County Carousel in Burlington (Colorado), Fort Wallace Museum in Wallace, and perhaps one of the best-kept Kansas secrets at Little Jerusalem Badlands State Park (without the crowds of the badlands in the Dakotas).

You’ll be amazed at how much western Kansas has to offer when you know where to look.

Valentine | Nebraska

You’ll fall in love with Valentine Nebraska, for its daytime activities, but it will steal your heart at night even more. This small town near the border with South Dakota is surrounded by some of the darkest skies in the Midwest, perfect for stargazing among the sandhills.

I’ll be the first to admit that I thought Nebraska was so flat you could see the curve of the Earth, but moving here changed everything. Valentine offers easy access to the Niobrara National Scenic River, with rafting, hiking, and waterfalls to enjoy.

Valentine and Cherry County take you home, where the buffalos (bison) roam through 72,000 acres on the Valentine National Wildlife Refuge. Explore the ups and downs of the Sandhills, visit McKelvie National Forest, or drive through the Valentine National Wildlife Refuge.

However you work up an appetite, you’ll get an amazing steak dinner at places like the Peppermill or grab food to go at Old Mill Bulk Foods before you head out to see the blanket of stars overhead. We recommend Merritt Reservoir State Recreation Area, an officially designated International Dark Sky Park.

McCook | Nebraska

You don’t realize it at the time, but in the four hours it takes to get from Omaha to McCook, you’ve gained 1,500 feet in elevation. McCook is in the High Plains, a place once suggested to be ridden of people and given back to nature and the buffalo.

That’s where the spirit of Buffalo Commons was sparked by those who love this land the most, and McCook is at the center of it. Downtown is charming, with cobblestone streets, shops, and the only Frank Lloyd Wright House built in Nebraska. Visitors can learn more about the region at the Museum of the High Plains.

McCook is a birding paradise thanks to its location on the Central Migration Flyway, where you can see dozens of birds, including those talkative sandhill cranes. Anglers love this place, too, as there are four state recreation areas nearby.

The Corn Palace-Mitchell, South Dakota
The Corn Palace | photo via fredluna8175

Hot Springs | South Dakota

For all the coolest attractions in the Black Hills, set your home base as Hot Springs. Despite all the surrounding natural beauty, the hot springs from deep below the surface have always been a lure to this region.

That includes the Cheyenne Indians and settlers who built a resort town around the health benefits of the thermal features. Much like Hot Springs, Arkansas, a bunch of bathhouses popped up in town, a stark contrast to the Wild West antics of Deadwood, just 100 miles away.

It turns out that this area was popular in prehistoric times as well. You can visit the Mammoth Site to learn more. More modern history is found at the Fall River Pioneer Center.

Other notable sites within driving distance are:

Mitchell | South Dakota

On the other side of the state, Mitchell is home to the World’s Only Corn Palace right in the heart of the historic Main Street. The best time to visit is in late August during the Corn Palace Festival or the summer when the Corn Palace Stampede Rodeo comes to town.

Explore the Dakotas of the early 20th Century at the Dakota Discovery Museum. Lake Mitchell, just north of town, offers four seasons of fun and an ancient exploration at the Prehistoric Indian Village.

Even a winter trip here is exciting, with hunting trips planned by expert guides or stay inside and play bumper boats on the ice rink. This small town also has a great food scene, with more than 50 restaurants.

Devils Lake | North Dakota

While the name doesn’t sound enticing, the story behind it sure is. The Dakota people believed the lake to be sacred, and that “spiritual” belief was interpreted as a bad spirit – and is there a worse bad spirit than the Devil?

Devil’s Lake isn’t your typical Midwestern lake. In fact, it’s more like the Great Salt Lake than anything. Without an outlet, water levels depend on rainfall and evaporation. That means the water has a high salt content and the lake’s high salinity levels contribute to the fish populations, particularly for species like walleye, northern pike, and perch.

The lake is perfect for boating or paddling and even has its own island at Grahams Island State Park. Scenic drives are spectacular, as several causeways crisscross various sections of the 190,000-acre lake.

For nightlife or a rainy day escape, check out the Spirit Lake Casino & Resort.

Medora | North Dakota

This beautiful landscape inspired a man to say, “I have always said I would not have been President had it not been for my experience in North Dakota,” is right here in Medora. That man was Theodore Roosevelt.

Medora is the gateway to the south unit of Theodore Roosevelt National Park. Enjoy the badlands landscape, scenic drives, and unique hiking trails. Explore the historical landmarks that Roosevelt loved, or channel your Wild West persona at the North Dakota Cowboy Hall of Fame.

Did you know that Medora is also a musical? Summer guests get this boot-stomping experience in an outdoor performance. Camp under the stars or stay in a chic covered wagon, then explore the trails by foot or horse during the spectacular sunrise.

Holland, Michigan
Holland, Michigan | photo via taylorledford25

Enjoy Small Towns and Big Time Fun in the Midwest

True to its name, you can also find the geographic center of the United States in the Midwest. Even if you try to question it, the United States Geological Survey is one step ahead of you.

Here’s a breakdown of the geographic centers of…

This sample of small, underrated towns in the Midwest will hopefully help spark your interest in the Heartland. While more than a dozen interstates connect these prized places, it’s the road less traveled that often brings the best surprises.