From the nonstop activity of the City That Never Sleeps to the beautiful year-round climate of the City of Angels, it’s easy to understand why travelers flock to America’s largest metropolitan areas. But what if you’re searching for a more laid-back destination — one that doesn’t welcome 20 million (or more) visitors a year?
Videos by TravelAwaits
Enter the Midwest.
With plenty of room to spread out across the tallgrass prairie and around the large lakes, “flyover country” has much more space per person than the more densely populated Northeast and South. These are 13 of my favorite Midwestern towns, along with my recommendations for the best time to visit.
Note: Size is relative. I’m using a population cap of 35,000, since that’s about half the size of the Midwestern community I currently call home.
1. Pella, Iowa
Population: 10,400
When you visit this quaint Midwestern town, you’ll feel like you’ve traveled way beyond an hour southwest of Des Moines and have magically arrived in the Netherlands. Founded by Dutch immigrants, Pella has tall brick facades, slowly spinning windmills, and clear canals reminiscent of North Holland.
To experience Pella at her peak beauty, visit in early May when the tulips are in bloom. And whenever you go, don’t leave without enjoying frikandel, frites, stamppot, or poffertjes at #DutchFix.
Pro Tip: Don’t miss these additional under-the-radar towns in Iowa.
2. Winterset, Iowa
Population: 5,300
Also in south central Iowa, Winterset was the birthplace of Western legend John Wayne and the heart of the covered bridges made famous by author Robert James Waller (as well as Clint Eastwood and Meryl Streep). While the bridges of Madison County are picturesque in every season, they’re especially beautiful in the fall, when the changing leaves accent the red bridges.
Pro Tip: Be sure to check out these 25 stops in and around Winterset.
3. Galena, Illinois
Population: 3,200
Although Illinois is called the Land of Lincoln, the town of Galena is better known as the former home of Civil War hero Ulysses S. Grant. Among the town’s well-preserved 19th-century buildings is the Italianate-style red brick home of the former president. Other historic buildings include the city’s oldest residence and the stunning Belvedere Mansion.
Many of the historic homes in Galena are only open seasonally, so it’s best to visit between May and October.
Fun Fact: More than 85 percent of the homes in Galena are listed on the National Register of Historic Places.
4. Jasper, Indiana
Population: 16,000
Roughly halfway between the towns of Santa Claus and French Lick, Jasper is in southwest Indiana. Step inside Saint Joseph Catholic Church to marvel at the mosaics and stained glass windows. Then stroll along the riverwalk, taking time to stop at the working gristmill. As a nod to the town’s large German-American community, grab some schnitzel or wurst at the Schnitzelbank Restaurant before you go!
While Jasper is definitely chilly in December, visiting during the holidays gives you the opportunity to also visit the nearby town of Santa Claus, which embraces the white-bearded Christmas character like no other.
5. Abilene, Kansas
Population: 6,300
You may already know Abilene as the home of World War II general-turned-United States president Dwight D. Eisenhower. But you also won’t want to miss the Seelye Mansion on the other side of the railroad tracks from Eisenhower’s humble farmhouse or pass up the James Beard Award-winning, family-style chicken dinners at the Brookville Hotel.
If you visit the Eisenhower Presidential Library to commemorate the anniversary of D-Day on June 6, you’ll be humbled by the chance to thank the dwindling numbers of veterans and Rosie the Riveters for their service to our country. And if you find yourself in Abilene during the winter holidays, you’ll love the decorated Victorians along South Buckeye Avenue and the hundreds of poinsettias that fill the Seelye Mansion.
6. Holland, Michigan
Population: 35,000
If you didn’t get enough of a Dutch fix in Pella, then head east to Michigan. In the Windmill Island Gardens of Holland, the DeZwaan windmill is surrounded by 36 acres of canals, flowers, and greenery that look like a smaller-scale Midwestern version of Keukenhof. Located on the east bank of Lake Michigan, Holland is also home to the Big Red Lighthouse, several parks, and blueberry farms.
Enjoy the tulips in bloom in late April and early May, or visit in the warmer summer months, when the blueberries are at their peak.
Fun Fact: The DeZwaan windmill in Holland is the only authentic Dutch windmill operating in the U.S.
7. Inver Grove Heights, Minnesota
Population: 35,000
Although it’s on the outskirts of the Twin Cities metropolitan area, this town feels much farther from the hustle and bustle of Minneapolis and Saint Paul. Hugging the left bank of the Mississippi River, Inver Grove Heights offers miles and miles of trails. One of the coolest experiences is the Rock Island Swing Bridge. Built in 1894, this double-decker bridge once crossed the river into Newport. Today, the pedestrian-only bridge juts halfway over the water, providing uniquely scenic views.
And if you’re a football fan, Inver Grove Heights is just down the road from the Minnesota Vikings training center. I recommend visiting the town in the summer months, since the Vikings typically practice in July.
8. Parkville, Missouri
Population: 7,000
Recognized as having the most charming main street in Missouri by USA Today, Parkville is sandwiched between a bend in the Missouri River and a nature sanctuary. Stroll between the waterfront and the walking trails, search for vintage finds in the antique shops, sip a latte, or say oui to a meal at Cafe des Amis. I recommend visiting in the late spring or early fall.
9. Ashland, Nebraska
Population: 2,600
Roughly halfway between Omaha and Lincoln, Ashland’s two biggest attractions connect the heavens and the earth. Explore one of the largest collections of Cold War aircraft, missiles, and more at the Strategic Air Command & Aerospace Museum. Then go on a Cornhusker-style safari by driving past antelope, deer, and bison at the Lee G. Simmons Conservation Park. Don’t leave Ashland without digging into a steak at Round the Bend.
Visiting Ashland in the late spring or early summer increases your chances of spotting fawns and bison calves at the park.
10. Jamestown, North Dakota
Population: 15,500
If thinking about the tallgrass prairie states that stretch from North Dakota to Texas gives you flashbacks to Dances with Wolves, then Jamestown will bring your visions to life. Located about 100 miles directly west of Fargo, this quaint Midwestern town is home to the National Buffalo Museum. (You’ll know you’re in the right place when you spot the 26-foot-tall bison statue.)
While some portions of the Midwest can be hot and muggy in the summer, Jamestown’s location just 150 miles from the Canadian border makes it a great destination during the hottest summer months.
11. Geneva-On-The-Lake, Ohio
Population: 1,200
About an hour up the coast of Lake Erie from Columbus, Geneva-on-the-Lake is the Buckeye State’s original summer resort town. The best time to visit is when you can take full advantage of the lakeside location by swimming in and boating on the lake — between Memorial Day and Labor Day weekends.
When hunger strikes, head over to Eddie’s Grill. This ’50s-style eatery has been serving up American classics like steakburgers and shakes since before McDonald’s was founded.
12. Mitchell, South Dakota
Population: 16,000
This town is best known for its palatial building decorated with elaborate agriculture-inspired murals fashioned out of corn and other natural materials. After you’ve explored the one-of-a-kind Corn Palace, grab a bite at The Depot. This former train station now serves up pub fare in a unique historical setting. Cap off your visit with a movie at the Starlite Drive-In.
The best time to visit Mitchell is when the new murals are completed each year, typically in the fall.
Pro Tip: Here are eight other things to do in Mitchell.
13. Cedarburg, Wisconsin
Population: 11,500
About 20 miles north of Milwaukee, the town of Cedarburg has a winery, brewery, and distillery sure to wet any whistle. Housed in a former wool mill, the Cedar Creek Winery produces a wide variety of wines from grapes grown in Washington, New York, and Wisconsin. Just down the road, in an equally historic mill, Rebellion Brewing brews ambers, ales, IPAs, and lagers. If spirits are more your style, then check out the bourbon and gin at the Handen Distillery.
And don’t leave this idyllic farmland region without a meal at Farmstead. It’s wildly popular with the locals, so be sure to make reservations or stop by outside of peak hours, or else be prepared for a wait.
My favorite time to visit Cedarburg is in October, when the fall colors are in full swing.
Pro Tip: If you visit Wisconsin on a weekend, you may notice that Fridays are all about fish fries (even for non-Catholics and even outside of the Lenten season). Here’s the fascinating story behind the century-old, statewide tradition.
