The Midwest's Greatest Towns

The Greatest Towns contest began in early 2016 with simple rules: nominate your favorite town (population under 100,000) known for great scenery, arts, food and attractions. We picked a finalist from each state, and you voted online. After a mighty challenge from Decorah, Iowa, the title went to Traverse City. But the ultimate winner? You, whenever you get a few days in any of the 12 nominated towns. Click or tap ahead to meet them all.

Slip your paddleboard into the Boardman River’s slow current south of Traverse City, and you’ll quickly understand this northern Michigan town’s tendency to drive other towns a little crazy.

The Boardman—a narrow, clear stream where ducks skitter ahead of you and trout glint beneath you—carves a lazy C through the heart of the city of 15,000. Tucked somewhere in the buildings up the bank are six breweries visited by Paddle for Pints kayak tours that sold out their 2016 dates by early April. At Lay Park, where you’ll lift your board around a dam, boardwalks and the river form a front porch for townhomes. As the river straightens for its run to Lake Michigan, you’ll look up at balconies filled with diners savoring views of both the river and the lake. Working your way through all the restaurants you pass could fill a steady week of high-end dining.

One of the walls beside you backs the State Theatre, home to the famed Traverse City Film Festival (held each July) and the place to catch 25-cent classics and kids’ movies on many mornings. Across the street from that is the City Opera House, where nationally known authors appear several times each year to discuss their works, like Gone Girl and Friday Night Lights.

Finally, waves slapping your board signal the passage into Grand Traverse Bay’s West Arm, which is bracketed by the Old Mission and Leelanau peninsulas, each loaded with orchards and wineries. On the Leelanau’s far edge, the towering sands of Sleeping Bear Dunes National Lakeshore reveal hundred-mile lake views.

Considering that any one thing on this afternoon itinerary would be a draw in most small towns, you can see where others might think Traverse City lays it on a little thick. (Did we mention July’s National Cherry Festival that draws 500,000 people?) But to emerge as  the Midwest’s Greatest Town, only the A game will do.

Essential Day-Trips

1/ Leland’s Fishtown You’ll feel like you’re on a movie set among the weathered shanties and smokehouses from the early 1900s. Boutiques and galleries now fill many of the buildings.

2/ Leelanau Wine Trail Three driving-tour loops lead to 26 wineries  throughout a surprising mix of microclimates, producing a diverse  tasting tour.

3/ Power Island Load up on local eats at Burritt’s Fresh Markets, rent a boat, and motor 6½ miles to the nature preserve in the West Arm of Grand Traverse Bay.

Midwest Living's Traverse Area Trip Guide

The University of Kansas headlines this town 40 minutes west of Kansas City, delivering all the expected town-and-gown essentials, such as performing arts, a lawn-dotted campus and Rock Chalk sporting events. But along downtown’s Mass Street, things skew into a bit of an inland Portlandia. Mass Street Soda hosts craft root beer tastings. Free State Brewing was doing craft beer before everyone thought it was cool. Cats lounge in shops selling used vinyl (Love Garden Sounds) and used books (The Dusty Bookshelf). Sunflower Outdoor and Bike Shop promotes prep seminars for an off-road race called the Dirty Kanza 200. And if something can be decorated, locals really, really love to put a bird on it—provided it’s a Jayhawk. 

Midwest Living's Lawrence Trip Guide

If throwback country acts and down-home comedy are your jam, Branson’s famous theaters still have you covered. But southern Missouri’s longtime vacation mecca has seriously broadened its range in recent years, offering a great week even if you still don’t get Yakov Smirnoff.

1 Table Rock Lake  Countless coves along 800 miles of wooded shoreline provide endless options to water-ski, fish, swim, or anchor the pontoon and bob in the sun.

2 Golf Creeks and limestone cliffs dot local courses. The stars: Branson Hills (named best in the state) and a couple of calendar-worthy layouts at Big Cedar Lodge.

3 Big Cedar Lodge Bass Pro Shops owner Johnny Morris overlooked no detail in creating this luxury resort with boating on Table Rock Lake, horseback riding and a top-notch spa.

4 Trails Look for Branson to emerge soon as a hiking/trail-running destination. Streams trickling down rocky walls seem to mark every Instagrammable mile. 

5 Ziplines The treetop craze has arrived here in full force. One of our favorites is Branson Ziplines, where the rope bridges may be more thrilling than the zipping.

Midwest Living's Branson Trip Guide

The obvious question after a few minutes in Columbus:  How did this happen?  How is a town of 45,000 people packed with buildings and art created by designers known even by people who know nothing about design? Names like I.M. Pei and Dale Chihuly left their mark here, earning Columbus recognition from the American Institute of Architects as America’s sixth best city for architectural innovation.

How?! Answer: J. Irwin Miller. In the 1950s, the local Cummins Engine Company executive determined to draw world-class workers to Columbus by elevating the entire town’s attitude via design. He subsidized public buildings, as long as a renowned architect designed them.  After a narrated bus tour around town, you may get so inspired that you start wondering whether Cummins is still hiring. But if you’re just passing through, stay at Hotel Indigo, with a sleek design echoing the town’s aesthetic and a location within walking distance of many signature attractions. 

Midwest Living's Columbus Trip Guide

It doesn’t take long to spot Norwegian roots in northeast Iowa. There’s Luther College (go Norse!), the Vesterheim Norwegian-American Museum and a Nordic Fest in July. All that Scandinavian tidiness (along with the wooded hills and cool streams) makes this one of our go-to picnic spots, thanks to Decorah’s renowned pizza, beer and parks along the Upper Iowa River. The local recipe for success:

• A six-pack of King Sue Double IPA from Toppling Goliath, voted one of the top 50 beers in the world by website RateBeer for its hoppy citrus explosion.

• A Chicken Cordon Bleu pizza from Mabe’s, a 63-year-old staple with chewy, thin-crust pies that have drawn national attention.

• A picnic table at Dunnings Spring Park, where lush foliage surrounds a waterfall that works its way down a 200-foot-tall cliff face.

Tip: Pack a fly rod. Decorah=trout streams. Really.

Midwest Living's Decorah Trip Guide

200 specialty shops on Main Street. All of the shopping. None of the mall.  That’s one key attraction in this northwest Illinois town of 3,400 founded in 1826 and now known as one of the country’s great antiquing destinations.  Here are a few more:

• 31 B&Bs located in town

• 10 golf courses in the county

• 85 percent of Galena’s buildings are on the National Register of Historic Places

Midwest Living's Galena Trip Guide

“Rapid” recently found its voice and emerged from its role as middle child between the Black Hills and Badlands. Give it a day or two during your road trip to Mount Rushmore. For a solid downtown sampler, hit these stops:  

Shop Prairie Edge’s intriguing inventory of Native American art, books and music makes it as much cultural museum as retail store.

Drink Atop the Hotel Alex Johnson, Vertex Sky Bar (open to hotel guests and club members) mixes classics and inventive cocktails. The patio (complete with a fireplace) overlooks the city and neighboring Black Hills.

Listen Summer Thursday nights bring outdoor concerts to Main Street Square and the Summer Nights stage, both in the heart of town. With two different types of music scheduled each week, you’ll definitely find tunes to fit your taste.

Eat Kol illustrates Rapid City’s newly expanded taste in cuisine and cocktails. In a sleek dining room anchored by a long, curving bar, a coal-fired oven produces crispy pizzas laden with the likes of eggs and Gouda.

Midwest Living's Rapid City Trip Guide 

No Midwest town nails the NPR/adventure intersection like the classy village on Lake Superior’s shore. The weekend essentials: 

GoPro When you paddle a kayak into the  caves of the Apostle Islands National  Lakeshore, you’ll want footage.

Bikes Roll off the Madeline Island ferry, grab a burger (with a side of civil disobedience) at Tom’s Burned Down Cafe, and pedal to Big Bay State Park across the island.

Berry pail U-pick farms surround Wisconsin’s self-described Berry Capital, providing a good start on a picnic lunch.

Big Top Chautauqua tickets Summer shows at the circus tent in a  meadow include big names like Lyle Lovett and the Nitty Gritty Dirt Band.

A little black dress The five-course dinner at the Old Rittenhouse Inn perfectly caps a day on the water or trail.  

Midwest Living's Bayfield Trip Guide

This cowboy-centric hamlet literally tucks into the shadow of western North Dakota’s badlands. But Medora’s biggest point of pride is how Teddy Roosevelt credited his presidency to his time here as a rancher. Plan your own brush with greatness during a one-day tour.

8 a.m. / Breakfast at the Cowboy Cafe Old photos of genuine old cowhands cover the cinder-block walls. Order bacon and coffee, and feel as close as you ever will to living in a George Strait song.

10 a.m. / Mountain biking the Maah Daah Hey Trail Dakota Cyclery tailors badlands rides to your skill. Even if you cover only a few miles of this 120-mile legend, it’ll feel epic.

Noon / Tour Theodore Roosevelt National Park  A paved road reveals panoramas of the Little Missouri River and 20-yard encounters with bison.

3 p.m. / TR Impersonator Show Joe Wiegand’s spirited act will have you firming up your handshake and shouting “Bully!” for the rest of the day.

5:30 p.m. / Pitchfork Fondue It’s practically a state law that visitors join this signature meal featuring steaks dunked in boiling oil.

7:30 p.m. / Medora Musical Teddy, the West and unbridled patriotism get the Broadway treatment at this long-running show in an amphitheater overlooking the badlands.

Midwest Living's Medora Area Trip Guide

It’s hard to think of a state with a bigger interest in creating shade than Nebraska. And with that in mind, it makes perfect sense that Arbor Day began in this town positioned where the Missouri River valley gives way to the vast Great Plains. J. Sterling Morton launched the holiday here in 1874, and his Arbor Lodge mansion still hosts tours of both the home and its parklike setting. Next door, Tree Adventure sends visitors into a series of interconnected  tree houses and teaches lessons about conservation. Across the valley, the modern Lied Lodge features 140 hotel rooms, a massive indoor pool and the high-end Timber Room restaurant. Thousands come to town for the AppleJack Festival in September. The next month brings prime time for views of the river valley from the Missouri River Basin Lewis and Clark Center on a bluff just outside of town.

Did you know? Nebraskans planted more than 1,000,000 trees on the first  Arbor Day.

Midwest Living's Overnight Getaway in Nebraska City

Mild or wild? This village on South Bass Island plays it both ways in the Lake Erie waters near Sandusky (binge-riding destination of choice for roller coaster fans headed to the famed Cedar Point).

Mild  Rent a golf cart and putter around the island to stops like Put-in-Bay Winery; Perry’s Cave; Adventure Bay Amusement Center; a tower honoring Commodore Perry’s victory over the British navy in 1812; and numerous beaches perfect for kayaking and cruising on personal watercraft. Charter boats hook into some of the world’s best walleye fishing. And on summer Sundays, kids catch candy thrown during parades of antique cars.

Wild  Then there’s the “Key West of the Great Lakes” side of Put-in-Bay’s personality. Day-trippers pour in off the ferry, hit Main Street’s bars and test the outer limits of the golf carts’ liability waivers. There’s no better place within the Detroit-Toledo-Cleveland triangle to release your inner Parrothead. And if the bass seems a little too loud, there are always beaches on the other side of the island.

Midwest Living's Lake Erie Shore Trip Guide

The gateway to Minnesota’s rugged North Shore, Duluth (153 miles north of Minneapolis) draws visitors with roughneck charm, clapboard buildings on a rocky coastline and gulls crying over Lake Superior. Busy Canal Park packs in dozens of restaurants, shops and museums, plus arm’s length views of cargo ships passing under the Aerial Lift Bridge. Or leave the park for quieter delights: bird-of-prey sightings from Hawk Ridge, smoked-salmon eggs Benedict at Duluth Grill and heady brews at Fitger’s.

Midwest Living's Trip Guide to Duluth and the North Shore