5 Delightful Midwest Towns

History & Heritage, Magazine Features

Experience big-city activities without abandoning small-town comfort

Some of America’s most relaxing small towns and hamlets are comfortably tucked into the Midwest. Big cities and coastal tourist hubs are nice but also hectic. Vacations are first and foremost about relaxing, and for relaxation, these friendly towns cannot be beat.

Saugatuck, Michigan


Visitors to Saugatuck can peruse art galleries and take a lazy cruise down the Kalamazoo River.

Resort towns either lean more rural or urban, but in Saugatuck natural and man made attractions exist in perfect symbiosis. A good example is Mount Baldhead. While the 600-foot high sand dune is an incredible feat of nature, a small abandoned Cold War radio tower with a large white ball on top gives the dune its character and namesake.

The 300-step climb to reach the top of Mount Baldhead might be difficult for some, but it’s worth it for the view from the area’s highest point. To get down, you can either take a scenic stroll through the majestic forest that keeps Mount Baldhead from blowing away or madly dash directly down the dune’s side. Either way, continue on to find Oval Beach and its beautiful view of Lake Michigan.

There are plenty of manmade wonders to experience in Saugatuck as well, such as the majesty of coffee. Make sure to start the day at Uncommon Coffee Roasters, which imports beans from over a half-a-dozen countries, including Guatemala, Honduras and Ethiopia. In order to assure fair treatment, Uncommon buys directly from small farms in these regions, visiting them whenever possible. This ensures guilt-free coffee with gourmet taste.

Once you’re good and caffeinated, discover why Saugatuck is called the “Art Coast of Michigan.” It is impossible to walk from one street to another without discovering a piece of public art or a gallery. The best work usually resides at the Saugatuck Center for the Arts. The center features its own theater company, a variety of film festivals, and a gallery showcasing the best of both local and visiting artists.

Madison, Indiana

Due to its location on the Ohio River in southeastern Indiana, Madison was a thriving port back in the 1800s. When the railroad rendered river trading obsolete, Madison fiercely stuck to its roots. In time, this led to what the Chicago Tribune calls the “best preserved town in the Midwest.” Madison continually earns the title though preserving its culture and nature. History buffs can see Civil War lore on display at the Jefferson County Historical Museum. Nature lovers can hike along one of Clifty Falls
State Park’s scenic trails or drive half an hour for horseback riding at Shilo Farms.

However, the unassuming town hides a dark secret. Madison is also known for preserving the spirits of the dead. Locals tell tales of an unseen woman crying for help at the Historic Broadway Hotel and Tavern, strange floating lights at the Ohio Theater and deceased inmates never released from Old County Jail. Brave visitors should consider the “Ghosts of Madison” tour, the haunted river walk and the haunted pub crawl.

Stillwater, Minnesota



There are many great perspectives from which to view Stillwater. While exploring terra firma, it is best visit one of Stillwater’s beautiful parks, the most unique being Teddy Bear Park. The park’s namesake comes from its numerous cuddly teddy bear statues as large as, and sometimes larger than, people. The figures warm the heart of kids and adults alike. After the park, visit some of Stillwater’s over 100 independently owned stores. Not the least of which is Nelson’s Ice Cream. Daily Meal calls the 95-year-old shop one of the world’s 25 best ice cream stores. True ice cream fanatics should attempt the five-scoop Lumberjack Challenge and become immortalized in Nelson’s Hall of Fame.

Afterwards, take to the water and experience the St. Croix River, perfect for any kind of aquatic experience. Adventure-seekers can tour up and down the river with a kayak or let loose with a speedboat. Those looking for a more relaxing or romantic venture can leisurely cruise on a paddlewheel boat or a personal gondola.

Travelers can even sail through the air on a hot air balloon ride with Stillwater Balloons. Experience Stillwater’s glimmering bodies of water and forests from a perspective usually reserved for birds. Flyers might even see sights in the Twin Cities, about 20 miles away. Every flight comes to a close with a champagne toast on landing.

St. Genevieve, Missouri

As Missouri’s oldest settlement, St. Genevieve is a city of stories. The town’s welcome center provides a quick glance at St. Genevieve’s history. Travelers can also visit the Bolduc House Museum to hear more
stories about what St. Genevieve was like under Native American, French, Spanish and American rule. To touch a piece of that history, visit the Anvil Saloon. In 1855 a steamboat got stuck on a sandbar in the Mississippi River. Desperate to lose weight, the crew unloaded a huge piece of carved maple. To
this day that piece of maple has served as the bar for the Anvil Saloon, one of the town’s best places to dine.

While St. Genevieve has no shortage of fascinating historical tales, some of the area’s most interesting stories come from Izzy, Thor and Gracie: the tigers from Crown Ridge Tiger Sanctuary outside of town. The sanctuary is a rescue facility for tigers previously kept in horrible conditions. Instead of breeding the tigers or exploiting them for profit, Crown Ridge’s mission is the fair treatment of big cats. A variety of tours allow people to meet and possibly even feed Izzy, Thor and Gracie.

Cedarburg, Wisconsin



One place where the word “festive” is completely appropriate is Cedarburg, thanks to its huge lineup of festivals. The Winter Festival, held the third full weekend of February, features outdoor music, hayrides and ice sculpture contests. If it’s getting too nippy out, beer tasting, a chili contest and the hearty pancake breakfast are sure to warm you up.

In the fall, Cedarburg has its own Oktoberfest, held the second full weekend of October. Like all good Oktoberfest celebrations, it is not just an excuse to drink beer but also a celebration of German
culture. Oktoberfest features everything from German food and music to a best lederhosen contest.

Cedarburg’s spring festival, Cedarbrew, showcases the best of the town’s restaurants and distilleries. It’s a great way to support local businesses and fill your stomach at the same time. Cedarbrew is held the second Friday of April.

Every summer during the last full weekend of June, 100,000 visitors come to Cedarburg’s Strawberry Festival. Chow down on every kind of food that pairs with strawberries, be it classics like strawberry shortcake or a surprise like strawberry brats. Once you’ve had your fill of strawberries, indulge in the music, shopping and artist showcase. Or visit year-round attractions like Wayne’s Drive In, a 1950s-style diner and rollerblading rink; or award-winning Cedar Creek Winery.

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