8 Cutest Small Towns in the Midwest

Easy railroad access from Chicago to Lake Geneva made this small lakefront town popular with Chicagoans who were wealthy enough to pepper the place with Gilded Age mansions. Today, some of the mansions have been turned into museums and hotels. There's a small urban winery for tastings, a spa scene, and antique shops, but the real draw here is Lake Geneva itself. The 21-mile Shore Path wraps around the lake for hiking and a vintage-inspired cruise ship allows passengers to get out on the water. 

Over on Lake Michigan, Traverse City is highly celebrated for its yearly National Cherry Festival, Traverse City Film Festival (co-founded by Michael Moore), and access to the Sleeping Bear Dunes, a gorgeous 64-mile stretch of sandy beaches, coves, and hills along the shores of Lake Michigan. Downtown Traverse City is often pointed to as an example of city restoration, and the area teems with boutiques and coffee shops. At night, there's a fun bar scene on Front and Union streets. Exploring on foot or by bike is highly recommended. 

Lake of the Ozarks was created during the Depression when the construction of Bagnell Dam allowed for 55,000 acres of lake. The town itself centers around boats and boating activities. Many visitors rent a houseboat (or at least a pontoon) and spend their time fishing, swimming, paddling, and soaking in the natural beauty. On weekends, thousands of boats head for Grand Glaize Bridge where an epic boat party takes place from noon until sunset. Expect heavy drinking, nudity, water balloons, and loud music. Luckily, if the party isn't your scene, there's plenty of lake to go around. 

With just over 300 residents, Keystone in the Black Hills of South Dakota is truly a microtown. It was originally built as a gold mining town, but after tourists started to arrive to see the Mount Rushmore monument (two miles away), the population decided there was more money in tourism. Many of the attractions pay homage to the unique history and interesting heritage of Keystone. Rushmore Cave, a natural attraction that's an estimated 60 million years old, offers a guided tour through underground passageways and enormous caverns flanked with stalactite and stalagmite formations. The 1880 Train takes passengers on a two-hour journey on a vintage steam train through the picturesque Black Hills. Visitors can also stay at Custer State Park, which has four lodges and several campground sites. 

Mackinac Island (pronounced Mackinaw) was once home to Native Americans, French fur trappers, and Catholic Jesuits who reached the island by paddling canoes between Michigan's upper and lower peninsulas that connect Lake Huron to Lake Michigan. Today, Shepler's Mackinac Island Ferry brings hordes of summer tourists to the 3.8-square-mile island, where life moves at a slower pace. Much of the island is protected state forest, but the historic downtown features a variety of restaurants, art galleries, and world-famous fudge shops. Horse-drawn carriages and bikes are the best way to get around, as cars aren't allowed. 

Teeny-tiny Custer (with population of around 2,000) makes a cute home base for both history and adventure lovers. It's one of the oldest towns established by European Americans in the Black Hills of South Dakota and is near the infamous site of The Battle of the Little Bighorn, also called Custer's Last Stand, the most decisive Native American victory in the Plains Indian War. Most visitors pay homage to the not-yet-finished Crazy Horse Memorial (which will stand over 500 feet tall when it's finally carved out of the mountain) and visit Custer State Park, home to over 1,300 buffalo. For bikers, the George S. Mickelson Trail is a 109-mile rails-to-trails facility for biking. 

Some Wisconsin residents refer to Wisconsin Dells as the Disney World of the Midwest, and if you've survived one of the region's brutal winters, the annual opening of Noah's Ark Water Park might feel just as spectacular as a trip to Orlando. The destination has been drawing vacationers from around the world for over 150 years. It has more water parks (both indoors and outdoors) per capita than any other place in the world as well as access to the natural Wisconsin Dells, a beautiful gorge with rock formations. The main strip is lined with charming boutiques, home good shops, old-fashioned general stores, and fudge and ice cream parlors. 

Kohler is a cute village on the Sheboygan River that's well-known for being home to the Kohler Company, one of the world's leading high-end plumbing suppliers. The Shops at Woodlake provide upscale retail therapy, plus the village is home to two professional golf courses: Whistling Straits and Blackwolf Run. Winery visits, cooking classes, and yoga by the lake are other popular activities in the area. The American Club, which offers several gourmet restaurants and an excellent spa, is easily one of the most luxurious hotels in Wisconsin. 

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