Top Small Towns in the Midwest

The Midwest is a region that really has it all in terms of landscapes, from the gorgeous Great Lakes to striking sand dunes, densely wooded forests, and beyond. The bucolic, wide-open spaces and dynamic cities of America’s heartland are ripe for exploration, as more visitors focus on previously overlooked domestic destinations.

Petoskey, Michigan

This cute waterfront town sits near the “Tip of the Mitt” in the northern reaches of Michigan’s Lower Peninsula. Enjoy the historic downtown, where you’ll find artisanal preserves gem American Spoon, former Hemingway haunt Stafford’s Perry Hotel, and upscale kitchen and bar, Pour. Outdoor activities are also key in the area, as it’s home to the world-class Bay Harbor Golf Club as well as great hiking along the North Country Trail and in the Bear River Valley Recreation Area. Don’t forget to hunt for the famous Petoskey stones at nearby Petoskey State Park. Wine enthusiasts should visit some of the designated wineries along the region’s wine trail, such as Walloon Lake Winery (a well-known lake where Hemingway’s summer cottage was located) and Pond Hill Farm, part of the Tunnel of Trees drive.

Hill City, South Dakota

Hill City’s population totals just under 900, but this small South Dakota town packs a big punch. A few of its can’t-miss sites include Prairie Berry Winery and Miner Brewing Co. for locally crafted and sourced beverages, the 1880 Train for a two-hour, narrated round-trip journey between Hill City and Keystone, and the family-friendly Palmer Gulch Campground, which holds a number of rodeos over the summer. Hill City is also within driving distance of major South Dakota draws like Custer State Park, Mount Rushmore National Memorial, and Crazy Horse Memorial. The town even makes a lovely jumping off point for checking out two of the state’s best national parks, Wind Cave (about 30 miles away) and Badlands (about 90 miles away).

Kohler, Wisconsin

Located in the heart of the Midwest in Wisconsin, the village of Kohler was one of the nation’s first planned communities — the green spaces here were actually designed by the same landscape architect who created Central Park. However, the crown jewel of Kohler is undoubtedly The American Club, an elegant hotel with Wisconsin’s only AAA Five-Diamond rating. Spend some time relaxing at the Waters Spa or hitting the links at the Whistling Straits or Blackwolf Run golf courses. Kohler is conveniently located about 55 miles from Milwaukee and 145 miles from Chicago, so it’s accessible even to travelers outside the region.

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