5 Cozy Midwestern Towns You’ll Fall in Love With


2. Bayfield, Wisconsin

While Ely natives enjoy the Boundary Waters as their backyard playground, residents of Bayfield gaze upon the yawning waters of Lake Superior–biggest and surliest of the Great Lakes–from their doorsteps. Just offshore are the magical Apostle Islands, centerpiece of the Apostle Islands National Lakeshore; this mostly wild archipelago boasts historic lighthouses, magnificent shoreline cliffs, and beautiful, bear-roamed woods, as well as the charming shops and pastoral lanes of Madeleine Island just across the water from Bayfield.


But–back to the mainland. Bayfield has only about 500 permanent residents, but its ranks swell in the summer tourist season. It’s no surprise visitors from near and far make regular pilgrimages to the hamlet, which proudly calls itself “the best little town in the Midwest.” While strolling the quaint streets, you’ll find yourself dipping into bakeries, cafes, and candy shops–as if you’ve transported yourself to some timeless dream refuge of small-town America. Berry farms and apple orchards–made fertile and productive by the cool lakeshore microclimate–beckon for afternoon touring. There’s plenty of homegrown culture, too: An area institution is the Big Top Chautauqua, a grand tent-show venue on nearby Mt. Ashwabay that’s hosted everybody from Ramblin’ Jack Elliott to Nanci Griffith.

Bayfield’s also renowned for its Apple Festival, an annual October carnival of music, parades, and plenty of harvest-time delectables that draws 50,000 devotees a year.