Six Small Towns That Are the Definition of Charming

Elkhart Lake: Stylish, Relaxed
This quaint lakeside village veritably oozes charm. There are white clapboard resorts with porches and cupolas, sandy beaches, tiki bars, and a pretty brick promenade, all positioned to take best advantage of the Mediterranean-like blue waters.
According to Kathleen Eickhoff, executive director of Elkhart Lake Tourism, “business owners here are front and center.” In fact, it’s not unusual for guests of The Osthoff Resort, Siebken’s (which turned 100 this year) and Victorian Village to pop in to say hello to the owners upon arrival.
Adding to the charm is that nearly everything is walkable. Stroll in one direction and you’ll find yourself at Two Fish Gallery. In the other direction, Gina’s for high-end outdoor apparel and home décor items. And smack dab in the middle is Vintage, a wine store with tasting room. Bikes are a common sight too, with serious pedaling in the Kettle Moraine a major draw. Racing at Road America is the modern iteration of the road racing once staged through the streets of the village.
Most Unexpected: Hands down, the culinary scene. Start at Off the Rail for coffee drinks and breakfast goodies, Lake Street Café for lunch, Gesserts for ice cream, Paddock Club or Lola’s for fine dining, and Brown Baer for drinks and live music. The cooking school at the Osthoff is a culinary treat too.
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