Oconomowoc Lake, WI

Tucked into southeastern Wisconsin’s Lake Country, the Village of Oconomowoc Lake is a quiet community wrapped entirely around the shoreline. Its roots go back to the mid-1800s, when rail lines made the area a favorite summer retreat for families traveling up from Milwaukee and Chicago. Today, that history is still visible in the grand lakeside estates, lush tree canopy, and peaceful private roads that give the village its secluded feel.

ATTRAwkwafaba / CC BY-SA 4.0

Because the village itself is almost entirely residential, residents head right next door to the neighboring city of Oconomowoc for daily essentials, charming downtown dining, local shops, and healthcare. Families are served by the well-regarded Oconomowoc Area School District, while commuters have an easy drive along Highway 16 and I-94 to both Milwaukee and Madison. From sunny summer afternoons spent boating and sailing to quiet winter mornings on the water, it offers classic Wisconsin lake living at its most relaxed.