Lake Geneva: Victorian Shore Path, Yerkes Observatory & Winery Weekend

Lake Geneva has been Chicago's premier lakeside escape since the 1870s, when wealthy families built Victorian estates along Geneva Lake's shores. A Wisconsin right-of-way law requires public access along the entire 21-mile shoreline, and the Geneva Lake Shore Path — one of the oldest continuously used footpaths in Wisconsin — passes directly in front of those grand estates. Yerkes Observatory in Williams Bay houses the world's largest refracting telescope: a 40-inch lens installed in 1897 that the University of Chicago operated as an active research facility until 2018 and now opens for guided public tours. Staller Estate Winery rounds out day one; Abbey Springs' lakefront marina and walking trails close the weekend before the 90-minute drive home.