If you have the time to visit only one other city, look no further. Madison - home to Josh's alma mater, University of Wisconsin-Madison - is the state capitol, situated on an isthmus between Lake Mendota and Lake Monona. Take the journey an hour west of Oconomowoc and enjoy beers on the Union Terrace on campus, visit the Capitol Square farmer's market (Stella's cheesy bread is a must), and take in the sights and sounds of campus as Welcome Week 2022 commences.
Lake Geneva is small paradise just an hour south of Oconomowoc. Enjoy good food, walks around the lake, boutique inns, and lots of shopping.
Late summer/early fall is the perfect time to explore Wisconsin's largest metropolitan area. Breweries aplenty, miles of Lake Michigan lakeshore access, golfing, food in the historic Third Ward, and more will keep you busy.