Trek,
Where in Wisconsin is your sister going to be teaching? I live in Iowa, but right on the border with Wis. and do quite a bit of my riding across the river. It is a beautiful area to ride in. Hills and valleys, tons of quiet county roads.
The area around Madison is great for biking, too. Madison is often rated one of the best biking cities in the county. Active bike clubs, many rides and riders and all different types of terrain.
Northern Wisconsin also has some wonderful biking. I'm talking road riding here, but Wis. also has some great off-road trails.
As for time of year, it gets REAL cold in the winter. Fall is gorgeous, with the trees changing colors. Summer can be hot and humid, but you never know.......it's very unpredictable. Spring is usually cool and a bit wet. So pick the weather you like.
If there's any other questions I can answer, I'd be glad to. Just post...........
annie
Time is a companion that goes with us on a journey. It reminds us to cherish each moment, because it will never come again. What we leave behind is not as important as how we have lived." Captain Jean Luc Picard