Well being from that area I guess I am a little bias. Monroe, Juneau, Adams, Wood & Sauk Counties are amazing, no it's not Up North but you can/will appreciate that it's not. Black River Falls is beautiful, you can do a day trip from Castle Rock Lake just north of the Dells to BRF and stay in BRF over night and come back, it's a little over 200 miles round trip. BRF is about an hour by car from where I live one of these days we are planning to trailer to BRF drop there and go as North as possible in a day and spend the night and come back.
Yes, there are fields, there are also old railroad bed as trails, if the weather and snow is right you could also ride to Lacrosse.
There are really no direct trails out of Downtown Dells, but if there are plenty of trails, homes for rent in that area.