It's often difficult to know exactly when to drive somewhere to see the changing fall colors, but when you plan to make a day of it, it's good to know what is going on from somebody local. Travel Wisconsin posts a Fall Color Report that includes the percentage of foliage that has peaked. You can look at a county and see by the color, whether it has pretty foliage. If you know a county is peaking, then you can look for large wooded areas and lakes within that county for the prettiest views. Sometimes users will post photos along with reports and you can see where they went to take the photo. It's an interactive map.
There are three especially scenic drives I would recommend. It says peak color will be during the 2nd week of October, so if you can do it then, you'll likely be rewarded with some great views. I've done them in the past, so the photos you will see are not from this year.
The first is always an annual trek for us. Holy Hill. It is a beautiful Catholic Church set atop a hill in the Kettle Moraine. You can hike the Ice Age Trail here if you're up to the challenge. Click on the link given and you will find a downloadable map you can take with you. Though there will probably be many other hikers, it's always a good idea to let someone know you're doing the hike, just in case you get lost. Sometimes I go off on a weekday on my own and forget to do that...then realize there is no cell phone coverage in this area. You can also pick up apples while you are there. Check out Pine Hill Orchard or Rim's Edge Orchard. Years ago there was a helicopter ride given by the apple stand on the way to Holy Hill, but it didn't last very long. People who lived there didn't appreciate the noise of a helicopter overhead. Now you get the best views by climbing the tower at the basilica. Good luck!
The Kettle Moraine Scenic Drive has been listed in books as one of the most scenic drives in America, and rightfully so. There's a diversity of trees, rolling hills, and a few opportunities to climb towers to see what's below you. Allow several hours to do this and expect there to be traffic. You can always stop along the way and take a short hike. Depending on how much of the drive you do, you'll have opportunities to climb at Lapham Peak or Parnell Towers. This is a good way to stretch your legs and once you're at the top, you can see for miles on a clear day.
The third is Old World Wisconsin. I have yet to visit during fall, but it's on my list for this year. This is a beautiful natural setting any time of year, and it's even more fun for families because of the historical buildings and costumed volunteers. It's only open Thursday -Sunday during October and there is an admission charge. I'd advise you check out the website before you go to see what events are happening. They do run a shuttle between villages and the parking lot, but you can choose to walk. If you do this, you might consider dressing in layers and wearing some comfortable shoes.
I'll throw in a few more, though they are a bit farther away and I've written them on my other blog which is more of a travel blog.
A few years ago we drove to Columbia County to see the Amish homesteads. If this is your thing, you'll enjoy seeing shops, buggies, and beautiful gardens at the general store. Go early in the day so you can get fresh bakery. You can download a map of the Amish businesses and places of interest at the Columbia County Visitor Bureau.
If you haven't seen the cranberry bogs up near Wisconsin Rapids, it's a beautiful destination, though we stayed overnight so we could do the tours of the fields. I learned so much and thoroughly enjoyed the student run tour Splash of Red at Pittsville. The best place for information about the whole cranberry experience is the Cranberry Growers Association website. The season runs through most of October, but if you combine a tour with the fall colors in mid month, it's even better for photography. Make time to drive the Cranberry Highway and you might see fall color, cranberry fields, and migrating birds too.
Drive to Sauk County to see the rolling hills and experience the The Farm Art DTour. Held in a different location of Sauk County every year, the Fermentation Fest has a variety of things to see and do, but you can download the driving tour at the website and see it any day October 2-11. It is 50 miles but because you will be stopping to see things, maybe take some photos, and driving scenic roads, it will take more than an hour. Someone told me they did all the stops and it took them 4 hours...just so you plan enough time before it's dark.