This was Tira’s first fall, and this is the perfect Wisconsin fall day trip from Chicago. We built the whole day around chasing Wisconsin fall foliage without going too far from Chicago. Kettle Moraine, Holy Hill, and a stop at Leon’s Frozen Custard on the way home turned into one of our favorite low key fall days yet, and it easily fits into a single day trip.

---

Stop 1: Kettle Moraine State Forest, Northern Unit

The Drive In: Kettle Moraine Scenic Drive

Part of what makes this stop worth the trip is the drive itself. The approach into the Northern Unit follows a stretch of the Kettle Moraine Scenic Drive, a 115 mile route that winds through all five units of the forest along the actual ridgeline the glaciers left behind. In fall, this is not just a way to get to the trailhead, it is a preview of the color to come, rolling hardwood forest the whole way in.

Parnell Tower

The tower itself is a 60 foot wooden observation structure, and it is where you get the real payoff view, up to 25 miles out over the surrounding hills and farmland on a clear day. It is a quick climb up a series of steps, and it is genuinely worth the stop even if you are not planning to do the full loop.

Dogs are not permitted up the tower itself, only on the trail below it, so if you are hiking with a pup, someone will need to wait at the base while the other climbs.

The Loop Trail

From the tower, the trail continues into the full 3.5 mile loop, winding through the rest of the forest before bringing you back to the parking area. This is where Tira got to join in fully, leashed dogs are welcome on the trail itself, and the fall color along this stretch is what makes the whole hike worth planning a trip around. The temperatures were perfect that day, and what we loved most was how dreamy it felt with the leaves falling around us.

Good to know: A Wisconsin State Park vehicle admission sticker is required for parking at the trailhead. Leashes must be 8 feet or shorter. View the Parnell Tower Loop on AllTrails before you go to check current conditions.

---

Stop 2: Holy Hill, Wisconsin

Holy Hill is not a hike in the traditional sense, but it earns its spot on this list.

The Basilica sits at the highest elevation point in southeastern Wisconsin, and its Scenic Tower is a 178 step climb to sweeping views over the surrounding countryside. Below it, the grounds are open to wander, including the Stations of the Cross garden.

We first saw it in fall, and it was simply majestic. But the line to climb the tower was long that day and we never made it up. We came back the following summer with my sister and mom, and the views from the top were incredible, though the whole time I kept imagining how beautiful they must be with fall color stretching out below. If you are anywhere near this part of Wisconsin in October, put climbing the tower in fall on your bucket list, we would go back for that view alone.

Tira has been with us both times. We skipped the tower entirely on our fall visit because of the line, and on our summer visit we took turns climbing so one of us always stayed with him on the grounds, since dogs are not permitted inside the tower or the Basilica. 🐾

Plan ahead: Go early if you are visiting in fall, or expect a wait for the tower. The Scenic Tower is only open May 1 through October 31, so plan your fall visit before it closes for the year. Admission to the grounds, Basilica, and tower is completely free. If you get hungry, the Holy Hill Cafe is known for its pie, the Fruits of the Forest is the one to try.

---

Stop 3: Leon’s Frozen Custard, Milwaukee

We ended the day the way we always do when we are in Wisconsin: a stop at Leon’s Frozen Custard. It is a Milwaukee institution that has been serving custard from the same classic drive in since 1942, and it has become a tradition for us whenever we are in the area before heading home.

This one is an absolute must for us. We love their custard, and part of the fun is going at different times of year since they rotate seasonal flavors. One visit they had raspberry and it was delicious.

There is no indoor seating, it is a walk up window with a parking lot to enjoy your custard in, which makes it easy for dogs too. Pop your trunk open, sit on the tailgate, and enjoy your custard right there. The employees are always kind and will offer Tira a small custard of his own. 🐾

---

Want to Make It an Overnight Trip?

This loop works perfectly as a single day trip, but if you want to slow it down, Milwaukee sits right at the end of the route and makes an easy place to stay the night instead of driving straight home. Spend a relaxed morning exploring the Milwaukee lakefront, the Historic Third Ward, or one of the city’s breweries before heading back to Chicago.

Want to see every lodging option in Milwaukee mapped out at once? Here is a quick look.

Prefer to Camp Closer to the Trailhead?

If you would rather stay closer to Kettle Moraine, the Long Lake and Mauthe Lake campgrounds are both within the Northern Unit and make for a genuinely peaceful fall camping option if you want to catch the color at sunrise. Reservations run through the Wisconsin state park booking system.

---

What We Packed for This Trip

• Hiking shoes with grip for the Parnell Tower steps
• Collapsible water bowl for Tira on the trail
• Reusable water bottle, there are no water stations along the Parnell loop
• A light jacket, fall mornings in Wisconsin get cold fast
• Car phone mount for the drive

See our full Hiking Essentials and Road Trip Essentials pages for everything we pack, and our Pet Travel Gear for Tira page for what we bring for him specifically.

Dog Friendly Notes

🐾 Both Kettle Moraine and Holy Hill welcome leashed dogs, with a few restrictions worth knowing before you go. Dogs are not allowed inside the Holy Hill tower or Basilica, only on the surrounding grounds. At Kettle Moraine, leashes must be 8 feet or shorter, and dogs are not permitted on a few designated nature trails elsewhere in the forest, though the Parnell Tower Loop is not one of them. Leon’s Frozen Custard has no indoor seating, so it is an easy, relaxed stop for a pup at the end of the day.

Final Thoughts: Is a Wisconsin Fall Day Trip from Chicago Worth It?

Absolutely! This is one of the easiest fall day road trips we have done from Chicago, and it does not require a single overnight to make it feel like a real getaway. A hike with a view, a hill with a history, and custard to close it out, that is a hard combination to beat. If you have more time, turning it into an overnight in Milwaukee or camping at Kettle Moraine is an easy way to stretch it into a full weekend.

Have you hiked Kettle Moraine or climbed the tower at Holy Hill? Drop a comment below, we would love to hear your favorite fall stops in Wisconsin.

More Fall Road Trips & Hiking Guides