Door County, WI
Driving time from Chicago: Three hours and 45 minutes
As the brisk autumn air descends on this summer hotspot, head to Potawatomi State Park, which offers 1,200 acres of hills and cliffs overlooking the bay on the southern end of the country. Walk along the Tower Trail, a 3.6-mile unpaved loop that takes you through dense forest and up to Old Ski Hill Overlook, which has been transformed into a lookout point. Stop for a snack and take in the gorgeous views of the tops of colorful trees and the bay. If you’re not up for a walk, this lookout point is also accessible by car.