The best time to visit Highland, Wisconsin, is during the summer months, from June to August, when the weather is warm and conducive to outdoor activities, or in the fall, from September to October, for the striking autumn foliage.Summer in Highland brings average temperatures in the 70s, making it ideal for exploring the area's natural beauty. You can enjoy hiking and biking on trails like those found in the Governor Dodge State Park, or spend time on the water at Blackhawk Lake. This season is particularly good for families looking for an active vacation.For those who appreciate scenic beauty, the fall offers cooler temperatures, typically in the 50s and 60s, and a spectacular display of changing leaves. This period is superb for couples seeking a peaceful getaway and picturesque drives through the Wisconsin Driftless Area.