Sheboygan, Wisconsin

Location: Lake Michigan

Ease of Getting There: 8/10

Ease of Staying There: 8/10

Ease of Eating There: 9/10

Sheboygan, Wisconsin, is a playground for the outdoor lover all year long.  It is known as a “freshwater haven” (why we LOVE the Great Lakes) and to the surf crowd, it is known as the “Malibu of the Midwest.” Sheboygan (not to be confused with Cheboygan, Michigan) is located on the western shore of Lake Michigan and juts out five miles into Lake Michigan, creating incredible waves when the wind comes in at 20-25.  The break along the five miles of coast create plenty of opportunities for surfers to catch a huge swell.  You can surf year-round, but peak season is September through March.  Of course, the peak season comes with 33-degree water temperatures and sub-zero wind chills.  Winter surfing is for the very intense and winter surfer fanatics can’t wait for this chilly, but invigorating season.

For the less adventurous enthusiasts, there are plenty of other outdoor activities to enjoy.  Fall brings Blue Water Craft Beer Festival, color tours, pumpkin picking and crisp bike and hiking trails.  Enjoy the full culinary experience Sheboygan has to offer as well as craft beer, wine and coffee.  So many delicious options!

Sheboygan is 2 ½ hours from Chicago and 6 ½ hours from Detroit by car.