Whether you'd rather spend a cozy weekend retreat in a fireplace suite with a brisk walk in a charming small town winter setting, or you'd rather sport your winter gear and hit the outdoors—don your favorite pair of mitts and prepare for fun in Sheboygan.

Relax with incredible views of a wintry Lake Michigan spangled with floating icebergs and crisp waves at the Blue Harbor Resort & Spa. Book a dinner and a show package with the GrandStay Hotel—winter walking distance from fine dining at Marguax and the Stefanie H. Weill Center for the Performing Arts. Spend a weekend with friends on the Sheboygan River at the Harbor Winds Hotel and saunter through the Riverfront Shanty Shops. Plan a cozy weekend of movies, games and casual dining for the whole family with a condo stay at Harborside Villas. Tour the whimsical John Michael Kohler Arts Center for an array of exhibitions, galleries and shows.

If you'd rather Sheboygan outdoors, you won't find a more friendly spot nestled among a bustling outdoor recreational playground. Snowmobiling, cross country skiing, ice fishing and sledding are in fashion all winter long. Check out Sheboygan County Parks for trails and hills. Oh! And don’t forget, winter is surfing season in the City of Sheboygan, and you just might spy a surfer or two riding the best waves of the year—in thermal insulated wet suits, of course!

So how do you Sheboygan through Winter? Start by clicking "play" at the top of the page, then explore all the exciting ways to Sheboygan. Don't forget to pack your mittens!

I sled. I snowboard. I surf. I snowmobile. I ski. I ice fish. I relax. I dine. I entertain. I am entertained. I Sheboygan.