Winter is usually the time of year when most people just want to simply stay inside, snuggle up in a blanket and drink some hot cocoa. Although there are days when winter creates a new definition of cold, there are days when the sun does come out! On days like this, it’d be a shame to miss an opportunity to get outside, enjoy the snow, and create memories with family and friends. 

Making Spirits Bright

This drive-through light show will help you celebrate the holidays from the warmth of your vehicle. Experience this festive show choreographed to holiday music along a 1.1-mile route through Evergreen Park. Visit once or as many times as you want! Admission is free but they gladly accept canned goods as donations.

Get More Information and Details

Holiday Memories

Enjoy “When I Dream of Christmas!!” Holiday Memories is an annual exhibit held at the Sheboygan County History Museum event revolves around their collection of H.C. Prange and Boston Store animated characters. Children can ride Garton Toy Factory toys and build their own. Visit the Taylor House with its “I Spy” game, and the Weinhold Log Cabin. Both are beautifully decorated for the season! Enjoy Storytime with Santa and live music on select dates.

Get More Information and Details


Vollrath Bowl is a pretty unique, and popular, place to sled. This 1930s amphitheater has tiered sides so you get an exciting change in velocity as you slide down (The tiers also make it easier to walk back up the hill if you aren’t near the stairs). Vollrath is great for little kids and adults alike. For a slightly smaller hill, head a little west and check out  Kiwanis Park.

Fat Bike around Sheboygan

“Fat biking” as it’s called, or riding bicycles with wider tires on approved snow-covered trails, is an increasingly popular sport in Wisconsin. Snow doesn’t slow the biking fun, but rather adds to it!

There are a few trails in the area. Greenbush Recreational trails (N5854 Kettle Moraine Drive Glenbeulah WI) are a little outside of Sheboygan, but there are 9 miles of single track. Trail passes and state park stickers are required. On the other hand, hang out at Evergreen (3000 Calumet Drive Sheboygan, WIor the Quarry (3401 Calumet Dr, Sheboygan, WI). The trails are mostly singletrack with a nice mix of climbing and descending.

If you want to learn more visit Fat Kats Mountain Bike Club on Facebook

Ice Fishing

Weather depending, marina ice fishing begins in December and goes through March. You can expect to catch anything from Rainbow Trout, Brown Trout, Northern Pike, Smallmouth Bass, Perch, Bluegill and many more. Be sure to bring the right gear. When ice fishing the marina use jigging poles, tip-ups or an automatic fishermen.

Get More Information and Details

Snowshoeing at Kohler Andrae State Park 

A moderate 1-mile snowshoe trail begins at the amphitheater and winds south through the wooded campground area. It loops back through the picnic area before returning to the beginning. The snowshoe trail is not groomed. Additional snowshoeing is available at the 2.5-mile Black River Trail and throughout the park. Snowshoeing is not allowed on the groomed ski trail.

Get More Information and Details

Sheboygan Lakers Ice Center

Get off the couch, take a day with your friends and go ice skating! Blue Line Ice Center is affordable for anyone; ice skate rentals are $3 and the admissions fee is $5. Public skating begins on Tuesday, Sept. 4th. Find the public skating schedule here.

Get More Information and Details


Experience Surfing 

During the winter months, the surfing action picks up here in Sheboygan. We’re not the “Fresh Water Surf Capital of the World” for nothing. Because of its location and geography, Sheboygan has some of the best waves on the Great Lakes. While there are opportunities to surf or watch the surfers in the summer, if you are looking for the best experience and the biggest waves, winter is the time to do it.

(Author’s note: Frozen beards and scaling small glaciers can be expected.)

Cross Country Skiing

Jaycee Cross Country Ski Trails:  There are a number of trails around this area. Each loop has a different color. Many of the loops are around the 1 mile mark. You can find yourself exploring Evergreen Park and Maywood. Some trails lead you south of the Pigeon River, near the Maywood Ecology Center, down illuminated night skiing trails. Click on the link to get specific route details. 

Get More Information and Details

Kohler-Andrae State Park: A 2-mile cross-country ski trail has flat to gentle slopes and takes you through a variety of beautiful environments. The trail starts near the amphitheater and travels through the wooded southern campground on unplowed roadways. It then hooks up to the Woodland Dunes Nature Trail and later loops through the picnic area back to the beginning. The trail is groomed on a regular basis pending snow conditions and weather. Winter trail map [PDF].

Get More Information and Details

Take the Polar Plunge

It happens every year since 1973, and even the bitter cold of winter can’t stop it. On January 1, people line up along the frigid waters of Lake Michigan with only one thing on their minds – jumping in. It sounds crazy, but that doesn’t stop anyone from dressing up in costumes, yelling “It’s not cold enough!”, and taking the plunge. This will be one way of bringing in the New Year!

Other Related Posts

Pop Up Shops

Pop Up Shops

The pop-up shop program adds vibrancy, interest, and variety to downtown Sheboygan. Check out the three shops we hope are here to stay!

5 Can’t Miss Sheboygan Festivals

5 Can’t Miss Sheboygan Festivals

Almost every weekend in Sheboygan there is a different festival or event taking place. Food, heritage, seasons and music create a patchwork of fun and entertainment for everyone!

(920) 335-0060
Toll-Free: (844) 952-0200



NEW Sheboygan Visitor Center

Coming 2020, find us on the corner of 8th Street and Riverfront Drive, on the Sheboygan River!

EXPERIENCE THE SCENIC ROUTE!Receive Our Monthly Newsletter

Join our email list to get insider tips from Rachel's Route and to plan your next trip!