10 Things to do in Sheboygan During Fall and Winter

Discover Wisconsin

October 20, 2016

Many of us have childhood memories of traveling to Sheboygan during our summer vacations for all kinds of warm-weather family activities. We’re here to prove, however, that Sheboygan is worthy of a visit during the fall and winter months as well. Belly-warming beer and brats, rides on a Segway and horse-drawn wagons, and twinkling holiday displays all make Sheboygan a place to stop this season.

  1. Take in the fall colors while learning about the history of Sheboygan with Sheboygan Segway Tours

    Photo courtesy of Sheboygan Segway Tours

    Photo courtesy of Sheboygan Segway Tours

    Sheboygan Segway Tours is a family owned and operated business, leading small groups on tours through the Sheboygan area where you can learn about the area’s history and take in the beautiful lakefront sights. What better time to ride around the city than when surrounded by the orange, red and yellow hues of autumn?

  2. Enjoy traditional German food, music, and of course, beer at Al & Al’s Steinhaus during their annual Oktoberfest celebration

    Photo courtesy of Al & Al's Steinhaus

    Photo courtesy of Al & Al’s Steinhaus

    Sheboygan is notoriously German, and Al & Al’s Steinhaus is Sheboygan’s Authentic German Restaurant, so I’m pretty sure there’s no choice but to go there during your stay, especially during its annual Oktoberfest celebration. The family-owned and operated business has been a Sheboygan favorite for 54 years and its authentic Oktoberfest celebration during the first weekend of October is a must.

  3. Sample hundreds of craft beers from all over the Midwest at the Blue Harbor Craft Beer Festival

    Sticking with the beer theme, Blue Harbor Resort hosts its annual Blue Harbor Craft Beer Festival, where you’ll find “the region’s best brews with the best views.” Visitors can sample more than 100 craft beers from 30 brewers and take home a souvenir glass.


  1. Sink your teeth into a delicious Sheboygan brat plate at Sly’s Midtown Salooon. (Order your brat with mustard and onions in true Sheboygan style!)
    Photo courtesy of Sly's Midtown Saloooon

    Photo courtesy of Sly’s Midtown Salooon

    Sheboygan is the Bratwurst Capitol of the World, so you can’t leave without trying Sly’s Famous Sheboygan Double Brat Plate, complete with mustard and onions (the sides of baked beans and homemade American potato salad don’t hurt, either). Sly’s is open 6 a.m. to close, seven days a week and 365 days a year, and its 69-foot bar, 50-inch TVs and family-friendly atmosphere make it a place for everyone.

  2. Check out the taproom at 3 Sheeps Brewing – Sheboygan’s very own craft brewery

    Photo courtesy of 3 Sheeps.

    Photo courtesy of 3 Sheeps

    Okay, last beer thing, I swear. 3 Sheeps Brewing Company was founded in 2011, but you’d think this five-year-old company was founded 100 years ago based on the taste and the experience you get here. The names of the beers alone are sure to pique your interest: Rebel Kent the First, Really Cool Waterslides, Baaad Boy, Cashmere Hammer, Hello My Name is Joe, First Kiss, Seven Legged Cartwheel, Autumnal Hoppiness and Ewephoria. Stop by on Fridays at 5 p.m. for a walk through the facility and to learn about the different steps of the brewing process (and maybe sneak a sip or two of its products).

  3. Enjoy the beauty of winter by snowshoeing, cross country skiing or hiking at Maywood Environmental Park

    Photo courtesy of Maywood Environmental Park

    Photo courtesy of Maywood Environmental Park

    The changing of the seasons is no reason to hibernate when places like Maywood Environmental Park exist. Listen to the crunchy leaves under your feet as you hike among the colorful autumn trees, or showshoe and cross-country ski through winter’s fresh powder.

  4. Make your own home décor at Urban Artique in downtown Sheboygan

    Photo courtesy of Urban Artique

    Photo courtesy of Urban Artique

    If being outdoors during the colder months isn’t really your thing, stop by Urban Artique to check out artwork done by over 40 independent artists (many pieces stick to a Wisconsin theme, which we approve of), or make your own home décor at one of the offered classes. Classes include reversible signs, barn quilts and open studio.

  5. Enjoy the animated holiday displays at the Sheboygan Historical Museum

    Photo courtesy of Sheboygan Historical Museum

    Photo courtesy of Sheboygan Historical Museum

    Sheboygan was home to the H.C. Prange Department Store for over 100 years, and its holiday spirit lives on through its original window animation, now displayed in the Holiday Memories exhibit at the Sheboygan Museum. Take in vintage holiday decorations, home-baked sweets, live entertainment, and even a visit from Santa Claus!

  6. Get into the holiday spirit at Sheboygan’s holiday lights display, Making Spirits Bright!

    Photo courtesy of Making Spirits Bright

    Photo courtesy of Making Spirits Bright

    The annual holiday lights display in Evergreen Park will be open every night between Thanksgiving and New Year’s Eve, while Quarryview Center across from Evergreen Park will be open on weekends and features Santa visits, concessions, entertainment and trolley rides. Admission is free, but donations for the Sheboygan County Food Bank are encouraged.

  7. Stop by the historic Wade House during their holiday celebration to see how people celebrated in the 19th century

    Photo courtesy of Wade House

    Photo courtesy of Wade House

    The Wade House Stagecoach Hotel opened to the public in 1850 and, to travelers, represented the prosperity and progress of the young village and state. It was once home to business meetings, political caucuses, court sessions and debates. 100 years later, in 1953, the Wade House opened to the public as a Wisconsin Historical site. Today, the Wade House is complete with a Visitor Center and Wesley W. Jung Carriage Museum and, during the holidays, A Wade House Christmas. During one weekend in December, the house recreates an authentic 19th century Christmas experience, with fresh evergreen garlands, holiday tales and horse-drawn wagon rides.

What do you do to stay busy during the fall and winter months? Share with us on social media using #DiscoverWisconsin. And be sure to stream Sheboygan – A Fall & Winter Retreat on discoverwisconsin.com!

Kristen Finstad is a member of the Discover Wisconsin crew. Having grown up in River Falls, attending UW-Stevens Point and now living in Madison, she’s a Wisconsin girl through and through. Watch Discover Wisconsin TV Saturday mornings at 10 on Fox Sports Wisconsin. (Twitter: @DiscoverWI)

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