9 Best Annual Events in Sheboygan to Plan Around

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Sheboygan’s calendar is packed with exciting events that bring the whole community together year-round. Located along the beautiful Lake Michigan shoreline, the city hosts a number of festivals and celebrations that showcase its rich heritage and vibrant arts scene.

Sheboygan truly stands out with its dedication to offering unforgettable experiences throughout the year. Whether you're drawn to live music performances, cultural events, or family-friendly outings, the city’s vibrant event calendar has something special for everyone.

Don’t miss out on the excitement—book your stay with Sheboygan Vacation Rentals today to be close to all the action and enjoy comfortable accommodations.

1. Sheboygan Polar Bear Plunge

Photo Credit: Nancy Myers-Scholz

The Sheboygan Polar Bear Plunge is a thrilling annual event where brave participants dive into the icy waters of Lake Michigan to kick off the new year. This chilly tradition attracts locals and visitors alike, creating a festive atmosphere filled with camaraderie and excitement.

Spectators can enjoy the lively crowd, warm refreshments, and community spirit as everyone celebrates this unique way to welcome the year ahead. Whether you're taking the plunge or cheering from the beach shores, this event is a fun and invigorating way for the whole family to embrace the winter season in Sheboygan.

2. Sheboygan LGBTQ+ Pride Picnic

Photo Credit: Iryna Imago

The Sheboygan LGBTQ+ Pride Picnic is a welcoming summer event at City Green that brings the community together for an afternoon of celebration, connection, and visibility.

Typically held in a local park during Pride Month, the picnic features food, music, local vendors, and family-friendly activities in a relaxed, inclusive atmosphere. Locals appreciate its low-key, grassroots feel—more community gathering than large festival—making it easy to attend, support local organizations, and enjoy Pride in a way that feels authentically Sheboygan.

3. Juneteenth Celebration

Photo Credit: Svet foto

Juneteenth in Sheboygan is a vibrant, free community event celebrating African American heritage and freedom. Organized by the Sheboygan County Black American Outreach, the celebration features live music, cultural performances, educational activities, book readings, and delicious food from local vendors.

Families and visitors gather at Kiwanis Park to honor the historical significance of Juneteenth while enjoying a day filled with fun, learning, and community spirit. This inclusive event fosters awareness and appreciation of African American culture, creating meaningful connections among attendees of all ages and backgrounds.

4. Sheboygan Fourth of July Freedom Fest

Photo Credit: lavsketch

  • Kiwanis Park, 726 Kiwanis Park Rd, Sheboygan, WI
  • July 3-4, 2026

The Sheboygan Fourth of July Freedom Fest is a vibrant annual celebration honoring Independence Day with a full slate of family-friendly activities. The event features live music performances, food vendors offering classic American fare, carnival rides, and games for all ages. There's also the city's famous Venetian Boat Parade.

Locals know to claim a spot early along the shoreline or harbor walk for prime fireworks views, then stick around after the show to avoid traffic. It’s a classic Midwest Fourth of July done right—laid-back, patriotic, and scenic.

5. Midsummer Festival of the Arts

Photo Credit: Karen Dole

The Midsummer Festival of the Arts is a vibrant annual celebration showcasing the talents of local and regional artists. Visitors can explore a variety of art forms, including paintings, photography, jewelry, wood carvings, textiles, and more.

The festival features live music, food vendors, and interactive activities that create a lively and engaging atmosphere. This event brings together artists, families, and other members of the Sheboygan community for a memorable summer weekend filled with creativity and fun.

6. Brat Days

  • Kiwanis Park, 726 Kiwanis Park Rd, Sheboygan, WI
  • brat-days.com/
  • August 2026 (Upon publication, the specific dates for this year's Brat Days haven't yet been released. Keep an eye on the official event page for further updates.)

This traditional Wisconsin festival celebrates bratwurst with numerous vendor offerings, including brat tacos and brat pizzas. The event features live music, family activities, a brat eating contest, and a parade that draws visitors from across the region.

Brat Days creates a lively and festive atmosphere that highlights local culture and culinary delights. Attendees get to enjoy a day filled with fun, food, and community spirit in the heart of Sheboygan.

7. Levitt AMP Sheboygan Music Series

Photo Credit: TonStocker

The Levitt AMP Sheboygan Music Series is a summer favorite, bringing free, live music to the lakefront at Jaycee Park. Running on select evenings throughout the summer, the series features nationally touring and emerging artists across genres, all in a relaxed, community-driven setting.

Locals recommend bringing lawn chairs or blankets, arriving early for a good spot near the stage, and making an evening of it by walking along Lake Michigan before the show. It’s one of the best ways to experience Sheboygan’s arts scene without spending a dime.

8. Sheboygan Falls Oktoberfest

Photo Credit: katjen

  • Downtown Sheboygan Falls, WI
  • facebook.com/kohlerfallsoktoberfest/
  • Dates: September 2026 (Upon publication, the specific dates for this year's Oktoberfest haven't yet been released. Keep an eye on the official event page for further updates.)

In the nearby town of Sheboygan Falls, Oktoberfest is a lively annual celebration that honors Germany's rich heritage and culture. The event features authentic German food, traditional music, and festive beer gardens, creating a vibrant and welcoming atmosphere for all ages. Families can enjoy a range of activities, while live polka bands fill the air with energetic tunes.

Visitors love strolling through the charming streets of Sheboygan Falls, sampling classic German dishes and beverages. This festive fall event is a must-visit for anyone looking to experience the warmth and spirit of the season in the area.

9. Making Spirits Bright

Photo Credit: MLReed

Making Spirits Bright is a must-see Sheboygan holiday tradition, transforming Evergreen Park into a festive, drive-through light display each winter. Held nightly from late November through the Christmas season in December, this free event is easy to enjoy with kids, friends, or visitors—just tune your radio, roll through at your own pace, and take in thousands of synchronized lights.

Locals know the best time to go is early evening on a weekday to avoid lines, and bringing a donation for the Sheboygan County Food Bank is encouraged. It’s low-stress, high-impact holiday cheer and one of the city’s most beloved seasonal traditions.

Stay Near the Best Events in Sheboygan

Throughout the year, Sheboygan comes alive with a vibrant array of events that celebrate its rich culture, heritage, and community spirit. Visitors and locals alike find countless opportunities to engage with the community along Wisconsin’s beautiful Lake Michigan shoreline, making every season a perfect time to explore and enjoy Sheboygan’s dynamic event scene.

Plan your visit today and experience the best of Sheboygan events by booking your stay with Sheboygan Vacation Rentals. At our properties, you can enjoy comfortable accommodations that put you close to all the exciting festivals, concerts, and community gatherings happening throughout the year.

Featured Image Credit: James Meyer