Sheboygan will sparkle with holiday spirit as the Run Santa Run 5K returns to the Blue Harbor Resort on December 6, 2025.

Locals can run or walk as a Santa, Elf, or Polar Bear, decked out in festive shirts, hats, and fun accessories.

The family-friendly race starts bright and early at 9:00 AM CST, bringing joy to Sheboygan’s winter streets for all ages.

Participants can collect their race materials early on December 5 from 4:00 PM to 7:00 PM at the resort’s Conference Center—setting the stage for a seamless race day.

After you cross the finish line, indulge at the North Pole Post-Race Party with hot chocolate, Christmas cookies, and drink tokens from 3 Sheeps Brewing.

Registration is now open at $35 for adults and $30 for children under 12, but fees rise after November 30.

This festive 5K promises a magical start to the holiday season in Sheboygan.

Making Spirits Bright lights up Evergreen Park in Sheboygan for its 14th year, enchanting visitors with a shimmering holiday spectacle set to festive tunes.

From November 28 to December 31, families can journey the 1.1-mile path glittering with over a million lights—an unforgettable seasonal tradition for all generations.

Admission is complimentary, but guests are urged to donate non-perishable food items, supporting the Sheboygan County Food Bank’s vital mission.

Last season, an outstanding 117,324 pounds of food were gathered, offering hope to many local families facing hardship.

Santa’s Station at 3401 Calumet Drive welcomes visitors on Friday and Saturday evenings through December 20, featuring Santa visits, festive music, raffle prizes, and tasty treats.

Cyclists can also join the Making Spirits Bright Holiday Group Ride on November 26, 2025, at 4:30 pm—encouraged to decorate bikes and contribute food donations.

The Sheboygan Theatre Company will bring the beloved play 'Steel Magnolias' to the stage from December 5 to 13, 2025, at the Leslie W. Johnson Theatre inside Horace Mann Middle School.

Set in a cozy Louisiana beauty salon, this warm, witty production follows a close-knit group of Southern women as they navigate both joys and hardships, highlighting the enduring power of community and friendship.

Directed by Lauren Shields, whose experience spans regional and Off-Broadway work, the show stars local favorites like Emily Golabiewski, Katie Tipton, and Jade Henschel.

Evening performances begin at 7 p.m. on December 5, 6, 11, 12, and 13, with matinee options at 2 p.m. on December 7 and 13.

Tickets range from $11 to $23 and are available through the Sheboygan Community Recreation Department.

Experience a story filled with laughter, resilience, and heartfelt moments live in Sheboygan.

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The Second Annual Pick-El Ball Tournament will bring the community together on Saturday, December 6, at the Sports Core in Kohler, Wisconsin.

This spirited indoor pickleball event aims to raise awareness for mental health and bolster suicide prevention efforts.

Players age 14 and up are invited for doubles competition — whether women’s, men’s, or mixed brackets — with each team guaranteed at least four games.

The tournament honors the memory of Elli Zahn Westfall, lost to depression in 2014, as her loved ones strive to inspire important conversations about mental wellness.

Proceeds support Mental Health America of the Lakeshore, providing essential resources to Sheboygan County, where mental health challenges among youth remain acute.

Attendees can enjoy games, a silent auction, raffles, and community activities, making every participant a part of Elli’s legacy and crucial local mental health programming.

🌟 **Welcome to Harry's Diner!** 🌟

Step into the charming world of Harry's Diner, located in the heart of Sheboygan! Whether you're a local food enthusiast or a traveler passing by, Harry's Diner offers a delightful experience that combines traditional diner vibes with a modern twist. 🍽️✨

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Harry's Diner - Where great food, good company, and unforgettable memories are served daily! 🍽️❤️

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