The Osthoff Resort’s Christmas Tree Lighting
2025-12-04 17:00 - 18:30 (America/Chicago) | The Osthoff Resort, 101 Osthoff Avenue, Elkhart Lake, 53020, United States
Celebrate the holiday season at The Osthoff Resort with the Grand Christmas Tree Lighting. Enjoy the glow of the tree, festive music, and the spirit of the season. Bring your family and friends and make lasting memories at this cherished holiday tradition.

Making Spirits Bright
2025-12-04 17:00 - 21:00, 2025-12-05 17:00 - 21:00, 2025-12-06 17:00 - 21:00, 2025-12-07 17:00 - 21:00, 2025-12-08 17:00 - 21:00, 2025-12-09 17:00 - 21:00, 2025-12-10 17:00 - 21:00, 2025-12-11 17:00 - 21:00 and 1 more date | Evergreen Park, 3030 Calumet Dr, Sheboygan, WI, 53081, United States
Making Spirits Bright is a spectacular drive-through holiday lights show located at Evergreen Park in Sheboygan. This annual event, initiated by the Sheboygan County Rotary Clubs in 2012, runs from the Friday after Thanksgiving through New Year’s Eve, from 5:00-9:00 p.m. nightly, except for December 24th. The show is free of charge, but guests are encouraged to bring donations of food and hygiene items for the Sheboygan County Food Bank. In addition to the light show, there are indoor activities at the Sheboygan Jaycees Quarryview Center on Fridays and Saturdays through December 20, including visits with Santa, wreath raffles, musical entertainment, and concessions. Making Spirits Bright, made possible through the hard work of 1,700 volunteers, is a cherished holiday tradition that attracts visitors from across Wisconsin and neighboring states.

Old World Christmas Market at The Osthoff Resort
2025-12-05 10:00 - 17:00, 2025-12-06 10:00 - 17:00, 2025-12-07 10:00 - 17:00, 2025-12-08 10:00 - 17:00, 2025-12-09 10:00 - 17:00, 2025-12-10 10:00 - 17:00, 2025-12-11 10:00 - 17:00, 2025-12-12 10:00 - 17:00 and 1 more date | Osthoff Resort, 101 Ostoff Ave, Elkhart Lake, WI, 53020, United States
The 2025 Old World Christmas Market is open daily from 10 AM – 5 PM, December 5-14, 2025. Admission is $7 per adult, children 14 and under are complimentary with an adult ticketholder. Discounted ticket prices for groups of 20 or more are available. Reminiscent of the centuries-old Christkindlesmarkt of Nüremberg, Germany, the 27th annual Old World Christmas Market at The Osthoff Resort offers the warmth and merriment of this Old World tradition.
For ten consecutive days, guests stroll the aisles of a grand heated tent bedecked with fragrant boughs of fresh evergreens and the tantalizing scents of roasted almonds as they browse for unique and specialty items among international and regional artisans. Czech blown-glass ornaments, Russian nesting dolls, German hand-carved smokers and nutcrackers, fine apparel, handmade amber and silver jewelry, Turkish pashmina scarves and shawls, stained glass art, Russian hand-painted Santas, fresh green wreaths, kissing balls and centerpieces, alpaca products, Estonia woolens, fine chocolates, Plauen lace, fine woodwork, fur products and much more!

Holiday Memories
2025-12-05 12:00 - 17:00, 2025-12-06 12:00 - 17:00, 2025-12-07 12:00 - 17:00, 2025-12-08 12:00 - 17:00, 2025-12-09 12:00 - 17:00, 2025-12-10 12:00 - 17:00, 2025-12-11 12:00 - 17:00, 2025-12-12 12:00 - 17:00 | Sheboygan County Museum, 3110 Erie Ave, Sheboygan, WI, 53081, United States
Holiday Memories is a destination to create memories, alongside sharing in an experience of years past. A magical exhibition rooted in the animated holiday window displays of Sheboygan’s H.C. Prange Company store is accompanied by favorites Bruce the Spruce, vintage Garton Toys to pedal in the ride-on corral, and family-friendly activities. Visit the festively decorated Community Trees, the David Taylor House and Weinhold Log Cabin or dive into one of the many merry events scheduled. See the complete schedule at sheboyganmuseum.org.
Admission: Adult (18-61) $10, Seniors (62+) and Active Military $7, Youth (6-17) $5, Child (0-5) Free

Run Santa Run 5K at Blue Harbor
2025-12-06 09:00 - 11:00 | Blue Harbor Resort & Conference Center, 725 Blue Harbor Drive, Sheboygan, WI, 53081, United States
Step into a winter wonderland as the Blue Harbor Resort, transforms into a merry playground for the festive Run Santa Run 5K.
Lace up your running shoes and join the jolly crowd as hundreds of Santas, Elves, and Polar Bears take over the streets of Sheboygan, spreading holiday cheer with every step.
The festive atmosphere is contagious with a visit from Santa Claus, fun aid stations, and a race to stop the Grinch from stealing Christmas!
Whether you’re an avid runner or simply looking for a jolly good time, this spirited event promises laughter, holiday spirit, and a dash of competitive fun for all ages.
Here’s how to join in on the fun:
STEP #1: Decide whether you want to run or walk as a Santa, Elf, or Polar Bear.
STEP #2: Get your costume. We’ll help with character shirts and hats or accessories.
STEP #3: Run or walk the 5K and have a good time making sure to soak in all the holiday fun!
STEP #4: Enjoy the North Pole Post-Race party at Blue Harbor Resort!
Come for the race, stay for the fun—this holiday event promises a jolly good time for all ages!

Elkhart Lake Retail Holiday Open House
2025-12-06 12:00 - 16:00 | Elkhart Lake, 41 E Rhine Street, Elklhart Lake, WI, 53020, United States
Shop small and support local businesses this holiday season. Explore the shops of Elkhart Lake during their 14th Annual Holiday Open House and take advantage of special sales and promotions while enjoying delicious beverages and festive treats as you search for unique gifts for your loved ones. From cozy boutiques to charming specialty stores, you’ll discover a treasure trove of great gifts to check off your holiday shopping list.
Participating Shops:
Vintage Elkhart Lake,Gina’s Fine Gifts & Home Goods,Elkhart Lake Outfitters,Two Fish Gallery,The Intuitive Balance,STBF Shop,AspenOak,Nordic Accents,Gifts of Grace,Elevate Yoga Elkhart Lake,Art Room Elkhart Lake

Reindeer Brunch at The Osthoff Resort
2025-12-07 09:00 - 12:00 | The Osthoff Resort, 101 Osthoff Avenue, Elkhart Lake, 53020, United States
Celebrate the season with a holiday brunch featuring all your favorite seasonal dishes. Meet Santa’s real reindeer and enjoy a relaxed meal with family and friends. Kids will love seeing the reindeer up close and everyone can take photos to capture the festive moment.
Adults: $39.95
Children 10 & under: $14.95 (Tax and gratuity not included)
Cancellation Policy:A $20 per person fee applies for cancellations made less than 72 hours prior to the event.
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