Making Spirits Bright
2025-12-21 17:00 - 21:00, 2025-12-22 17:00 - 21:00, 2025-12-23 17:00 - 21:00, 2025-12-25 17:00 - 21:00, 2025-12-26 17:00 - 21:00, 2025-12-27 17:00 - 21:00, 2025-12-28 17:00 - 21:00, 2025-12-29 17:00 - 21:00 (America/Chicago) and 2 more dates | 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.

Holiday Memories
2025-12-22 12:00 - 17:00, 2025-12-23 12:00 - 17:00, 2025-12-26 12:00 - 17:00, 2025-12-27 12:00 - 17:00, 2025-12-28 12:00 - 17:00, 2025-12-29 12:00 - 17:00, 2025-12-30 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

Kohler Presents: Mahjong Weekend
2026-01-23 - 2026-01-25 | WI
Mahjong is having a major moment—join certified instructors Kitty Gaenslen and Amy Lukas for a lively winter weekend retreat where you’ll master the game with a unique mix of strategy, skill, and fun.

Comedy Night
2026-01-31 19:30 - 22:00 | WI
Get ready for an unforgettable night of laughs at The American Club as touring comedians John Heffron, Kelly Collette, and AJ Leidig take the stage.

Easter Brunch at The Osthoff Resort
2026-04-05 10:00 - 14:00 | The Osthoff Resort & Spa, 101 Osthoff Avenue, Elkhart Lake, 53020, United States
Join The Osthoff Resort & Spa for Easter Brunch on April 5th, 2026, from 10AM to 2PM. Enjoy a delectable feast with family and friends on Easter morning with a buffet featuring slow‑roasted Prime Rib, Omelet Station, tender Herb‑Roasted Chicken, BBQ Ribs with Apple Cider BBQ Sauce, and Baked Cod with Lemon Butter. Save room for indulgent desserts, especially the White Chocolate Fountain and house‑made cakes.
Adults $59.95 | Kids 6–12 $19.95 | 5 & under free (Pricing is per person plus taxes & gratuity)
*A $20 per person fee will apply for cancellations made less than 72 hours prior to the event.
Reserve Your Spot

Plymouth Maple Festival
2026-04-11 09:00 - 13:00 | Plymouth City Park, 203 Suhrke Street, Plymouth, WI, 53073, United States
This fun event celebrates maple sugaring season in and around the Kettle Moraine State Forest!
Local maple syrup producers will be on hand to demonstrate the tree-tapping and syrup-making process. Peruse local maple products, participate in kids’ activities, and celebrate the start of spring with your neighbors and friends!
St. Paul’s Episcopal Church will be serving up a delicious pancake breakfast, featuring real maple syrup and maple breakfast sausage.
There will also be a Maple Dinner on Friday, April 10th at Nourish Farms before the festival. Tickets will be available soon!

10th Annual Shop & Sip Elkhart Lake
2026-04-25 12:00 - 17:00 | Elkhart Lake, 41 E Rhine Street, Elklhart Lake, WI, 53020, United States
Join the Shops of Elkhart Lake for the 10th Annual Shop & Sip! Spend the day shopping and sipping your way through downtown Elkhart Lake.
YOUR TICKET INCLUDES THE FOLLOWING:

Elkhart Lake Stemless Wine Glass
A Shopping Tote
$5 Shop & Sip Cash Voucher
Shopping Passport & Map
List of Shopping Deals & Wines at each location
Snacks

Make a stop at each of the participating Elkhart Lake businesses to be entered to win a variety of prizes.
TICKETS: Tickets must be purchased in advance. (Tickets on COMING SOON!)
Tickets will be NOT be available for purchase on the day of the event, and there is a limited quantity available.
SHOPS & GALLERIES

Paddock Shop at Road America – Event Starts Here with Registration & Check-In
Quit Qui Oc Pro Shop
AspenOak
Aspira Spa Boutique (Located in The Osthoff Resort)
Gina’s Fine Gifts / Elkhart Lake Outfitters
Intuitive Balance
Nordic Accents
Elk Trader Gift Shop (Located in The Osthoff Resort)
STBF Shop
Schamberger Gallery
Two Fish Gallery
Vintage Elkhart Lake

Jazz on the Vine
2026-05-01 - 2026-05-02 | Osthoff Resort, 101 Ostoff Ave, Elkhart Lake, WI, 53020, United States
Welcome to Jazz on the Vine, a three-night live music event centered around the appreciation for jazz. The intimate inside event space offers the unique chance to experience up-close and dynamic performances by world-renowned jazz musicians. The core audience of our loyal jazz patrons and adventurous travelers creates a relaxed ambiance, where sitting back in your chair or letting your hair down to dance in the back are equally encouraged.

Mother's Day Brunch at The Osthoff Resort
2026-05-10 10:00 - 14:00 | The Osthoff Resort & Spa, 101 Osthoff Avenue, Elkhart Lake, 53020, United States
Celebrate Mom with a brunch she won’t forget. Treat her to a delicious, thoughtfully curated spread featuring made-to-order omelets, Belgian waffles, fresh salads, and carved prime rib, plus a decadent dessert selection including Snickers cheesecake, strawberry shortcake, and classic cannoli.
Join The Osthoff Resort from 10 AM–2 PM. Every mom will be welcomed with a fresh flower and a complimentary glass of champagne, because she deserves something extra special.
Pricing:Adults (17+): $59.95Children: $1 per year of agePricing is per person, plus taxes, fees, and gratuity.
A $20 per person fee applies to cancellations made within 72 hours of the event.

Mother's Day Brunch at Road America
2026-05-10 10:00 - 14:00 | Road America, N7390 HWY 67, Elkhart Lake, WI, 53020, United States
Join Road America for a special Mother’s Day Brunch at the Road America Finish Line Tower Suites on Sunday, May 10th, from 10AM to 2PM. Enjoy a delicious brunch experience paired with exclusive access to premium viewing areas, offering a unique vantage point to take in all the sights and sounds of the 24 Hours of Lemons—a fun, family-friendly racing event included with your brunch ticket.
Pricing

$60 | Adults (includes event admission)
$50 | Brunch add-on (for guests with existing Sunday admission or credentials)
$35 | Children ages 3–10 (includes event admission)
$0 | Children 2 and under

$50 adult ticket available for those with an existing ticket to 24-Hours of Lemons.
Brunch Menu

Sauteed Smoked Brisket Skillet – mixed with scrambled eggs, potatoes, and cheese
Belgian Waffles – Maple syrup, fruit preserves, fresh Wisconsin butter & whipped cream
Fresh Fruit Salad
Assortment of Breakfast Pastries
Coffee, Tea, Juice, Water, & Soda
Cash bar for beer, wine, and mixed drinks

SVRA Vintage Festival Weekend
2026-05-15 - 2026-05-17 | Road America, N7390 HWY 67, Elkhart Lake, WI, 53020, United States
Racing’s glorious past comes to life as the Spring Vintage Weekend with SVRA returns to Road America. The season kick-off event will showcase all the sights and sounds from motorsport’s pioneering age to modern-era racecars.
The event features a packed schedule. Races will feature cars spanning several decades — many of the entries having previously competed at Le Mans and the Indy 500.
SVRA (Sportscar Vintage Racing Association) SpeedTour events offer tightly regulated, wheel-to-wheel racing with a lineup that includes race groups for all SVRA classes. Classes include Formula 5000, Formula Ford, sports racing, and production sports cars from marques such as Lotus, Alfa Romeo, Jaguar, Porsche, and Corvette from the ’50s, ’60s, and ’70s.

Driftless Revelers & Davey and The Midnights (Live Music)
2026-05-22 19:00 - 22:00 | 3 Sheeps Brewing Company, 1837 North Avenue, Sheboygan, WI, 53081, United States
Davey & the Midnights & the Driftless Revelers are rolling into Sheboygan, WI. for a night of unconventional country music, rock & roll, and freak folk from Indiana and Eau Claire, Wisconsin. Come for some beers, stay for the music and good vibes.

Elkhart Lake's Farmers & Artisans Market
2026-05-23 08:00 - 12:00 | Elkhart Lake, 41 E Rhine Street, Elklhart Lake, WI, 53020, United States
Elkhart Lake’s Farmers & Artisans Market in the Village Square is a Saturday morning tradition. Pick up fresh seasonal vegetables, flowers, cheeses, local arts and specialty products from approximately 50 vendors. Every item sold is produced locally in the state of Wisconsin by the person right behind the stand! Grab your reusable grocery bags and head to the square every Saturday morning.

Sheboygan Memorial Day Parade
2026-05-25 09:00 - 12:00 | Downtown Sheboygan, 8th Street, Sheboygan, WI, 53081
Sheboygan’s Memorial Day celebration is a collaboration between United States Veterans and active-duty personnel, the City of Sheboygan, the Sheboygan County Veterans Service Office and Launch: Lakeland Student-Run Businesses. Kohler Credit Union is sponsoring the parade. The parade will be held on Monday, May 25, 2026, in downtown Sheboygan starting at 9:00 am with a ceremony to follow at Fountain Park.
Parade info:

The parade route starts at 7th Street & Center Avenue, goes north on 7th Street to Michigan Avenue, goes west on Michigan to 9th Street, goes south on 9th Street, and ends at Fountain Park

Ceremony info:

Begins immediately after the parade at Fountain Park
Tributes to veterans and active-duty men and women

Brat Fry info:

Begins immediately after the parade at Fountain Park
100% of proceeds will go to the Military and Youth Foundation and Marine Corps League.

MotoAmerica Superbikes & Vintage MotoFest
2026-05-29 - 2026-05-31 | Road America, N7390 HWY 67, Elkhart Lake, WI, 53020, United States
MotoAmerica Superbike races are returning to America’s National Park of Speed on May 29-31, 2026. Enjoy qualifying on Friday and all-day racing Saturday & Sunday. Five classes of road racing will compete, including Superbike, Motovation Supersport, Parts Unlimited Talent Cup by Motul, Mission King Of The Baggers, and SC-Project Twins Cup. Meet the riders in our open race paddock! Camping, VIP, and Fan Lap packages are available. Saturday, May 30th, features Vintage MotoFest, which includes a ride-in bike show and competition, live bands, and stunt shows.
On Friday night, May 29th, fans can check out the Dairyland Classic Flat Track Races at the Plymouth Fairgrounds. A FREE shuttle will be available at 5 p.m. at Gate 4 to transport campers and fans to and from the Plymouth Fairgrounds.
Vintage MotoFest
A highlight of the MotoAmerica Superbike weekend is Road America’s Vintage MotoFest presented by Revolution Performance on Saturday, May 30th. Regarded as the premier Wisconsin ride-in vintage motorcycle show and party featuring an eclectic mix of Euro, Japanese, and American vintage motorcycles. All makes and models are welcome! Enter your motorcycle upon arrival Saturday morning between 9-11AM.
