The Top 14 Things Happening Around Sheboygan This Weekend

The Weekend Whassup for Friday, 5/16/2025! The Point keeps you connected to the top 14 things happening around Sheboygan this weekend! “The Weekend Wassup is brought to you by Pleasant View Realty’s – Matt and Nikki Capellen.”

Racing’s past comes to life this weekend as the Spring Vintage Weekend returns to Elkhart Lake’s Road America! https://www.roadamerica.com/spring-vintage-weekend-svra 

Sheboygan Theater Company Presents –  Legally Blonde the Musical on stage at Horace Mann Middle School with showtimes through this weekend! https://wxerfm.com/events/446224/ 

The 10th Annual Sheboygan A’s 5K Home Run/Walk is tomorrow (Saturday) morning at 8! Come for the walk/run and stay for opening weekend baseball back at Wildwood Baseball Park in Sheboygan! https://www.facebook.com/events/1955819028162494 

Flawless Hoops invites you to a benefit brat fry featuring live music from The String Benders tomorrow (Saturday) from 11-6 at Racer’s Hall in Plymouth. https://www.facebook.com/events/1774838536414978/ 

Gather In The Gardens to Benefit Sheboygan County Interfaith Organization is tomorrow (Saturday) from 9-4 at Christopher Farm and Gardens. Scavenger hunt, train rides, cash raffle, food, mini photo shoot, entertainment, kids crafts and more! https://www.sheboygancountyinterfaith.org/gather-in-the-gardens/ 

The 2nd Annual SLFSC Car Show is tomorrow (Saturday) at 2pm at Sheboygan’s Lakers Ice Center! https://www.facebook.com/events/547109537743228 

Cleveland Lions Annual Brat Fry is today (Friday) and tomorrow (Saturday) from 9-5 at Dairyland Park in Cleveland. Cleveland garage sales are this weekend too! https://www.facebook.com/events/1250249983188626/ 

Plymouth Dirt Track Racing action heats up again tomorrow (Saturday) evening at the fairgrounds in Plymouth. Pits after 2. Qualifying and racing after 4:30. https://www.plymouthdtr.com/schedule.html 

Brew City Wrestling Presents “Showdown in Sheboygan” tomorrow (Saturday) at 7 at Sheboygan Elks Lodge 299. https://www.brewcitywrestling.com/bcw-events/elks-lodge-299-4-12-25/ 

The Sheboygan Symphony Presents: Luminescence tomorrow (Saturday) night at 7:30 on stage at The Weill Center For The Performing Arts in Downtown Sheboygan. https://wxerfm.com/events/446253/ 

The Fred Astaire Dance Studios invite you to check out the world of competitive ballroom dancing this weekend at Sheboygan’s Blue Harbor Resort and Conference Center. Public spectators welcome! https://www.facebook.com/events/508529141938535 

The Marine Corps League Brat Fry is Sunday from 11-6 at VFW Post 9156 in Sheboygan. Brats, burgers, limited fried items, cash and 50-50 raffles. https://www.facebook.com/events/1147316890500619/ 

The Cascade Fire Department Hosts a car show and fundraiser, Sunday from 11-5. Grilled burgers, brats, chips, desserts, soda, water and beer. Meat and Bucket Raffles! https://www.facebook.com/events/673948632279248 

Food Trucks are back at BOTH Vollrath and Kiwanis Parks on Monday evenings from 4-8 through the summer! https://visitsheboygan.com/event/food-truck-mondays/57/