05/20/2026
Spring Fling! A Celebration of Community and Springtime in Winter, Wisconsin
Winter, Wisconsin is ready to burst into spring—and there’s no better way to celebrate than with Spring Fling! The Northwoods comes alive with birdsong, budding trees, and Main Street will be buzzing with energy, laughter, and hometown bargains and good food. Mark your calendars for Saturday, May 23, 2026, and join us for a full day of fun during Memorial Day weekend.
Main Street Market & Vendor Fair
From 9 AM to 2 PM, Main Street and find local artisans and crafters lining the street with handmade goods, seasonal finds, and creative treasures. It’s the perfect time to get out, reconnect, and enjoy the simple pleasures. Vendors are still welcome—sign up at www.winterwi.com and be part of the excitement.
The Great Rhubarb Pie Contest & Auction
One of the surest signs of spring in the Northwoods is rhubarb popping up in backyard gardens—and that means it’s time for the Great Rhubarb Pie Contest! Bakers are invited to showcase their best recipes, from classic to creative, for a chance to win one of two $100 prizes. After judging, the pies will be auctioned off at the corner by the bank on Main Street. There will be plenty of other homemade rhubarb treats as well. This is a delicious celebration of the season’s first harvest.
Lutheran Church Pancake Breakfast
Start your day with the Zion Lutheran Church Pancake Breakfast, served from 8:00 to 10:30 AM. It’s a warm and welcoming way to kick things off—fresh pancakes, hot coffee, and friendly conversation before heading out to enjoy the day’s events just down Main Street.
Winter Lions Classic Car Show
Spring Fling wouldn’t be complete without the rumble and shine of classic cars! The Annual Winter Lions Classic Car Show at the Winter School parking lot brings together beautifully restored vehicles and proud owners ready to share their stories. Registration runs from 9 AM to 12 PM, with trophies awarded at 1 PM.
About Spring Fling
Spring Fling in Winter, Wisconsin is all about celebrating the return of sunshine, fresh air, and community connection. It’s the sound of laughter downtown, the smell of good food, and the joy of seeing neighbors and visitors come together to welcome a new season in true Northwoods style.
For updates and vendor information, watch the Sawyer County Gazette and visit www.winterwi.com.
Come celebrate the season—Spring has arrived in Winter!