January 2026 Events in Milton, WI: Find Fun Activities for You and the Family!
Looking for events to distract you from the January chill? Milton is popping with fun activities for you and the entire family. Below, you’ll find functions that are sure to capture your interest. Come back to our blog every month for more!
Stranger Things Trivia at Timber Hill Winery
Sad about the end of the Stranger Things saga? Timber Hill Winery is taking you back to the Upside Down! Join your neighbors for a rousing hour-long game of trivia at Timber Hill Winery.
January 2, 2026 6:00-7:00 PM
8220 N John Paul Road
Milton, WI 53563
Pop Up Book & Bake Sale at Milton Public Library
What could be better than books and sweet treats? The Red Cross Youth Club is raising funds for the Red Cross with this event. Shop for a variety of books, puzzles, and DVDs for all ages and grab a treat, too!
January 3-4, 2026, during library hours
430 E High Street
Milton, WI 53563
Live Music at Rubber Ducky Winery
Every weekend, head out to Rubber Ducky Winery for amazing musical talent. Grab a drink, sit back, and relax.
Every Weekend!
232 S Janesville Street
Milton, WI 53563
Live Music at Lucy’s Hideaway
Lucy’s Hideaway is getting in on the live music action! January 3rd’s guest is singer-songwriter, Matt Andrus. Matt has been producing music all over the Midwest for the past 20 years as a solo artist and with bands like “Andrus & the Mariners” and “The Daily Express.”
January 3, 2026 7:00 - 10:00PM
5847 E County Road N
Milton, WI 53563
Sourdough Workshop at Timber Hill Winery
If you’ve never made sourdough before, now’s your chance! Margaret from Blue Bird Custom Creations will guide you through everything you need to become a sourdough pro. You’ll learn everything from how to care for your starter to the basics of sourdough baking. Your ticket includes a live sourdough starter, detailed instructions, recipes, and a ready-to-bake loaf of sourdough bread.
January 5, 2026 5:00 - 7:00 PM
8220 N John Paul Road
Milton, WI 53563
Shopping at Sunny & Olive!
What about a little retail therapy? Sunny & Olive is the perfect place to find low-cost, high-quality clothing, books, and more. Since 2023, we’ve been the area’s go-to consignment shop where style meets sustainability. Stop by our shop whenever we’re open! Your wallet will thank you.
613 W Madison Avenue
Milton, WI 53563
Bouquets and Brunch at Timber Hill Winery
It’s time for the ultimate girls’ day out! Create a beautiful bouquet and enjoy a delicious brunch with your favorite people. Your $20 ticket includes all your supplies and flowers. Drinks sold separately.
January 11, 2026 4:00 - 7:00 PM
Movie Quote Trivia with Misfit Felines at Timber Hill Winery
Movie lovers, unite! Test your cinematic knowledge while competing with your friends. This event supports Misfit Felines, featuring raffles and opportunities to support at-risk cats. If you bring in a food donation for Misfit Felines, you’ll be entered into a special drawing.
January 16, 2026 6:00 - 7:00 PM
Masquerade Murder Mystery at Timber Hill Winery
Can you solve the case before the night is over? Everyone is encouraged to bring their best masquerade look to this murder mystery, but it’s not required. Your $55 ticket covers the murder mystery game and dinner.
January 17, 2026
Sunday Funday: Games and Puzzles at Milton Public Library
This event is fun for the whole family. People of all ages are invited to gather for a relaxing afternoon of board games, puzzles, and classic favorites like chess. All skill levels are welcome to attend.
January 18, 2026 12:00 PM - 3:30 PM
430 E High Street
Milton, WI 53563
Girls Night Out Rock County at Lucy’s Hideaway
Girls Night Out Rock County is dedicated to helping women expand their circle of friends and help give back to their community. Proceeds from this event help support ECHO of Janesville. Come for the friends, stay for the basket raffles and 50/50 raffle!
January 21, 2026 5:00 - 8:00 PM
5847 E County Road N
Milton, WI 53563
Tattoo Pop Up at Sunny & Olive
Sunny & Olive is hosting a tattoo pop up! Stop by our shop to get a gorgeous piece from a local artist. Slots are first come first served. Not into tattoos? Come by for giveaways and a wonderful shopping experience.
January 24, 2026
613 W Madison Avenue
Milton, WI 53563
Spread the Love Fundraiser at Milton Public Library
The Red Cross Youth Club is selling handmade, crocheted hearts as a fundraiser for the Red Cross. Stop in during library hours to purchase hearts to give away and/or hide to spread the love. Hearts are 50 cents each or 5 for $2.00.
January 26-31, during library hours
430 E High Street
Milton, WI 53563