May in Milton: Your Guide to Fun Community Events!
The winter blues are behind us, and it’s time to soak up all that Milton, WI has to offer. There’s no shortage of reasons to get out and explore this month. Learn about our community’s events below, and don’t forget to stop by Sunny & Olive whenever we’re open!
Spring Into Trivia Fundraiser at The Gathering Place
This event is a whole lotta fun AND it gives back to our wonderful city! Proceeds benefit The Milton Fund, an organization that raises funds to donate back to the community. Gather your smartest friends and enjoy a night of prizes, community, and laughs.
May 1, 2026
6:00 - 9:00 PM
The Gathering Place
Connect with the Earth Herb Workshop at Blackhawk RV Campground
Need a way to decompress? This workshop is the perfect solution! During this event, you’ll learn about the impact of plants on mental health and gain insights into herb knowledge and care. Plus, you’ll walk away with your very own herb planter and recipes to make the most of your new herb garden. Registration is required and the cost for this event is $42.
May 2, 206
10:00 AM
Blackhawk RV Campground
Kelly Kreations Pop-Up at Sunny & Olive
What could be better than thrifting with snacks? Come down to Sunny & Olive to find the best secondhand treasures while snacking on a cake pop from Kelly Kreations.
May 2, 2026
10:00 AM - 3:00 PM
Sunny & Olive
My Son & I Dance at The Gathering Place
The Gathering Place is hosting a wonderful event for caregivers, single parents, and guardians to have a meaningful evening with their sons.
May 2, 2026
6:00 - 9:00 PM
Goodrich Square Book & Brew Fair at Good Works Brewing
Goodworks Brewing is bringing together four of the best independent bookshops around! Browse reads from Elmside Goods, Maze Books, Tattooed Tree Books, and The Rogue Bookstore. You’ll find everything from well-loved classics to hidden gems you won’t find anywhere else. And, you can enjoy a cold pint while you browse the stacks!
May 3, 2026
10:00 AM - 4:00 PM
Good Works Brewing
Dog Mom Day at Timber Hill Winery
Timber Hill Winery and Brown Paws Dog Rescue are teaming up to celebrate dog moms! Activities include: a dog mom market, permanent jewelry and matching dog collar charms, an agility course, dog nail painting, and more.
May 2, 2026
11:00 AM - 2:00 PM
Timber Hill Winery
Milton Public Library Food Truck Rally
Stop by for the annual Food Truck Rally! A percentage of the proceeds will go towards library services and programming.
May 3, 2026
11:00 AM - 2:00 PM
Milton Public Library
Milton Community Days Market at Parkview and College Street
This amazing event features over 90 vendors and food trucks! This open air evening market is the perfect place to shop and dine. Find crafters, makers, bakers, growers, and more.
May 8, 2026
5:00 - 8:00 PM
Parkview and College Street
May Fiesta at The Gathering Place
This fiesta features a taco bar, specialty drinks of Margaritas and Nada Coladas (non-alcoholic) and a performance by the Even Start Dancers of Beloit. Registration is required!
May 12, 2026
5:00 - 7:00 PM
The Gaterhing Place
Social Artworking at Milton Public Library
This is your chance to create with other artists and makers! Bring a current art project and supplies to SPARK. You’ll enjoy dedicated time to work on your project and great company.
May 12, 2026
6:00 - 7:00 PM
Milton Public Library
Veggie Planting with Geske’s Gardens at Good Works Brewing Company
Good Works Brewing Company is hosting a lively veggie planting class! You’ll learn how to plant easy veggies while enjoying a drink. Leave with your own planted veggies, solid growing tips, adn more. The cost for this event is $20.
May 17, 2026
1:00 - 3:00 PM
Good Works Brewing Company
Kitten Shower at Timber Hill Winery
Join Timber Hill Winery and the Humane Society of Southern Wisconsin to support kittens in need! You’ll meet adoptable kittens, enjoy wine, and more, This event is free but donations are encouraged.
May 17, 2026
2:00 - 5:00 PM
Timber Hill Winery