Explore Milton: Fun-Filled June 2026 Events!
It’s officially summer and Milton, Wisconsin is popping off with fun-filled events. Below, you’ll find a round-up of all the best happenings in town! From relaxing yoga to community fundraising events, explore everything Milton has to offer.
Yoga in the Vineyard at Timber Hill Winery
Need to unwind? Timber Hill Winery has you covered. All abilities are welcome at this scenic yoga event.
June 4, 2026
5:30-6:30 PM
Timber Hill Winery
Grapes & Hops at KANDU Industries
This event has been an adored tradition for over a decade. But now, it has a new twist. Guests will experience a speakeasy theme while sampling specialty wine and beer poured by local celebrities. Feel free to dress the part for this roaring ‘20s vibe! All proceeds benefit KANDU’s mission of creating, promoting, and providing diverse opportunities for people with disabilities or disadvantages.
June 5, 2026
6:00-9:00 PM
KANDU Industries
Pub Trivia at Timber Hill Winery
Timber Hill Winery hosts the most engaging pub trivia nights! Head on down with your friends and experience a night of friendly competition and great drinks.
June 5, 2026
6:00-7:00 PM
Timber Hill Winery
Social Artworking at The Milton Public Library
Crafting doesn’t have to be lonely. Bring a current art project to social artworking at the Milton Public Library! You’ll connect with great local artists — and make progress on your current WIP.
June 9, 2026
6:00-7:00 PM
Milton Public Library
Writing Your Family History for the Non-Writer at The Milton House Museum
Everyone’s story deserves to be told. At this event, you’ll learn how to turn your research into a well-written family history.
June 9, 2026
6:30 PM
The Milton House Museum
Girls Night Out Rock County at Timber Hill Winery
Have fun, network, and support a great cause all in one night! This casual networking event benefits Triple H Ranch & Therapeutic Horsemanship with a selection of raffle items. The event is free, but bring your wallet for refreshments and raffle opportunities.
June 10, 2026
5:00-8:00 PM
Timber Hill Winery
Painted Wine Glass Workshop at Timber Hill Winery
Sick of boring old wine glasses? Us too. At Timber Hill Winery, you can hand paint your very own custom set. You’ll be guided through a featured design. Or, you can bring your own inspiration and choose your own colors. All supplies are included, but spots are limited! Register today.
June 16, 2026
5:00-7:00 PM
Timber Hill Winery
Milton Community Days Market
The Milton Community Days Market is back! Explore over 90 vendors and food trucks at this open air evening event. Find crafters, makers, bakers, growers, and more.
June 19, 2026
5:00-8:00 PM
Parkview and College Street
Bookish Vibes Night at Sunny & Olive
Calling all book babes! Sunny & Olive is hosting the ultimate bookish event. Stop by the shop to explore what local book stores have to offer.
June 25, 2026
5:00-8:00 PM
Sunny & Olive
Land of the Giants Open Garden Days at Land of the Giants Hosta Farm
Don’t miss your chance to explore this hidden gem! Land of the Giants Hosta Farm offers online sales, with occasional open garden days where you can shop their selection. In their three acres of shade gardens, you’ll find over 340,000 hostas, including many rare and unique varieties.
June 27, 2026
9:00 AM - 3:00 PM
Land of the Giants Hosta Farm
Cake Pop and Dirty Soda Pairing at Timber Hill Winery
What could be better than a cake pop and dirty soda? Visit Timber Hill Winery for the ultimate pairing event.
June 30, 2026
5:30-6:30 PM
Timber Hill Winery