What’s Going on in Milton? September 2025 Edition
September in Milton is packed with fun things to do! The air’s a little crisper and the town is buzzing with events that make you want to go out and live your best local life. From brunches that make you feel like a queen, to live music, craft workshops and even a little friendly competition, Milton in September has a little something for everyone. And since Sunny & Olive is all about celebrating local vibes, we’ve rounded up all the events you absolutely cannot miss. Let’s dive in!
Back to School Brunch Grazing at Timber Hill Winery
Picture this: the kids are officially back in school, your house is (somewhat) quiet again, and you finally get the chance to breathe. What better way to celebrate surviving another summer of chaos than with a Back to School Brunch Grazing?
This is your chance to treat yourself to a morning that’s all about ease, good food, and a little sparkle in your glass. We’re talking a gorgeously curated grazing table (think all your brunch favorites laid out like a Pinterest dream), plus mimosas, wines, and more.
So grab your bestie, your mom squad, or just bring your fabulous self for a morning that feels like one big exhale. You’ve earned it!
September 2, 2025 11:00 AM - 1:00 PM
8220 N John Paul Rd
Milton, WI 53563
TV Then & Now Trivia Night at Good Works Brewing Company
How fun does this sound?? Starting in September, Good Works Brewing Company is turning the first Thursday of every month into the ultimate brain-flex-meets-hangout night. And no shade to the old-school trivia setups, but this one is way better. Think more interaction, less of that endless scribbling on paper, shorter rounds (bless), great prizes, and the right amount of friendly competition.
Some nights are even tied to local charities. You’re not only flexing your pop culture knowledge, you’re also doing some good while sipping a cold one. Love that for us. The first theme out of the gate is Whachu Watchin? TV Then & Now. Which basically means dust off your sitcom knowledge, rewatch that one show you binged in 48 hours, and maybe phone a friend who still remembers cable.
September 4, 2025 7:00 PM - 8:30 PM
237 Parkview Drive
Milton, WI 53563
Cars & Coffee at Main Street Market Piggly Wiggly
There’s just something about a Saturday morning that hits different when it starts with coffee, donuts, and the kind of cars that make you go “ohhh damn.”
From June through November, every first Saturday of the month is basically your excuse to roll out of bed, grab your friends/family/kids (there’s a bouncy house!) and head over to the Main Street Market Piggly Wiggly. You’ll find everything from vintage classics to sleek modern rides that feel like they’ve been pulled straight out of a Fast & Furious movie. Add in live music and entertainment and it’s the perfect Saturday starter pack.
September 6, 2025 8:00 AM - 11:00 AM
727 S Janesville Street
Milton, WI 53563
Fall Bingo Blitz at The Gathering Place
Hear me out: Bingo nights are criminally underrated. We all think of Bingo as something our grandparents drag us to, but nothing gets people more competitive than a chance to win cold, hard cash.
At The Gathering Place, the bar and concessions open at 5 PM (because obviously snacks and a drink in hand make you luckier. Don’t ask me for scientific proof, just trust the vibe.) Then, at 6:15 PM sharp, the games begin. You’ll have the chance to win cash prizes, a jackpot prize, 50/50 raffles, and more. Oh, and it’s just $1 per game card which is like…cheaper than your iced coffee habit and way more thrilling.
September 6, 2025
715 Campus Street
Milton, WI 53563
Haunted House Workshop at Chapel Specialties on the Square
Halloween crafts >>> literally everything else. Sorry, I don’t make the rules. Join Deanna for a hands-on workshop where you’ll get to build your very own haunted paper house using the Stampin’ Up! Haunted Home Kit. This kit comes with everything you need to create your very own haunted paper house. (HGTV but make it ghostly.)
You’ll follow the step-by-step instructions to put the house together, then add your own creepy-cute flair to it. Deanna’s bringing the know-how (and snacks, bless her.) Glue guns will be available, but if you have your own ride-or-die one, bring it! All you have to do is show up ready to craft. Cost is $22 per person.
September 7, 2025 1:00 PM - 4:00 PM
819 E High Street
Milton, WI 53563
Business After 5 at Milton Public Library
Business events can sometimes feel…stiff. But Business After 5 is a totally different vibe. Hosted by the Milton Area Chamber of Commerce and the Milton Public Library, this evening is all about connection. You’ll get the chance to network, explore local businesses, and hang out in a setting that’s built for conversation.
September 9, 2025 5:00 PM - 7:00 PM
430 E High Street
Milton, WI 53563
Milton Community Days at Goodrich Square
Picture this: a summer evening, the air buzzing with music and chatter, the smell of something delicious wafting from a food truck, and rows upon rows of booths just waiting to be explored. That’s exactly the vibe at this open-air evening market — and honestly, it’s the perfect night out.
With over 90 vendors (full-on treasure-hunt status), you’ll get great finds from an array of crafters, makers, bakers, growers, and more. Bring your friends, bring your family, or just bring yourself and wander! This market is all about discovering new favorites, supporting local makers, and soaking up that perfect evening energy.
September 12, 2025 5:00 PM - 8:00 PM
Parkview and College Street
Milton, WI 53563
Milton House Museum Signature Event at Buckhorn Supper Club
The Milton House is Wisconsin’s only certified Underground Railroad site that’s open to the public. That means every brick and every corner carries a piece of history that deserves to be remembered and shared. This event is your chance to be part of protecting that legacy.
This is a fundraiser dedicated to preserving one of Wisconsin’s most extraordinary landmarks. Your support helps protect this legacy, share it with future generations, and ensure that the powerful story of Freedom Seekers continues to inspire. The cost is $250 per person for the main event; $100 per person for dinner only.
September 13, 2025 1:30 PM - 8:30 PM
11802 N Charley Bluff Road
Milton, WI 53563
Goat Yoga at Triple H Ranch
Who decided yoga needed to be so serious all the time?? Enter: goat yoga. It’s the perfect mashup of movement, mindfulness, and baby goats who don’t care if your downward dog looks more like a sad plank.
You’ll get all the benefits of a solid yoga session (stress relief, boosted mood, a little extra flexibility to impress yourself later), plus the undeniable joy of hanging out with goats. They climb, they cuddle, they sometimes nibble your shoelaces…It’s chaos, it’s therapy, it’s everything. Cost is $30 per person.
September 14, 2025
5405 N Kennedy Road
Milton WI 53563
Milton Annual Waterway Cleanup
We all love a good day at the park by the water…until you spot the plastic bag floating by or that random crushed soda can that’s been living on the trail since 2004. Not the vibe. Now, you can do something about it! The Protect Wisconsin Waterways Annual Waterway Clean-Up is your chance.
Work side by side with other awesome humans to clear out trash so our local spaces stay clean, safe, and beautiful. It feels good to know you’re leaving things better than you found them.
September 20, 2025 8:00 AM - 10:00 AM
301 W High Street
Milton, WI 53563
Fish Boil at Timber Hill Winery
Pairing up with Timber Hill Winery, the legendary Fitzgerald’s Genoa Junction is putting on a one-night-only experience you won’t forget. On the menu is a traditional fish boil, honey BBQ chicken (for the non-fish people, we see you) and dessert to close out the night.
And because food always tastes better with vibes, there’ll be live music and plenty of Timber Hill wines to sip while you soak it all in. The boilover happens at 6 PM sharp. Tickets are limited and registration is required. Cost is $65 per person.
September 20, 2025 5:00 PM - 8:00 PM
8220 N John Paul Road
Milton, WI 53563
Oktoberfest at KANDU
KANDU’s Oktoberfest is back! Hundreds of people come together to celebrate the season with live music from the crowd-favorite Nauti-Nauti band, food trucks serving up food you’ll still be thinking about next week, local beer and wine flowing, and plenty of dancing to keep you warm.
Every beer you sip, every brat you devour, every dance move you’ll regret later — it all goes right back into supporting KANDU’s mission. That means creating opportunities, independence, and possibility for people with disabilities or disadvantages.
September 27, 2025 3:00 PM - 6:00 PM
15 S Plumb Street
Milton, WI 53563
Keep Up with What’s Going on in Milton, WI!
So there you have it — your full-on guide to making September in Milton one for the books. Take your time, explore, and soak in everything our little town has to offer. And hey, after you’ve had your fun, swing by Sunny & Olive. What’s a perfect September outing without a little consignment treasure hunting to top it off?