What’s Happening in Milton This October?
October in Milton is packed with events that make you want to grab your friends and throw on the coziest sweater. From treasure hunting at Vintage Shop Hop to sipping wine at trivia nights, there’s no shortage of fun. To make things easy, we pulled together a list of can’t-miss happenings around town.
Fall Vintage Shop Hop
Sunny & Olive is jumping back into Vintage Shop Hop. We can’t wait to see you! This three-day shopping road trip brings together 400+ small businesses across Wisconsin and Illinois.
You’ll find us in our historic feed mill, where we’ve got not one but two full floors of lightly used, secondhand consigned clothing just waiting to be discovered. Plus, we share our space with Red Rooster and Peddlar’s Loft, so you can make a whole afternoon of it.
All weekend long, we’re sweetening the deal with 15% off your entire order. We’ll be open Friday through Sunday, 10 AM – 5 PM, so make sure Sunny & Olive is one of your first (and favorite) stops. Then, keep the treasure hunt going with all the other amazing shops on the route.
For the full list of participating shops, follow Vintage Shop Hop on Facebook. See you there!
October 3-5, 2025 10:00 AM - 5:00 PM
613 W Madison Avenue
Milton, WI
Fall Fest Market Craft and Vendor Fair at Chapel Specialties on the Square
This cozy craft fair features great gift items, home decor, and more! While you browse, fuel up with concessions that keep the day feeling festive. (Because shopping is always better with a snack in hand).
October 4, 2025 9:00 AM - 3:00 PM
880 McEwan Lane
Milton, WI
Vine to Bine Fun Run and Dog Walk at Timber Hill Winery
The second annual Vine to Bine Fun Run and Dog Walk is here! You’ll kick things off at Timber Hill Winery, then run, walk or casually stroll your way to Good Works Brewing Company for an Oktoberfest celebration. All fitness levels are welcome and costumes are encouraged. Break out that lederhosen or dirndls!
October 4, 2025 10:30 AM - 4:30 PM
8220 N John Paul Rd
Milton, WI
Chunky Knit Blanket Workshop at Good Works Brewing Company
A drink in your hand, yarn in your lap, and all the cozy vibes. Sign us up! This workshop is all about creating your own chunky knit blanket. But don’t worry, there are no needles and no stress. All you need is your hands and a little guidance! Everyone from beginners to season knitters are welcome to attend.
October 4, 2025 12:00 PM - 4:00 PM
237 Parkview Drive
Milton, WI
Goat Yoga at Triple H Ranch
Yoga is good. Yoga with goats is even better. This class blends movement, mindfulness, and a little chaos courtesy of some very adorable four-legged friends. Beyond the smiles and stress relief, your registration supports the amazing therapeutic programming Triple H Ranch offers for both kids and adults. The cost for this event is $30.
October 5, 2025 11:00 AM - 12:00 PM
5405 N Kennedy Road
Milton, WI
Pumpkin Fest at The Gathering Place
Fall family fun = unlocked. The Gathering Place is rolling out a day packed with crafts, games, costumes, and — you guessed it — pumpkins. Bring the whole crew for afternoon fun!
October 5, 2025 11:00 AM
715 Campus Street
Milton, WI
Milton Community Days at Goodrich Square
Treasure hunt meets block party! With more than 90 vendors and food trucks, this open-air evening market has everything. From handmade crafts to local art and baked goods, you’ll find it all.
October 10, 2025 5:00 PM - 8:00 PM
Parkview and College Street
Milton, WI
Taylor Swift Trivia at Timber Hill Winery
Swifties, this one’s for you. Test your lyric recall, album knowledge, and memory of Taylor’s most iconic moments. Bring your crew, sip some wine, and battle it out for bragging rights.
October 10, 2025 6:00 PM - 7:00 PM
8220 N John Paul Road
Milton, WI
Junction Function at Merchant Row
If “good food, good music, good vibes” had a hometown festival, this would be it. Junction Function is serving up a full day of flavor and fun with a BBQ competition, bake-off, beer tent, live music, and family-friendly activities.
Competitors for the BBQ competition will be going head-to-head for $500 for first place. $250 is up for grabs for the second place winner.
October 11, 2025 1:00 PM
Merchant Row
Milton, WI
Buckhorn Supper Club’s Lobster Boil and Costume Party
Get ready for dinner, dancing, and a little Halloween magic. Buckhorn Supper Club is hosting its annual Lobster Boil and Costume party! Enjoy lobster (of course), drinks, and live music from Ludy and his Lady Nicole. Costumes are encouraged and reservations are a must.
October 28, 2025 5:30 - 9:30 PM
11802 N Charley Bluff Road
Milton, WI
HalloWine Costume Party at Rubber Ducky Winery and Country Market
HalloWine night is all about fun, friends, and a little friendly costume competition. Prizes will be awarded for most original, best individual, best group, and scariest costume. Bring your A-game (and maybe a little fake blood or glitter, depending on your vibe).
October 31, 2025 6:30 PM - 9:30 PM
232 S Janesville Street
Milton, WI