Fun Events to Explore in Milton, Wisconsin This December!
As the weather turns colder, the Milton community is heating up with fun events! If you’re looking for something fun to do this December, we’ve got you covered. Here’s a list of exciting occasions going on this month:
Gossip Girl Trivia at Timber Hill Winery
Hey Wisconsinites, Gossip Girl here…
Spotted: You, proving you’re the real Queen B of trivia. If you’ve got a thorough knowledge of the show, check out this event at Timber Hill Winery! XOXO…
December 5, 2025 6:00 PM - 7:00 PM
8220 N John Paul Road
Milton, WI 53563
Merry Milton Lighted Christmas Parade at Downtown Milton
Get the holiday season started with Milton’s annual Lighted Christmas Parade! The festivities will start at Arthur Drive and St. Mary’s Street, then continue on to Parkview Drive. It will conclude at North Goodrich Park. Bring the whole family!
December 5, 2025 7:00 PM
Downtown Milton
Milton, WI 53563
Haven’s Christmas Carol at Rubber Ducky Winery & Country Market
Ready for an immersive dining experience? This event is said to be, “a theatrical night of mystery, laughter, and handcrafted elixirs inside the historic 1870s Haven House.” Guests will enjoy a three-course meal along with three artisan cocktails as costumed actors bring the story to life around them. The cost for this event is $60 and advance registration is required.
December 6, 7, 19, and 20 at various times
232 S Janesville Street
Milton, WI 53563
Afternoon with Santa at The Gathering Green
The Gathering Green is putting on a fun-filled celebration with crafts, games, hot dogs, and a visit from Santa! Bring your loved ones and make memories at this free community celebration.
December 7, 2025 11:00 AM
715 Campus Street
Milton, WI 53563
Milton Community Tree Lighting
The Open Doors Foundation, along with The Chapel and local community friends are creating a cozy evening of lights, laughter, and togetherness at the Milton Community Tree Lighting. Along with the tree lighting ceremony, you can get photos with Santa, enjoy hot cocoa and concessions, create crafts, play Reindeer games, and more.
December 7, 2025 4:00 PM - 6:00 PM
North Goodrich Park
Milton, WI 53563
Show of Lights
We love to see Milton lit up every year with Christmas cheer! Drive around the community to see the hard work our neighbors put into decorating their homes and businesses. Vote for your favorite decorated house and business for extra fun!
December 7, 2025 4:00 PM - 8:00 PM
Various Locations
Milton, WI 53563
Photos with Santa at Timber Hill Winery
Looking for an easy way to capture the magic of Christmas? Stop at Timber Hill Winery for photos with Santa! You can get up to five digital images to savor for years to come. The cost for this event is $20.
December 14, 2025 11:30 AM - 1:30 PM
8220 N John Paul Road
Milton, WI 53563
Shopping at Sunny & Olive!
Looking for a fun, affordable shopping experience? Come down to Sunny & Olive! Since 2023, we’ve been curating the best secondhand finds and consignment treasures. Visit our shop for size-inclusive, sustainable fashion.
613 W Madison Ave
Milton, WI 53563